n-methyl-3,4-methylenedioxyamphetamine profile

N-Methyl-3,4-methylenedioxyamphetamine: An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3,4-methylenedioxymethamphetamine : A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	1615
CHEMBL ID	43048
CHEBI ID	1391
SCHEMBL ID	44210
MeSH ID	M0028171

Synonym
KBIO1_000962
DIVK1C_000962
1-(1,3-benzodioxol-5-yl)-n-methyl-2-propanamine
CHEBI:1391 ,
n,alpha-dimethyl-1,3-benzodioxole-5-ethanamine
1-(1,3-benzodioxol-5-yl)-n-methylpropan-2-amine
PDSP2_001506
IDI1_000962
dea no. 7405
(rs)-3,4-(methylenedioxy)methamphetamine
(+-)-n-methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane
3,4-methylenedioxy-n,alpha-dimethyl-beta-phenylethylamine
(+-)-(3,4-methylenedioxy)methamphetamine
XTC ,
ecstasy
1,3-benzodioxole-5-ethanamine, n,alpha-dimethyl-
dl-(3,4-methylenedioxy)methamphetamine
phenethylamine, n,alpha-dimethyl-3,4-methylenedioxy-
hsdb 6929
(+-)-n-methyl-3,4-(methylenedioxy)amphetamine
methylenedioxymethamphetamine
n-methyl-3,4-methylenedioxyamphetamine
mdma
42542-10-9
C07577
3,4-methylenedioxymethamphetamine
DB01454
midomafetamine
PDSP1_001522
NINDS_000962
NCGC00168266-01
methylenedioxymetamphetamine
methylenedioxy methamphetamine
CHEMBL43048 ,
3,4-methylenedioxymetamphetamine
methylenedioxymethamfetamine
bdbm50010588
NCGC00168266-02
AKOS006283463
ccris 9277
ke1sen21rm ,
molly [street name]
xtc [street name]
unii-ke1sen21rm
midomafetamine [usan]
mandy [street name]
EPITOPE ID:178091
mandy
(+/-)-(3,4-methylenedioxy)methamphetamine
midomafetamine [who-dd]
n-methyl-3,4-methylenedioxyamphetamine [hsdb]
(rs)-1-(benzo(d)(1,3)dioxol-5-yl)-n-methylpropan-2-amine
(+/-)-n,.alpha.-dimethyl-3,4-(methylenedioxy)phenethylamine
1,3-benzodioxole-5-ethanamine, n,.alpha.-dimethyl-
phenethylamine, n,.alpha.-dimethyl-3,4-methylenedioxy-
(+/-)-n-methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane
54946-52-0
d,l-3,4-methylenedioxymethamphetamine
mdma [mi]
midomafetamine [inn]
molly
methylenedioxymethamfetamine [mart.]
gtpl4574
[1-(2h-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine
SCHEMBL44210
3,4-mdma
rac-mdma (rac-3,4-methylenedioxymethamphetamine) 1.0 mg/ml in methanol
mdma (ecstasy)
3,4-methylenedioxy-n-methylamphetamine
(+/-)-3,4-methylenedioxymethamphetamine
(+/-)-n-methyl-3,4-(methylenedioxy)amphetamine
DTXSID90860791 ,
Q69488
midomafetamine (usan/inn)
D11172
dtxcid70197310
xtc (street name)
methylenedioxymethamfetamine (mart.)
mandy (street name)
midomafetaminum
molly (street name)
midomafetamina

Research Excerpts

Toxicity

Excerpt	Reference	Relevance
"The risk of adverse reactions to 3,4-methylenedioxymethamphetamine (MDMA), more commonly known as "ecstasy", is now widely known in both the USA and UK, but the patterns of illness remain varied."	( Toxicity and deaths from 3,4-methylenedioxymethamphetamine ("ecstasy") Dawling, S; Henry, JA; Jeffreys, KJ, 1992)	0.28
"Regulation of neurotoxicants is generally based on setting allowable doses (exposures) by dividing a no observed adverse effect level (NOAEL) by uncertainty factors that hopefully account for interspecies and intraspecies differences for extrapolations of experimental results obtained in animals to humans."	( Risk assessment for neurotoxic effects. Gaylor, DW; Slikker, W, 1990)	0.28
" However, a comparison of the relative toxic effects of MDMA and MBDB indicates that MBDB may be slightly less neurotoxic."	( Neurotoxic effects of the alpha-ethyl homologue of MDMA following subacute administration. Johnson, MP; Nichols, DE, 1989)	0.28
" The central monoamine stores of rats were significantly decreased with reserpine (5 mg/kg) prior to toxic injections of MDMA."	( Reserpine does not prevent 3,4-methylenedioxymethamphetamine-induced neurotoxicity in the rat. Hekmatpanah, CR; McKenna, DJ; Peroutka, SJ, 1989)	0.28
"Using the systemically active, non-competitive N-methyl-D-aspartate (NMDA) receptor antagonist dextrorphan, we explored the role of the NMDA receptor-calcium channel complex in the toxic mechanism of action of 3,4-methylenedioxymethamphetamine (MDMA)."	( The N-methyl-D-aspartate (NMDA) receptor antagonist, dextrorphan, prevents the neurotoxic effects of 3,4-methylenedioxymethamphetamine (MDMA) in rats. Finnegan, KT; Irwin, I; Langston, JW; Skratt, JJ, 1989)	0.28
" Perhaps as a consequence of this, the toxic effects of MDMA in the monkey involve serotonergic nerve fibers as well as cell bodies, whereas in the rat, only nerve fibers are affected."	( Studies of MDMA-induced neurotoxicity in nonhuman primates: a basis for evaluating long-term effects in humans. Ricaurte, GA, 1989)	0.28
" MDMA was either equally toxic or slightly to moderately less toxic than its close congener, MDA, (+/-)-3,4-methylenedioxyamphetamine."	( Toxicity of MDA (3,4-methylenedioxyamphetamine) considered for relevance to hazards of MDMA (Ecstasy) abuse. Davis, WM; Hatoum, HT; Waters, IW, 1987)	0.27
"This study compared the toxic effects of oral versus subcutaneous and single versus multiple doses of 3,4-methylenedioxymethamphetamine (MDMA) on central serotonergic neurons in non-human primates."	( Toxic effects of MDMA on central serotonergic neurons in the primate: importance of route and frequency of drug administration. DeLanney, LE; Irwin, I; Langston, JW; Ricaurte, GA, 1988)	0.27
" None of the protective drugs inhibited the initial 5-HT loss following MDMA, rendering unlikely any proposal that they are protective because they inhibit 5-HT release and the subsequent formation ofa toxic indole derivative."	( A study of the mechanism of MDMA ('ecstasy')-induced neurotoxicity of 5-HT neurones using chlormethiazole, dizocilpine and other protective compounds. Colado, MI; Green, AR, 1994)	0.29
" The third step is to define an adverse level for a response so that the probability (risk) of exceeding that level can be estimated as a function of dose."	( Modeling for risk assessment of neurotoxic effects. Gaylor, DW; Slikker, W, 1994)	0.29
"Methamphetamine and MDMA as well as similar substituted phenethylamines are toxic to DA and/or 5-HT neurons."	( Methamphetamine and methylenedioxymethamphetamine neurotoxicity: possible mechanisms of cell destruction. Sabol, KE; Seiden, LS, 1996)	0.29
" Together with the results of the N(G)-monomethyl-L-arginine and N(G)-nitro-L-arginine experiments, the data suggest that NO plays little or no role in the toxic mechanism of action of METH or MDMA."	( Nitric oxide and the neurotoxic effects of methamphetamine and 3,4-methylenedioxymethamphetamine. Finnegan, KT; Taraska, T, 1997)	0.3
"A sample of drug users (n = 158) were contacted and interviewed in non-clinical community settings about their use of Ecstasy, cocaine powder, and amphetamines and the adverse effects of these drugs."	( Adverse effects of stimulant drugs in a community sample of drug users. Fountain, J; Gossop, M; Griffiths, P; Powis, B; Strang, J; Williamson, S, 1997)	0.3
" Up to now, no death could be attributed to MDMA intoxication only because our analyses always revealed the additional presence of toxic amounts of other psychoactive drugs (e."	( [Ecstasy--the status in French-speaking Switzerland. Composition of seized drugs, analysis of biological specimens and short review of its pharmacological action and toxicity]. Augsburger, M; Giroud, C; Rivier, L; Sadeghipour, F; Varesio, E; Veuthey, JL, 1997)	0.3
"The toxic effects of methamphetamine (METH) (2."	( Differential toxic effects of methamphetamine (METH) and methylenedioxymethamphetamine (MDMA) in multidrug-resistant (mdr1a) knockout mice. Cadet, JL; Hirata, H; Ladenheim, B; Mann, H; Moran, TH, 1997)	0.3
" Reduced glutathione (GSH), adenosine-5'-triphosphate (ATP) and lipid peroxidation were investigated to evaluate the toxic effect of MDMA, in vitro, using freshly isolated rat hepatocytes."	( 3,4-Methylenedioxymethamphetamine (ecstasy)-induced hepatotoxicity: effect on cytosolic calcium signals in isolated hepatocytes. Beitia, G; Cenarruzabeitia, E; Cobreros, A; Sainz, L, 1999)	0.3
" The toxic effect of MDMA was also observed in other hepatic processes."	( Ecstasy-induced toxicity in rat liver. Beitia, G; Cenarruzabeitia, E; Cobreros, A; Sainz, L, 2000)	0.31
" In the present paper, we review the extensive body of data demonstrating that MDMA produced toxic effects on brain 5-HT neurons in animals and present new data indicating that levels of the type 2 vesicular monoamine transporter are reduced in MDMA-treated animals, providing further indication of MDMA's 5-HT neurotoxic potential."	( (+/-)3,4-Methylenedioxymethamphetamine ('Ecstasy')-induced serotonin neurotoxicity: studies in animals. McCann, UD; Ricaurte, GA; Yuan, J, 2000)	0.31
" There are many methodological problems and uncertainties with research in this field: non-random allocation of subjects to drug conditions, the deleterious effects of other psychoactive drugs, and the possibility that these adverse profiles reflect pre-existing personality characteristics in Ecstasy users."	( Human research on MDMA (3,4-methylene- dioxymethamphetamine) neurotoxicity: cognitive and behavioural indices of change. Parrott, AC, 2000)	0.31
" However, reports of adverse effects and fatalities have increased in the medical and popular press."	( Agony and ecstasy: a review of MDMA effects and toxicity. Burgess, C; Gill, M; O'Donohoe, A, 2000)	0.31
" Adverse effects include hyperthermia, seizures, cardiac arrhythmias, hepatotoxicity, hyponatraemia and many psychiatric disorders."	( Agony and ecstasy: a review of MDMA effects and toxicity. Burgess, C; Gill, M; O'Donohoe, A, 2000)	0.31
" Overall, these results highlight the importance of energy balance to the function of DA and 5-HT neurons and to the toxic effects of MDMA."	( Enhancement of 3,4-methylenedioxymethamphetamine neurotoxicity by the energy inhibitor malonate. Burrows, KB; Gudelsky, GA; Nixdorf, WL; Yamamoto, BK, 2001)	0.31
"The consumption of 3,4-methylenedioxymethamphetamine (ecstasy; MDMA) may cause hepatocellular damage in humans, a toxic effect that has been increasing in frequency in the last few years, although the underlying mechanisms are still unknown."	( Is hyperthermia the triggering factor for hepatotoxicity induced by 3,4-methylenedioxymethamphetamine (ecstasy)? An in vitro study using freshly isolated mouse hepatocytes. Bastos, ML; Carvalho, F; Carvalho, M, 2001)	0.31
" Administration of MDMA leads to the formation of metabolites responsible for its toxic effects on serotonergic neurons in rats and non-human primates and on dopaminergic neurons in mice."	( Involvement of free radicals in MDMA-induced neurotoxicity in mice. Cadet, JL; Jayanthi, S; Thiriet, N, 2001)	0.31
"The mechanism of 3,4-methylenedioxymethamphetamine (d-MDMA)-induced neurotoxicity may involve formation of toxic radical species."	( d-MDMA during vitamin E deficiency: effects on dopaminergic neurotoxicity and hepatotoxicity. Johnson, EA; Kisin, E; Kommineni, C; Miller, DB; O'Callaghan, JP; Shvedova, AA, 2002)	0.31
" MDMA and MDA were not found to be toxic to either rat or human PTCs at any concentration tested (100-800 micro M)."	( Role of metabolites in MDMA (ecstasy)-induced nephrotoxicity: an in vitro study using rat and human renal proximal tubular cells. Bastos, ML; Borges, F; Carvalho, F; Carvalho, M; Fernandes, E; Hawksworth, G; Milhazes, N; Monks, TJ, 2002)	0.31
" "Poisoned ecstasy" was widely reported by the media as being responsible for the adverse effects observed."	( Multiple toxicity from 3,4-methylenedioxymethamphetamine ("ecstasy"). Dargan, PI; Greene, SL; Jones, AL; Kerins, M; O'connor, N, 2003)	0.32
" Although generally regarded as relatively safe, several studies have suggested a toxic effect on brain neurons in animals and possibly in humans."	( [Plusridisciplinary approaches to understand the neutoxic effects of Ecstasy]. Noble, F; Roques, BP, 2003)	0.32
" These adverse events might be related to the neurotoxic effects of the drug."	( Methylenedioxymethamphetamine (MDMA, Ecstasy) neurotoxicity: cellular and molecular mechanisms. Cadet, JL; Lyles, J, 2003)	0.32
" Acute and severe toxic effects following MDMA ingestion include hyperthermia, arrhythmias, rhabdomyolisis, disseminated intravascular coagulation, hepatotoxicity and even death."	( Hyperkalemia in fatal MDMA ('ecstasy') toxicity. Quiroga, JM; Raviña, P; Raviña, T, 2004)	0.32
" The aims of the present in vitro study were: (1) to evaluate and compare the hepatotoxic effects of MDMA and one of its main metabolites, N-methyl-alpha-methyldopamine (N-Me-alpha-MeDA) and (2) to investigate the ability of antioxidants, namely ascorbic acid and N-acetyl-L-cysteine (NAC), to prevent N-Me-alpha-MeDA-induced toxic injury, using freshly isolated rat hepatocytes."	( The toxicity of N-methyl-alpha-methyldopamine to freshly isolated rat hepatocytes is prevented by ascorbic acid and N-acetylcysteine. Bastos, ML; Borges, F; Carvalho, F; Carvalho, M; Fernandes, E; Milhazes, N; Remião, F, 2004)	0.32
" In order to measure the toxic effects to the brain, rats were given equimolar doses of MDMA (40 mg/kg/day) and METH (32 mg/kg/day) in subcutaneously implanted osmotic minipumps for a period of 5 days, and in-vitro autoradiography using [3H]-paroxetine, [3H]-mazindol, [3H]-methylspiperone, and [3H]-flunitrazepam, was performed on brain sections."	( The neurotoxic effects of 3,4-methylenedioxymethamphetamine (MDMA) and methamphetamine on serotonin, dopamine, and GABA-ergic terminals: an in-vitro autoradiographic study in rats. Armstrong, BD; Noguchi, KK, 2004)	0.32
"This article summarizes the short-term physiological toxicity and the adverse behavioral effects of four substances (GHB, ketamine, MDMA, and Rohypnol) that have been used at latenight dance clubs."	( Acute toxic effects of club drugs. Gable, RS, 2004)	0.32
"Recent publications claim that the recreational drug ecstasy is considered to be safe by many or most ecstasy users, or by young people or the general public."	( Is ecstasy perceived to be safe? A critical survey. Gamma, A; Jerome, L; Liechti, ME; Sumnall, HR, 2005)	0.33
" These results extend our recent findings of additive toxic effects when METH is combined with MDMA."	( MDMA ('Ecstasy') and methamphetamine combined: order of administration influences hyperthermic and long-term adverse effects in female rats. Clemens, KJ; Cornish, JL; Hunt, GE; Li, KM; McGregor, IS, 2005)	0.33
" Previous studies suggest that ecstasy (3,4 methylene-dioxymethamphetamine, MDMA, XTC) is toxic toward brain serotonin axons, but most of these studies have serious methodological limitations."	( The Netherlands XTC Toxicity (NeXT) study: objectives and methods of a study investigating causality, course, and clinical relevance. Booij, J; De Win, MM; Den Heeten, GJ; Jager, G; Korf, DJ; Ramsey, NF; Reneman, L; Schilt, T; Van den Brink, W; Verhulst, FC; Vervaeke, HK, 2005)	0.33
" Finally, the dopamine transporter inhibitor GBR 12909 completely prevented dopamine neurotoxicity caused by the malonate/MDMA combination and reversed the exacerbating toxic effects of malonate on MDMA-induced 5-HT depletion without significantly altering the hyperthermic response."	( Studies on striatal neurotoxicity caused by the 3,4-methylenedioxymethamphetamine/ malonate combination: implications for serotonin/dopamine interactions. Aguirre, N; Goñi-Allo, B; Herv'as, I; Lasheras, B; Ramos, M, 2006)	0.33
" Clinically important toxic effects have been reported, including fatalities."	( Acute toxic effects of 'Ecstasy' (MDMA) and related compounds: overview of pathophysiology and clinical management. Hall, AP; Henry, JA, 2006)	0.33
" A mistaken belief that it is a safe drug of low toxicity and a long duration of action has led to its widespread popularity among teenagers and young adults in recent years."	( [Ecstasy toxicity]. Reingardiene, D, 2006)	0.33
" The acute effects stemming from this association, in tandem with the final potentiation of serotonergic terminals injury, provide evidence of the potentially greater long-term adverse effects of this particular recreational drug combination."	( Association of caffeine to MDMA does not increase antinociception but potentiates adverse effects of this recreational drug. Camarasa, J; Escubedo, E; Pubill, D, 2006)	0.33
" The results confirmed our hypothesis as the metabolite proved to be more than 100-fold more toxic than the parent compound 3,4-methylenedioxymethamphetamine."	( Influence of CYP2D6 polymorphism on 3,4-methylenedioxymethamphetamine ('Ecstasy') cytotoxicity. Bastos, Mde L; Boer, Dd; Branco, PS; Brulport, M; Carmo, H; Carvalho, F; Doehmer, J; Ferreira, LM; Hengstler, JG; Hermes, M; Krebsfaenger, N; Oesch, F; Remião, F; Schön, MR; Silva, R, 2006)	0.33
" Finally, taking into account that several different pathways could contribute to the overall MDMA toxicity and that HHMA and catechol-thioether conjugates 1-5 have not been undoubtedly established as in vivo toxic metabolites of MDMA, it can be suggested that these compounds could participate in the toxic effects of this drug through the efficiency of redox active quinonoid centers generating ROS."	( Bacterial plate assays and electrochemical methods: an efficient tandem for evaluating the ability of catechol-thioether metabolites of MDMA ("ecstasy") to induce toxic effects through redox-cycling. Blanco, M; Felim, A; Herrera, G; Largeron, M; Neudörffer, A; Urios, A, 2007)	0.34
" Their abuse is associated with severe neurologic and psychiatric adverse events including the development of psychotic states."	( Neurotoxicity of substituted amphetamines: molecular and cellular mechanisms. Cadet, JL; Jayanthi, S; Krasnova, IN; Lyles, J, 2007)	0.34
" We therefore determined (1) the LD50 of MDMA and MDA, (2) their hyperthermic effects, (3) the activities of liver CYP1A2 and CYP2D, (4) the liver microsomal metabolism of MDMA and MDA, (5) and the plasma concentrations of MDMA and its metabolites 3 h after giving male and female Sprague-Dawley (SD) rats MDMA (5 mg."	( Sprague-Dawley rats display metabolism-mediated sex differences in the acute toxicity of 3,4-methylenedioxymethamphetamine (MDMA, ecstasy). Crété, D; Debray, M; Declèves, X; Fonsart, J; Galons, H; Menet, MC; Noble, F; Scherrmann, JM, 2008)	0.35
" This case report indicates that even non-chronic MDMA use may cause subacute toxic encephalopathy in which the clinical evolution is paralleled by neuroimaging changes in specific cerebral areas."	( Hippocampal remodelling after MDMA neurotoxicity: a single case study. Amistà, P; Battaglia, M; Bertagnoni, GE; Carollo, C; Costanzo, R; Lupi, A; Martinuzzi, A; Nifosì, F; Perini, G; Toffanin, T; Vestri, A, 2009)	0.35
"Converging evidence was found for a specific toxic effect of ecstasy on serotonergic axons in the thalamus."	( Neurotoxic effects of ecstasy on the thalamus. Booij, J; de Win, MM; Heeten, GJ; Jager, G; Lavini, C; Olabarriaga, SD; Ramsey, NF; Reneman, L; Schilt, T; van den Brink, W, 2008)	0.35
"Intracerebroventricular injection of methylenedioxymethamphetamine (MDMA, ecstasy) in rats fails to reproduce long-term toxic effects observed after peripheral administration."	( [Metabolites of ecstasy and cytotoxicity effects]. Blanco, M; Felim, A; Fleury, MB; Largeron, M; Monnet, FP; Neudörffer, A, 2009)	0.35
"3, 4-Methylenedioxymethamphetamine (MDMA, "ecstasy") has toxic effects on serotonergic neurons in the brain."	( Study on the neuroprotective effect of fluoxetine against MDMA-induced neurotoxicity on the serotonin transporter in rat brain using micro-PET. Chyueh, SC; Hu, SH; Huang, WS; Huang, YY; Li, IH; Liao, MH; Liu, JC; Liu, RS; Ma, KH; Shen, LH; Shiue, CY, 2010)	0.36
" MMMA was not toxic in the bacterial assay, indicating that its toxicity is not related to increased oxidative stress."	( Synthesis and in vitro cytotoxicity profile of the R-enantiomer of 3,4-dihydroxymethamphetamine (R-(-)-HHMA): comparison with related catecholamines. Blanco, M; Felim, A; Herrera, G; Largeron, M; Neudörffer, A; O'Connor, JE, 2010)	0.36
"Metabolism plays an important role in the toxic effects caused by 3,4-methylenedioxymethamphetamine (MDMA)."	( Differential roles of phase I and phase II enzymes in 3,4-methylendioxymethamphetamine-induced cytotoxicity. Antolino-Lobo, I; Meulenbelt, J; Nijmeijer, SM; Scherpenisse, P; van den Berg, M; van Duursen, MB, 2010)	0.36
" Jaundice, hepatomegaly, centrilobular necrosis, hepatitis and fibrosis represent some of the adverse effects caused by MDMA in the liver."	( Mechanisms underlying the hepatotoxic effects of ecstasy. Bastos, ML; Carvalho, F; Carvalho, M; Pontes, H; Remião, F, 2010)	0.36
" The molecular mechanisms involved in the genesis of these toxic effects are not yet fully clarified, but the oxidative stress, excitotoxicity, and mitochondrial dysfunction appear to be causal events that converge to mediate MDMA-induced toxicity."	( MDMA toxicity and pathological consequences: a review about experimental data and autopsy findings. Bello, S; Fineschi, V; Neri, M; Riezzo, I; Turillazzi, E, 2010)	0.36
" We finally concluded that hyperthermia could potentiate MDMA induced liver toxicity probably through a mitochondrial/lysosomal toxic cross-talk in freshly isolated rat hepatocytes."	( Involvement of mitochondrial/lysosomal toxic cross-talk in ecstasy induced liver toxicity under hyperthermic condition. Eskandari, MR; Khajeamiri, AR; Kobarfard, F; Nosrati, M; Pourahmad, J, 2010)	0.36
" Little is known about toxic effects of MDMA and potential underlying molecular mechanisms in the developing brain."	( Neurotoxic effects of MDMA (ecstasy) on the developing rodent brain. Bendix, I; Brait, D; Dzietko, M; Endesfelder, S; Felderhoff-Mueser, U; Hansen, HH; Klaus, J; Sifringer, M, 2010)	0.36
" There were no drug-related serious adverse events, adverse neurocognitive effects or clinically significant blood pressure increases."	( The safety and efficacy of {+/-}3,4-methylenedioxymethamphetamine-assisted psychotherapy in subjects with chronic, treatment-resistant posttraumatic stress disorder: the first randomized controlled pilot study. Doblin, R; Jerome, L; Mithoefer, AT; Mithoefer, MC; Wagner, MT, 2011)	0.37
"The dependent variable was the number of reported ecstasy-related adverse effects."	( Modelling the adverse effects associated with ecstasy use. Fisk, JE; Hadjiefthyvoulou, F; Montgomery, C; Murphy, PN, 2011)	0.37
"The number of adverse effects was associated positively with life-time exposure to ecstasy and negatively with period of abstinence from the drug."	( Modelling the adverse effects associated with ecstasy use. Fisk, JE; Hadjiefthyvoulou, F; Montgomery, C; Murphy, PN, 2011)	0.37
"Greater life-time exposure to ecstasy and consuming the drug concurrently with alcohol increase the likelihood of experiencing adverse effects, including paranoia, poor general health, irritability, confusion and moodiness."	( Modelling the adverse effects associated with ecstasy use. Fisk, JE; Hadjiefthyvoulou, F; Montgomery, C; Murphy, PN, 2011)	0.37
" In a forward genetic screen, we identified a mutant resistant to the toxic effects of dopamine."	( A Caenorhabditis elegans p38 MAP kinase pathway mutant protects from dopamine, methamphetamine, and MDMA toxicity. McIntire, SL; Schreiber, MA, 2011)	0.37
" Many people (ab)use BZP-based party pills usually without any significant toxic effects."	( Nephrotoxicity of recreational party drugs. Berney-Meyer, L; Putt, T; Schollum, J; Walker, R, 2012)	0.38
"The dissociation between subjective perceptions and objective performance decrements are important notions for traffic safety since this may affect a driver's judgement of whether or not it is safe to drive."	( Effects of alcohol (BAC 0.5‰) and ecstasy (MDMA 100 mg) on simulated driving performance and traffic safety. Brookhuis, KA; de Waard, D; Jantos, R; Molmans, BH; Skopp, G; Veldstra, JL; Verstraete, AG, 2012)	0.38
"3,4-Methylenedioxymethamphetamine (MDMA) induces both acute adverse effects and long-term neurotoxic loss of brain 5-HT neurones in laboratory animals."	( Lost in translation: preclinical studies on 3,4-methylenedioxymethamphetamine provide information on mechanisms of action, but do not allow accurate prediction of adverse events in humans. Fone, KC; Green, AR; King, MV; Shortall, SE, 2012)	0.38
" These data identify a new class of therapeutic in Parkinson's disease and highlight the potential benefits of studying illicit drugs that in themselves would never be considered safe for long-term therapy."	( A novel MDMA analogue, UWA-101, that lacks psychoactivity and cytotoxicity, enhances L-DOPA benefit in parkinsonian primates. Brotchie, JM; Fox, SH; Gandy, MN; Gomez-Ramirez, J; Huot, P; Johnston, TH; Lee, J; Lewis, KD; Martin-Iverson, M; McIldowie, M; Millar, Z; Nash, JE; Piggott, MJ; Salomonczyk, D; Thiele, S; Wagg, K; Yong-Kee, CJ, 2012)	0.38
" suggest that animal data could not be used to predict the adverse effects of 3,4-methylenedioxymethamphetamine (MDMA) in humans and that MDMA did not produce 5-HT neurotoxicity in the human brain."	( MDMA and 5-HT neurotoxicity: the empirical evidence for its adverse effects in humans - no need for translation. Parrott, AC, 2012)	0.38
" While it is known that their abuse could result in adverse health complications, including neurotoxicity, both the environmental conditions and activity states associated with their intake could strongly enhance drug toxicity, often resulting in life-threatening health complications."	( Environmental conditions modulate neurotoxic effects of psychomotor stimulant drugs of abuse. Kiyatkin, EA; Sharma, HS, 2012)	0.38
" In conclusion, MDMA catechol metabolites promote differential toxic effects to differentiated dopaminergic human SH-SY5Y cells."	( Neurotoxicity of "ecstasy" and its metabolites in human dopaminergic differentiated SH-SY5Y cells. Bastos, ML; Branco, PS; Capela, JP; Carvalho, F; Costa, VM; Fernandes, E; Ferreira, LM; Ferreira, PS; Meisel, A; Nogueira, TB, 2013)	0.39
" MDMA is toxic to both the serotonergic neurons and dopaminergic system."	( Effects of adenosine A2a receptor agonist and antagonist on hippocampal nuclear factor-kB expression preceded by MDMA toxicity. Ebrahimzadeh, A; Haghir, H; Kermanian, F; Mehdizadeh, M; Soleimani, M, 2013)	0.39
" These outcomes suggest that MDMA metabolism has hazard implications to liver cells even when metabolites are found in low concentrations, as they contribute additively to the overall toxic effect of MDMA."	( Mixtures of 3,4-methylenedioxymethamphetamine (ecstasy) and its major human metabolites act additively to induce significant toxicity to liver cells when combined at low, non-cytotoxic concentrations. Carmo, H; Carvalho, F; da Silva, DD; Silva, E, 2014)	0.4
" We showed that MDMA metabolites exhibited toxicity to SH-SY5Y differentiated cells, being the GSH and NAC conjugates more toxic than their catecholic precursors and MDMA."	( "Ecstasy"-induced toxicity in SH-SY5Y differentiated cells: role of hyperthermia and metabolites. Barbosa, DJ; Bastos, ML; Branco, PS; Capela, JP; Carvalho, F; Fernandes, E; Ferreira, LM; Silva, R, 2014)	0.4
" Furthermore, MDMA and MDMA-analogs have shown to have induced several adverse effects."	( Elucidating the neurotoxic effects of MDMA and its analogs. Ahuja, M; Bhattacharya, D; Clark, R; Deruiter, J; Dhanasekaran, M; Karuppagounder, SS; Suppiramaniam, V, 2014)	0.4
" These toxic effects include hyperthermia, hypotonic hyponatremia due to its arginine vasopressin secretagogue-like effects, rhabdomyolysis, and cardiovascular collapse."	( Nephrotoxic effects of common and emerging drugs of abuse. Herlitz, LC; Niles, JL; Pendergraft, WF; Rosner, M; Thornley-Brown, D, 2014)	0.4
" In conclusion, the study suggests a potentially dangerous effect of concomitant caffeine and mephedrone, and highlights the importance of taking polydrug use into consideration when investigating the acute adverse effect profile of popular recreational drugs."	( Caffeine alters the behavioural and body temperature responses to mephedrone without causing long-term neurotoxicity in rats. Fone, KC; Green, AR; King, MV; Shortall, SE, 2016)	0.43
" It produces serious adverse effects, but its pharmacological profile is not well recognized."	( Neurotoxic Effects of 5-MeO-DIPT: A Psychoactive Tryptamine Derivative in Rats. Gołembiowska, K; Kamińska, K; Kreiner, G; Noworyta-Sokołowska, K; Rogóż, Z, 2016)	0.43
" The MAO inhibitors clorgyline and deprenyl, and the SERT inhibitor fluoxetine, per se or in combination, were not able to mimic the toxic effects of MDMA in the P19-derived neurons or block the MDMA-induced cell toxicity."	( Non-Serotonergic Neurotoxicity by MDMA (Ecstasy) in Neurons Derived from Mouse P19 Embryonal Carcinoma Cells. Forsblad, A; Hashemian, S; Jacobsson, SO; Popova, D, 2016)	0.43
" Acute and subacute adverse effects of MDMA as assessed by the List of Complaints were dose-dependent and more frequent in females."	( Safety pharmacology of acute MDMA administration in healthy subjects. Liechti, ME; Vizeli, P, 2017)	0.46
" The toxic effects of 5-MAPB were greater than those of MDMA."	( Preventive effects of fructose and N-acetyl-L-cysteine against cytotoxicity induced by the psychoactive compounds N-methyl-5-(2-aminopropyl)benzofuran and 3,4-methylenedioxy-N-methamphetamine in isolated rat hepatocytes. Inomata, A; Nakagawa, Y; Suzuki, T, 2018)	0.48
" However, its potential for adverse effects such as hyperthermia and neurotoxicity may limit its clinical viability."	( Separating the agony from ecstasy: R(-)-3,4-methylenedioxymethamphetamine has prosocial and therapeutic-like effects without signs of neurotoxicity in mice. Curry, DW; Daoud, GE; Howell, LL; Tran, AN; Young, MB, 2018)	0.48
" This review discusses both the short- and long-term effects of 3,4-methylenedioxy-methamphetamine including methods by which some of these adverse effects can be prevented or even reversed to increase the safety of the commonly used drug."	( Is the recreational use of 3,4-methylenedioxy-methamphetamine safe? Boote, T, 2018)	0.48
" These results are in line with the hypothesis that activation of the NO cascade participates in the toxic effects induced by MDMA in the dopaminergic nigrostriatal system."	( Repeated Administration of 3,4-Methylenedioxymethamphetamine (MDMA) Elevates the Levels of Neuronal Nitric Oxide Synthase in the Nigrostriatal System: Possible Relevance to Neurotoxicity. Costa, G; Morelli, M; Simola, N, 2018)	0.48
" The present study aimed to evaluate the differential toxic effects of MDMA in adolescent and aged Wistar rats, using doses pharmacologically comparable to humans."	( Aged rats are more vulnerable than adolescents to "ecstasy"-induced toxicity. Barbosa, DJ; Bastos, ML; Capela, JP; Carvalho, F; Costa, VM; Duarte, JA; Duarte-Araújo, M; Feio-Azevedo, R; Fernandes, E; Gomes, S; Marques, F; Pereira, FC; Pita, I; Teixeira-Gomes, A, 2018)	0.48
" The present study showed strong cytotoxic potential for the NPS 5F-PB-22 and MDAI, moderate effects for MDMA, MDPV, methylone, cathinone, 4-MEC, and mephedrone, and no toxic effects for methamphetamine."	( Cytotoxicity of new psychoactive substances and other drugs of abuse studied in human HepG2 cells using an adopted high content screening assay. Beck, A; Flockerzi, V; Maurer, HH; Meyer, MR; Richter, LHJ, 2019)	0.51
" There have been no serious adverse events related to MDMA, no unexpected physiological responses to the MDMA sessions or changes to blood results or electrocardiograms, measured before and after the 8-week course."	( First study of safety and tolerability of 3,4-methylenedioxymethamphetamine (MDMA)-assisted psychotherapy in patients with alcohol use disorder: preliminary data on the first four participants. Nutt, D; O'Brien, S; Sakal, C; Sessa, B, 2019)	0.51
" However, a serotonin syndrome is not always followed by serotonergic injury, indicating different mechanisms responsible for two adverse effects."	( Differential role of dose and environment in initiating and intensifying neurotoxicity caused by MDMA in rats. Callanan, JJ; Ma, Z; Shields, CJ; Shokry, IM; Tao, R, 2019)	0.51
" It is concluded that the two adverse events utilize distinctly different mediating molecules during the toxic initiation and intensification."	( Differential role of dose and environment in initiating and intensifying neurotoxicity caused by MDMA in rats. Callanan, JJ; Ma, Z; Shields, CJ; Shokry, IM; Tao, R, 2019)	0.51
"3,4-Methylenedioxymethamphetamine (MDMA, ecstasy) has become a popular recreational drug of abuse among young adults, partly because of the belief that it is relatively safe compared with other drugs with the same stimulant and hallucinogenic effects."	( MDMA-Associated Liver Toxicity: Pathophysiology, Management, and Current State of Knowledge. Cajanding, RJM, 2019)	0.51
" However, evidence indicates that exposure to toxic doses of MDMA can lead to long-lasting dysregulation of brain monoaminergic neurotransmitters, primarily from studies conducted in young adult rodents."	( The acute toxic and neurotoxic effects of 3,4-methylenedioxymethamphetamine are more pronounced in adolescent than adult mice. Bagwell, MS; Chitre, NM; Murnane, KS, 2020)	0.56
" One of such drugs is MDMA (3,4-methylenedioxymethamphetamine) or ecstasy due to its high consumption in relevant age and sex groups and its adverse effects on human and rodent developing brains."	( Developmental neurotoxicity of MDMA. A systematic literature review summarized in a putative adverse outcome pathway. Barenys, M; Fritsche, E; Gómez-Catalán, J; Masjosthusmann, S; Reverte, I, 2020)	0.56
"Methylenedioxymethamphetamine (MDMA) and methcathinone (MCAT) are abused psychostimulant drugs that produce adverse effects in human users that include hepatotoxicity and death."	( High ambient temperature increases the toxicity and lethality of 3,4-methylenedioxymethamphetamine and methcathinone. Chen, Y; Hall, FS; Saber, YH; Tran, HTN, 2020)	0.56
" Under the same conditions, even a very high dose of MCAT produced limited toxic or lethal effects."	( High ambient temperature increases the toxicity and lethality of 3,4-methylenedioxymethamphetamine and methcathinone. Chen, Y; Hall, FS; Saber, YH; Tran, HTN, 2020)	0.56
" Although an initial mouse study reported that several cathinones were much less toxic than METH or MDMA, the present results suggest that it will be essential to assess the potential dangers posed by these drugs under high ambient temperatures."	( High ambient temperature increases the toxicity and lethality of 3,4-methylenedioxymethamphetamine and methcathinone. Chen, Y; Hall, FS; Saber, YH; Tran, HTN, 2020)	0.56
"Despite toxicity and unpredictable adverse effects, ecstasy use has increased in the United States."	( Protracted hyperthermia and delayed rhabdomyolysis in ecstasy toxicity: A case report. Eum, KS; Ghaffari-Rafi, A; Jahanmir, J; Villanueva, J, 2020)	0.56
"Clinically, the case highlights how physicians should be aware of the unusual time course adverse effects of ecstasy can have."	( Protracted hyperthermia and delayed rhabdomyolysis in ecstasy toxicity: A case report. Eum, KS; Ghaffari-Rafi, A; Jahanmir, J; Villanueva, J, 2020)	0.56
" No unexpected adverse events were observed."	( First study of safety and tolerability of 3,4-methylenedioxymethamphetamine-assisted psychotherapy in patients with alcohol use disorder. Brew-Girard, E; Burrows, S; Durant, C; Higbed, L; Nutt, DJ; O'Brien, S; Rickard, J; Rose-Morris, A; Sakal, C; Sessa, B; Titheradge, D; Williams, TM; Wilson, S; Wiseman, C, 2021)	0.62
"The recreational use of MDMA (ecstasy) by pregnant women is associated with impaired neuromotor function in infants, but the Adverse Outcome Pathway behind this effect is not clear yet."	( Developmental exposure to MDMA (ecstasy) in zebrafish embryos reproduces the neurotoxicity adverse outcome 'lower motor activity' described in humans. Álvarez, S; Barenys, M; Gómez-Catalán, J; Santamaria, A; Teixidó, E, 2022)	0.72
" Before psychedelics become registered medicines, it is important to know the full range of adverse events (AEs) for making balanced treatment decisions."	( Adverse events in clinical treatments with serotonergic psychedelics and MDMA: A mixed-methods systematic review. Breeksema, JJ; Kamphuis, J; Kuin, BW; Schoevers, RA; van den Brink, W; Vermetten, E, 2022)	0.72

Pharmacokinetics

Excerpt	Reference	Relevance
"The in vivo N-demethylation of (+) and (-)3,4-methylenedioxymethamphetamine (MDMA) to 3,4-methylenedioxyamphetamine (MDA) was determined and the pharmacokinetic relationship between the two compounds calculated."	( Stereochemical differences in the metabolism of 3,4-methylenedioxymethamphetamine in vivo and in vitro: a pharmacokinetic analysis. Chang, AS; Cho, AK; Distefano, EW; Hiramatsu, M; Jenden, DJ, )	0.13
" Cmax values for 125-mg and 75-mg MDMA doses were 236."	( Cardiovascular and neuroendocrine effects and pharmacokinetics of 3, 4-methylenedioxymethamphetamine in humans. Camí, J; de la Torre, R; Farré, M; Mas, M; Ortuño, J; Roset, PN; Segura, J, 1999)	0.3
" Pharmacokinetic drug-drug interactions can occur if MDMA is combined with other recreational or therapeutic drugs that are 2D6 inhibitors."	( Ecstasy: pharmacodynamic and pharmacokinetic interactions. Armstrong, SC; Cozza, KL; Oesterheld, JR, )	0.13
" From a clinical pharmacokinetic perspective, amfetamine-type stimulants are rather homogeneous."	( Clinical pharmacokinetics of amfetamine and related substances: monitoring in conventional and non-conventional matrices. de la Torre, R; Farré, M; Navarro, M; Pacifici, R; Pichini, S; Zuccaro, P, 2004)	0.32
" Following a second dose, plasma concentrations of MDMA increased (AUC 77% and Cmax 29%) in comparison with the first."	( Repeated doses administration of MDMA in humans: pharmacological effects and pharmacokinetics. Camí, J; de la Torre, R; Farré, M; Mathúna, BO; Ortuño, J; Peiró, AM; Pujadas, M; Roset, PN; Torrens, M, 2004)	0.32
" Exposure age differences in the clearance rate and half-life of MDMA were observed, such that the P1-treated animals had a significantly more rapid clearance and a shorter half-life than P11-treated animals did."	( Absorption and clearance of +/-3,4-methylenedioxymethamphetamine from the plasma of neonatal rats. Brown, CA; Skelton, MR; Vinks, AA; Vorhees, CV; Williams, MT, )	0.13
" Here, we examined the pharmacokinetic profile of MDMA in squirrel monkeys after different routes of administration, and explored the relationship between acute plasma MDMA concentrations after repeated oral dosing and subsequent brain serotonin deficits."	( Pharmacokinetic profile of single and repeated oral doses of MDMA in squirrel monkeys: relationship to lasting effects on brain serotonin neurons. Hatzidimitriou, G; Irvine, RJ; McCann, UD; Mechan, A; Ricaurte, GA; Yuan, J, 2006)	0.33
" The purpose of this investigation is to evaluate the pharmacokinetic drug interaction between MDMA and fluoxetine and also to determine the role of P-glycoprotein (P-gp) on mediating drug-drug interactions with MDMA."	( Fluoxetine pretreatment effects pharmacokinetics of 3,4-methylenedioxymethamphetamine (MDMA, ECSTASY) in rat. Eddington, ND; Upreti, VV, 2008)	0.35
" The aim of the study was to evaluate the pharmacodynamic and pharmacokinetic interaction between paroxetine and MDMA in humans."	( Pharmacological interaction between 3,4-methylenedioxymethamphetamine (ecstasy) and paroxetine: pharmacological effects and pharmacokinetics. Abanades, S; de la Torre, R; Farré, M; O'Mathúna, B; Peiró, AM; Roset, PN; Segura, M; Torrens, M, 2007)	0.34
" After the high dose, mean MDMA Cmax significantly increased to 291."	( Plasma pharmacokinetics of 3,4-methylenedioxymethamphetamine after controlled oral administration to young adults. Goodwin, RS; Gorelick, DA; Hayes, RJ; Huestis, MA; Kolbrich, EA; Stein, EA, 2008)	0.35
" At each dose, pharmacokinetic parameters for MDMA and its metabolites 3,4-dihydroxymethamphetamine (HHMA), 4-hydroxy-3-methoxymethamphetamine (HMMA), and 3,4-methylenedioxyamphetamine were determined."	( Nonlinear pharmacokinetics of (+/-)3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") and its major metabolites in squirrel monkeys at plasma concentrations of MDMA that develop after typical psychoactive doses. Maurer, HH; McCann, UD; Mueller, M; Peters, FT; Ricaurte, GA, 2008)	0.35
" The aims of the present studies were to establish discrimination of S(+)-MDMA, R(-)-MDMA, or their combination as racemic MDMA in separate groups of mice to assess cross-substitution tests among all three compounds, to determine the time courses of the training doses, to assess pharmacokinetic variables after single injections and after cumulative dosing, and to define the metabolic dispositions of MDMA enantiomers and their metabolites."	( Discriminative stimulus effects of 3,4-methylenedioxymethamphetamine and its enantiomers in mice: pharmacokinetic considerations. de la Torre, R; Fantegrossi, WE; Mathúna, BO; Murai, N; Pizarro, N, 2009)	0.35
" The aims of the present study were 1) to characterize the pharmacodynamic effects of MDMA on plasma insulin and glucose, 2) to examine the effects of insulin on MDMA-induced thermogenesis and 3) to examine MDMA-induced thermogenesis in an animal model of insulin resistance, the obese Zucker rat."	( Pharmacodynamic characterization of insulin on MDMA-induced thermogenesis. Banks, ML; Buzard, SK; Gehret, CM; Kenaston, MA; Mills, EM; Monroy, AN; Sprague, JE, 2009)	0.35
" A population pharmacokinetic model was developed to describe the changes in MDMA, HMMA, MDA, and HMA concentrations over time and to estimate interanimal variability."	( Population pharmacokinetics of 3,4-methylenedioxymethamphetamine and main metabolites in rats. Debray, M; Declèves, X; Fonsart, J; Hirt, D; Menet, MC; Noble, F; Scherrmann, JM, 2010)	0.36
" The aim of this study was to evaluate the pharmacodynamic effects of interactions caused by concomitants in MDMA tablets on extracellular dopamine and serotonin (5-HT) by microdialysis in the striatum of ethylcarbamate-anesthetized rats."	( Pharmacodynamic interactions between MDMA and concomitants in MDMA tablets on extracellular dopamine and serotonin in the rat brain. Fuchigami, Y; Igari, Y; Ikeda, R; Kuroda, N; Nakashima, K; Wada, M, 2011)	0.37
" blood pressure, heart rate, body temperature) can be reduced, possibly due to a pharmacodynamic interaction at the serotonin reuptake transporter (SERT)."	( Pharmacokinetics and pharmacodynamics of 3,4-methylenedioxymethamphetamine (MDMA): interindividual differences due to polymorphisms and drug-drug interactions. Hondebrink, L; Meulenbelt, J; Rietjens, SJ; Westerink, RH, 2012)	0.38
" We monitored pharmacokinetic and pharmacodynamic variables for drugs and monoamines in the rat brain."	( Warning against co-administration of 3,4-methylenedioxymethamphetamine (MDMA) with methamphetamine from the perspective of pharmacokinetic and pharmacodynamic evaluations in rat brain. Kenichiro, N; Miki, K; Mitsuhiro, W; Naotaka, K; Rie, I; Yuki, F, 2013)	0.39
"The current study aimed to elucidate the role of pharmacokinetic (PK) parameters and neurotransmitter efflux in explaining variability in (±) 3, 4-methylenedioxymethamphetamine (MDMA) self-administration in rats."	( Acquisition of MDMA self-administration: pharmacokinetic factors and MDMA-induced serotonin release. Bird, J; Bradbury, S; Colussi-Mas, J; Mueller, M; Ricaurte, G; Schenk, S, 2014)	0.4
" Pharmacodynamic interactions of methylphenidate and MDMA are likely."	( Pharmacokinetic and pharmacodynamic effects of methylphenidate and MDMA administered alone or in combination. Donzelli, M; Grouzmann, E; Hysek, CM; Liechti, ME; Meyer, N; Schillinger, N; Schmid, Y; Simmler, LD, 2014)	0.4
" MDMA, and the associated pharmacodynamic consequences."	( Nonlinear pharmacokinetics of (+/-)3,4-methylenedioxymethamphetamine (MDMA) and its pharmacodynamic consequences in the rat. Baumann, MH; Concheiro, M; Huestis, MA; Marrone, GF; Rothman, RB; Scheidweiler, KB, 2014)	0.4
" These desirable and adverse effects of MDMA are extensions of its fascinating pharmacologic and pharmacokinetic profile."	( How MDMA's pharmacology and pharmacokinetics drive desired effects and harms. Michael White, C, 2014)	0.4
" Bupropion reduced the Cmax and AUC24 of the CYP2D6-dependently formed metabolite stereoisomers of DHMA 3-sulfate, DHMA 4-sulfate, and 4-hydroxy-3-methoxymethamphetamine (HMMA sulfate and HMMA glucuronide) by approximately 40%."	( Impact of Cytochrome P450 2D6 Function on the Chiral Blood Plasma Pharmacokinetics of 3,4-Methylenedioxymethamphetamine (MDMA) and Its Phase I and II Metabolites in Humans. Kraemer, T; Liechti, ME; Rickli, A; Schmid, Y; Schmidhauser, C; Steuer, AE; Tingelhoff, EH, 2016)	0.43
" Effects of genetic variants in CYP2D6 on the pharmacokinetics and pharmacodynamic effects of MDMA were characterized in 139 healthy individuals (70 men, 69 women) in a pooled analysis of eight double-blind, placebo-controlled crossover studies."	( CYP2D6 function moderates the pharmacokinetics and pharmacodynamics of 3,4-methylene-dioxymethamphetamine in a controlled study in healthy individuals. Hysek, CM; Liechti, ME; Meyer Zu Schwabedissen, HE; Prestin, K; Schmid, Y; Vizeli, P, 2016)	0.43
" A pharmacokinetic curve for the incurred phentermine was successfully produced using the described validated method."	( Hematocrit-Independent Quantitation of Stimulants in Dried Blood Spots: Pipet versus Microfluidic-Based Volumetric Sampling Coupled with Automated Flow-Through Desorption and Online Solid Phase Extraction-LC-MS/MS Bioanalysis. Henion, J; Verplaetse, R, 2016)	0.43
" The principal sources of pharmacodynamic variability are reviewed, with special emphasis on sex-gender, race-ethnicity, genetic differences, interactions, and MDMA acute toxicity, as well as possible therapeutic use."	( Key interindividual determinants in MDMA pharmacodynamics. Farré, M; Muga, R; Papaseit, E; Pérez-Mañá, C; Torrens, M, 2018)	0.48

Compound-Compound Interactions

Excerpt	Reference	Relevance
"Cell-mediated immune response after the administration of MDMA alone and in combination with alcohol was evaluated in a randomized, double-blind, double-dummy, cross-over pilot clinical trial conducted in four healthy MDMA consumers who received single oral doses of 75 mg MDMA (n = 2) or 100 mg MDMA (n = 2), alcohol (0."	( Immunomodulating properties of MDMA alone and in combination with alcohol: a pilot study. de la Torre, R; Di Carlo, S; Farré, M; Ortuño, J; Pacifici, R; Pichini, S; Roset, PN; Segura, J; Zuccaro, P, 1999)	0.3
"Cell-mediated immune response and release of cytokines after the administration of 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy") alone and in combination with ethanol were assessed in a double blind, randomized, crossover, controlled clinical trial."	( Acute effects of 3,4-methylenedioxymethamphetamine alone and in combination with ethanol on the immune system in humans. Di Carlo, S; Farré, M; Hernandez López, C; Ortuño, J; Pacifici, R; Pichini, S; Roset, PN; Segura, J; Torre, RL; Zuccaro, P, 2001)	0.31
"), alone or in combination with exposure to loud music (1 h stimulation), were investigated in Wistar rats."	( Effects on rat sexual behaviour of acute MDMA (ecstasy) alone or in combination with loud music. Bera, I; Bottalico, L; Cagiano, R; Dragulescu, SI; Flace, P; Sabatini, R; Santacroce, L; Vermesan, D; Vermesan, H, )	0.13
" GHB is frequently combined with other recreational drugs although these interactions are not well characterised."	( Sedative and hypothermic effects of gamma-hydroxybutyrate (GHB) in rats alone and in combination with other drugs: assessment using biotelemetry. McGregor, IS; van Nieuwenhuijzen, PS, 2009)	0.35
"Data ascertained in a study of club drug use among 450 gay and bisexual men indicate that at least one class of PDE-5 (phosphodiesterase type 5 inhibitor, sildenafil [Viagra]) is used frequently in combination with club drugs such as methamphetamine, MDMA (3,4 methylenedioxymethamphetamine [ecstasy]), ketamine, cocaine, and GHB (gamma hydroxy butyrate)."	( Sildenafil (Viagra) and club drug use in gay and bisexual men: the role of drug combinations and context. Green, KA; Halkitis, PN, 2007)	0.34
"A method of hollow fiber (HF) liquid phase microextraction (LPME) combined with gas chromatography (GC)-flame ionization detection (FID) was developed for the simultaneous quantification of trace amphetamine (AP), methamphetamine (MA), methylenedioxyamphetamine (MDA), methylenedioxymethamphetamine (MDMA), caffeine and ketamine (KT) in drug abuser urine samples."	( Simultaneous quantification of amphetamines, caffeine and ketamine in urine by hollow fiber liquid phase microextraction combined with gas chromatography-flame ionization detector. Chen, J; He, M; Hu, B; Xiong, J, 2010)	0.36
"5 h); (3) MDMA in combination with alcohol or THC; and (4) placebo."	( Acute effects of MDMA (3,4-methylenedioxymethamphetamine) on EEG oscillations: alone and in combination with ethanol or THC (delta-9-tetrahydrocannabinol). Buitelaar, JK; Dumont, GJ; Lansbergen, MM; van Gerven, JM; Verkes, RJ, 2011)	0.37
" Specifically, suspect and non-target screening, combined with a prioritization approach based on similarity measures between detected features and mass loads of MDMA and amphetamine was implemented."	( Retrospective suspect and non-target screening combined with similarity measures to prioritize MDMA and amphetamine synthesis markers in wastewater. Been, F; Boucheron, T; de Voogt, P; Emke, E; Esseiva, P; Reymond, N; Ter Laak, T, 2022)	0.72
", selective serotonin reuptake inhibitors), so it will be important to understand drug-drug interactions between MDMA or psilocybin and psychiatric medications."	( Drug-drug interactions between psychiatric medications and MDMA or psilocybin: a systematic review. Malcolm, B; Sarparast, A; Stauffer, CS; Thomas, K, 2022)	0.72
" We focus our results on pharmacodynamic, physiological, and subjective outcomes of drug-drug interactions."	( Drug-drug interactions between psychiatric medications and MDMA or psilocybin: a systematic review. Malcolm, B; Sarparast, A; Stauffer, CS; Thomas, K, 2022)	0.72
"As MDMA and psilocybin continue to move through the FDA drug development process, this systematic review offers a compilation of existing research on psychiatric drug-drug interactions with MDMA or psilocybin."	( Drug-drug interactions between psychiatric medications and MDMA or psilocybin: a systematic review. Malcolm, B; Sarparast, A; Stauffer, CS; Thomas, K, 2022)	0.72

Bioavailability

Excerpt	Reference	Relevance
" Significant involution of thymus and spleen confirmed the bioavailability of the corticosterone at both dosages."	( Chronic treatment with supraphysiological levels of corticosterone enhances D-MDMA-induced dopaminergic neurotoxicity in the C57BL/6J female mouse. Johnson, EA; Miller, DB; O'Callaghan, JP, 2002)	0.31
" However, it cannot be excluded that co-administration of Pgp inhibitors such as ritonavir or paroxetine could increase MDMA, MDE and PMA bioavailability and also enhance brain entry leading to severe side effects."	( P-glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine. Haefeli, WE; Ketabi-Kiyanvash, N; Mikus, G; Weiss, J, 2003)	0.32
" Their oral bioavailability is good, with a high distribution volume (4 L/kg) and low binding to plasma proteins (less than 20%)."	( Clinical pharmacokinetics of amfetamine and related substances: monitoring in conventional and non-conventional matrices. de la Torre, R; Farré, M; Navarro, M; Pacifici, R; Pichini, S; Zuccaro, P, 2004)	0.32
" The antidepressant and entactogenic effects induced by an acute dose of MDMA can be accounted for by the notable increase in serotonin bioavailability triggered by the drug."	( [3,4-methylenedioxymethamphetamine ('ecstasy'): its long-term emotional and cognitive effects, and serotonin depletion]. Molero-Chamizo, A, )	0.13
"When tramadol administered intraperitoneally, the absorption rate of this drug was reduced, and a lower Cmax (40%) with longer Tmax (eight-fold) was achieved."	( Evaluation of the Ecstasy influence on tramadol and its main metabolite plasma concentration in rats. Hosseinzadeh Ardakani, Y; Jamali, B; Lavasani, H; Rouini, MR; Sheikholeslami, B, 2017)	0.46

Dosage Studied

Excerpt	Relevance	Reference
" Side effects, insight gained, pleasure, and intensity of the MDMA experience were evaluated as were the influence of set and setting at the time the MDMA was taken and the dosage utilized."	( Phenomenology and sequelae of 3,4-methylenedioxymethamphetamine use. Bravo, GL; Grob, CS; Liester, MB; Walsh, RN, 1992)	0.28
" Three distinct dose-response patterns were observed."	( The effects of MDMA and other methylenedioxy-substituted phenylalkylamines on the structure of rat locomotor activity. Geyer, MA; Paulus, MP, 1992)	0.28
" In the latter assay, both enantiomers of 6 had identical potencies, but their dose-response curves were not parallel."	( Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA). Frescas, SP; Johnson, MP; Nichols, DE; Oberlender, R, 1991)	0.28
" More importantly, if a subacute dosing regimen (every 12 hours for 4 days) was utilized, the combination of S-amphetamine with MDAI resulted in a marked long-term decrease in the levels of cortical, hippocampal and striatal 5-HT, 5-HIAA and the number of 5-HT uptake sites."	( Serotonin neurotoxicity in rats after combined treatment with a dopaminergic agent followed by a nonneurotoxic 3,4-methylenedioxymethamphetamine (MDMA) analogue. Huang, XM; Johnson, MP; Nichols, DE, 1991)	0.28
" MDMA resulted in a monotonic dose-response curve for activity but exhibited a biphasic dose response in ht and hm."	( Application of entropy measures derived from the ergodic theory of dynamical systems to rat locomotor behavior. Geyer, MA; Gold, LH; Mandell, AJ; Paulus, MP, 1990)	0.28
" In rats that had been injected with MDMA on a daily basis either before or after the milk-drinking sessions, the dose-response function of MDMA was shifted to the right, indicating that tolerance had developed."	( Tolerance and cross-tolerance to 3,4-methylenedioxymethamphetamine (MDMA), methamphetamine and methylenedioxyamphetamine. Virus, RM; Woolverton, WL; Zacny, JP, 1990)	0.28
" In order to determine if MDMA produces lasting neurochemical alterations after oral administration, groups of six rats (adult male Sprague-Dawley) were dosed by gavage with either 40 or 80 mg/kg of MDMA or saline vehicle once every 12 hr for 4 days."	( Neurochemical and neurohistological alterations in the rat and monkey produced by orally administered methylenedioxymethamphetamine (MDMA). Ali, SF; Bailey, JR; Frith, CH; Newport, GD; Scallet, AC; Slikker, W, 1988)	0.27
"The possible neurotoxic effects of the alpha-ethyl homologue of MDMA, N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine (MBDB), were examined following a regimen of twice daily dosing for four days."	( Neurotoxic effects of the alpha-ethyl homologue of MDMA following subacute administration. Johnson, MP; Nichols, DE, 1989)	0.28
"0 mg/kg MDA in both components of the multiple schedule, but did not affect the MDMA dose-response curve."	( Behavioral effects of (+-) 3,4-methylenedioxyamphetamine (MDA) and (+-) 3,4-methylenedioxymethamphetamine (MDMA) in the pigeon: interactions with noradrenergic and serotonergic systems. Barrett, JE; Hoffmann, SM; Nader, MA, 1989)	0.28
" Rats were subcutaneously dosed with 40 mg/kg of (+/-) MDMA."	( Stereochemistry of the metabolism of MDMA to MDA. Blanke, RV; Fitzgerald, RL; Glennon, RA; Rosecrans, JA, 1989)	0.28
" Further, they indicate that monkeys are considerably more sensitive than rats to the serotonin-depleting effects of MDMA, and that the dose-response curve of MDMA in the monkey is much steeper than in the rat."	( Studies of MDMA-induced neurotoxicity in nonhuman primates: a basis for evaluating long-term effects in humans. Ricaurte, GA, 1989)	0.28
" Adult female monkeys dosed po with 5 or 10 mg/kg of MDMA twice/day for 4 consecutive days demonstrated no spontaneous behavioral changes or weight loss compared to controls, but forebrain 5-HT concentration was reduced by 80% 1 mon after dosing."	( Behavioral and neurochemical effects of orally administered MDMA in the rodent and nonhuman primate. Ali, SF; Bailey, JR; Holson, RR; Hong, JS; Kolta, MG; McMillan, DE; Paule, MG; Scallet, AC; Scalzo, FM; Slikker, W, 1989)	0.28
" Once trained, these animals were given several doses of drugs used in training and dose-response relationships and ED50 values were generated."	( Discriminative profile of MDMA. Schechter, MD, 1986)	0.27
" Brain sections from rats injected with MDMA according to this dosage regimen were stained by the Fink-Heimer method."	( Biochemical and histological evidence that methylenedioxymethylamphetamine (MDMA) is toxic to neurons in the rat brain. Commins, DL; Schuster, CR; Seiden, LS; Virus, RM; Vosmer, G; Woolverton, WL, 1987)	0.27
" However, the subsequent dose-response experiments indicate that when the fast-trained rats are tested with various doses of MDMA, without prior vehicle treatment, their sensitivity to the drug is less than that of the slowly-trained rats."	( Advantages and disadvantages of a rapid method to train drug discrimination. Schechter, MD, 1988)	0.27
" The current study evaluated the dose-response relationships of MDMA (1."	( Oral administration of 3,4-methylenedioxymethamphetamine (MDMA) produces selective serotonergic depletion in the nonhuman primate. Ali, SF; Bailey, JR; Binienda, Z; Ferguson, SA; Newport, GD; Paule, MG; Scallet, AC; Slikker, W, )	0.13
" First, a dose-response study revealed that all doses of AET tested (5, 10, 20 mg/kg) significantly increased locomotor activity."	( Behavioral characterization of alpha-ethyltryptamine, a tryptamine derivative with MDMA-like properties in rats. Geyer, MA; Krebs, KM, 1993)	0.29
" Nevertheless, the dose-response curve of MMAI is parallel to those of (+)-fenfluramine (m-trifluoromethyl-N-ethylamphetamine) and p-chloroamphetamine."	( Behavioral effects of the highly selective serotonin releasing agent 5-methoxy-6-methyl-2-aminoindan. Marona-Lewicka, D; Nichols, DE, 1994)	0.29
" Two weeks following this dosage regimen, shown to markedly reduce 5-hydroxytryptamine terminals, both glucocorticoid receptor and mineralocorticoid receptor messenger RNA expression were significantly decreased (30-47% fall) in the granule cells of the dentate gyrus and pyramidal cells of CA1-CA4 fields of Ammon's horn, but not in parietal cortex neurons."	( Chronic 3,4-methylenedioxymethamphetamine administration decreases glucocorticoid and mineralocorticoid receptor, but increases 5-hydroxytryptamine1C receptor gene expression in the rat hippocampus. Kelly, PA; Seckl, JR; Sharkey, J; Yau, JL, 1994)	0.29
" Only MDMA and 3,4-(methylenedioxy)amphetamine (MDA) enantiomers were detected at measurable concentrations in the frontal cortices and hippocampis from rats dosed with 10 mg kg-1 of racemic MDMA; in this species the enantiomeric profiles of these two compounds were similar in brain and urine."	( Stereoselective disposition: enantioselective quantitation of 3,4-(methylenedioxy) methamphetamine and three of its metabolites by gas chromatography/electron capture negative ion chemical ionization mass spectrometry. Foltz, RL; Lim, HK; Su, Z, 1993)	0.29
" After an initial acute dose-response assessment, escalating doses of MDMA (0."	( Behavioral and neurochemical effects of chronic methylenedioxymethamphetamine (MDMA) treatment in rhesus monkeys. Ali, SF; Allen, RR; Frederick, DL; Gillam, MP; Paule, MG; Slikker, W, )	0.13
" At each Ta drinking water was freely available following dosing on one session and temporarily unavailable on a second."	( Hyperthermia following MDMA administration in rats: effects of ambient temperature, water consumption, and chronic dosing. Dafters, RI, 1995)	0.29
" The statistical distribution of the drug concentrations compared with the self-reported consumption behaviour of the users may possibly lead to a better understanding of the relationship between drug dosage and corresponding concentrations in hair."	( Concentrations of delta 9-tetrahydrocannabinol, cocaine and 6-monoacetylmorphine in hair of drug abusers. Kauert, G; Röhrich, J, 1996)	0.29
" The effects of a multiple dosing schedule of 5-(glutathion-S-yl)-alpha-MeDA will therefore require investigation before we can define a role for this metabolite in MDA and MDMA mediated neurotoxicity."	( Effects of intracerebroventricular administration of 5-(glutathion-S-yl)-alpha-methyldopamine on brain dopamine, serotonin, and norepinephrine concentrations in male Sprague-Dawley rats. Lau, SS; Miller, RT; Monks, TJ, 1996)	0.29
" The clinical sensitivity and specificity of the overall analysis system (sweat collection and analysis) were 85 and 100%, respectively, using known methamphetamine dosing of volunteers (10, 20, and 25 mg) as the reference standard."	( Detection of methamphetamine in sweat by EIA and GC-MS. Fay, J; Fogerson, R; Niedbala, RS; Schoendorfer, D; Spiehler, V, 1996)	0.29
" To examine the influence of corticosteroids on these changes, adrenalectomized (ADX) rats received the same dosage regimen as above."	( Differential regulation by methylenedioxymethamphetamine of 5-hydroxytryptamine1A receptor density and mRNA expression in rat hippocampus, frontal cortex, and brainstem: the role of corticosteroids. Aguirre, N; Del Río, J; Frechilla, D; García-Osta, A; Lasheras, B, 1997)	0.3
" Analyses by liquid chromatography/mass spectrometry of the larvae and empty puparial cases following base extraction detected the drug in quantities directly related to the dosage of the drug administered to the rabbits serving as a food source."	( Effects of 3,4-methylenedioxymethamphetamine in decomposing tissues on the development of Parasarcophaga ruficornis (Diptera:Sarcophagidae) and detection of the drug in postmortem blood, liver tissue, larvae, and puparia. Goff, ML; Lord, WD; Miller, ML; Omori, AI; Paulson, JD; Richards, E, 1997)	0.3
" A significant hyperactivity of approximately 9 hr duration was observed in the 20 mg/kg and 40 mg/kg groups, whereas there was evidence of a serotonin syndrome in the higher dosage groups."	( An appraisal of the pharmacological and toxicological effects of a single oral administration of 3,4-methylenedioxymethamphetamine (MDMA) in the rat. De Souza, I; Harkin, AJ; Kelly, JP; Leonard, BE, 1997)	0.3
"This study describes the results of a 'side-by-side' comparison of two measurement techniques and two dosing regimens in a discrimination study using rats trained to either 10 mg/kg cocaine or 2 mg/kg 3,4-methylenedioxymethamphetamine (MDMA)."	( Discrete versus cumulative dosing in dose-response discrimination studies. Schechter, MD, 1997)	0.3
" Once all 10 male subjects learned the MDMA-vehicle discrimination at criterion performance level, doses different than the training dose were used to generate a dose-response discrimination gradient."	( MDMA-like stimulus effects of hallucinogens in male Fawn-Hooded rats. Schechter, MD, 1998)	0.3
" Longer-term, larger dosage (acute or cumulative) MDMA consumers were found to be at high risk of developing psychopathological disturbances."	( MDMA ('ecstasy') consumption in the context of polydrug abuse: a report on 150 patients. Bricolo, R; Di Furia, L; Forza, G; Minicuci, N; Schifano, F, 1998)	0.3
" Weekly dosing with MDMA resulted in significantly increased responding at low doses in the paired group but not in the unpaired group."	( Effect of once weekly treatment with 3,4-methylenedioxymethamphetamine on schedule-controlled behavior in rats. Bronson, ME; Nagilla, R; Newland, MC; Snyder, J, 1998)	0.3
" The features of the stimulant-induced seizures were distinct and included the following: (1) the duration of convulsive activity was shortest for cocaine and longest for methamphetamine, (2) only MDMA produced a secondary clonic phase after the initial ictal event, and (3) 4-methylaminorex manifested a very steep dose-response curve."	( Distinct features of seizures induced by cocaine and amphetamine analogs. Hanson, GR; Jensen, M; Johnson, M; White, HS, 1999)	0.3
" In Experiment I, rats were treated with MDMA using several dosing protocols (2."	( (+) 3,4-methylenedioxymethamphetamine ('ecstasy') transiently increases striatal 5-HT1B binding sites without altering 5-HT1B mRNA in rat brain. McEvoy, C; Neumaier, JF; Sexton, TJ, 1999)	0.3
" The decreased rCBF tended to be more pronounced in subjects who received the higher dosage of MDMA."	( Effect of ecstasy [3,4-methylenedioxymethamphetamine (MDMA)] on cerebral blood flow: a co-registered SPECT and MRI study. Chang, L; Ernst, T; Grob, CS; Itti, L; Jose-Melchor, R; Mishkin, FS; Poland, RE, 2000)	0.31
" The possibility that some of these psychological problems are caused by ecstasy-induced neurotoxicity is supported by preclinical evidence of MDMA-induced neurotoxicity and behavioural deficits, evidence of depleted serotonin in heavy ecstasy users, and by dose-response relationships between the extent of exposure to ecstasy and the severity of cognitive impairments."	( Ecstasy (MDMA): a review of its possible persistent psychological effects. Morgan, MJ, 2000)	0.31
" This dosing regimen of MDMA is likely to release DA and to be neurotoxic to 5-HT neurons."	( Pre-exposure to (+/-)3,4-methylenedioxy-methamphetamine (MDMA) facilitates acquisition of intravenous cocaine self-administration in rats. Fletcher, PJ; Robinson, SR; Slippoy, DL, 2001)	0.31
" The pharmacokinetics of MDMA and GHB appear to be nonlinear, making it difficult to estimate a dose-response relationship."	( A comprehensive review of MDMA and GHB: two common club drugs. Guthrie, SK; Teter, CJ, 2001)	0.31
"Establishing functional deficits as a result of neurotoxic dosing regimens of MDMA has been difficult."	( Effects of fenfluramine, m-CPP and triazolam on repeated-acquisition in squirrel monkeys before and after neurotoxic MDMA administration. Delatte, MS; McCann, UD; Moerschbaecher, JM; Ricaurte, GA; Stevenson, MW; Winsauer, PJ; Yuan, J, 2002)	0.31
" Some studies have found a dose-response relationship, so that increasing levels of abuse are associated with greater risk of hemorrhage."	( Cerebrovascular complications of alcohol and sympathomimetic drug abuse. Bruno, A, 2003)	0.32
" The basal firing rate was not modified by either a single dose or repeated doses of MDMA, although the latter produced a shift to the right in the dose-response curve for clonidine-induced inhibition of the firing rate (ED(50) increased by 59%) and a reduction in tyrosine hydroxylase activity (20%) in the hippocampus."	( Short-term effects of 3,4-methylenedioximethamphetamine on noradrenergic activity in locus coeruleus and hippocampus of the rat. Arrue, A; Giralt, MT; Ruiz-Ortega, JA; Ugedo, L, 2003)	0.32
"These results indicate that hyperthermia at the time of dosing with MDMA is not necessary to produce subsequent 5-HT depletion and anxiety in rats."	( Increased anxiety and "depressive" symptoms months after MDMA ("ecstasy") in rats: drug-induced hyperthermia does not predict long-term outcomes. Blokland, A; Clemens, KJ; Cornish, JL; Gurtman, CG; Hunt, GE; Li, KM; McGregor, IS; Morley, KC, 2003)	0.32
" There were 80% reductions in the plasma membrane-associated 5-HT transporters 6 months after either the FEN or MDMA dosing regimen indicating that both treatments produced long-term serotonergic effects."	( Plasma levels of parent compound and metabolites after doses of either d-fenfluramine or d-3,4-methylenedioxymethamphetamine (MDMA) that produce long-term serotonergic alterations. Ali, SF; Bowyer, JF; Frederick, DL; Itzak, Y; Mayorga, AJ; Newport, GD; Paule, MG; Slikker, W; Young, JF, 2003)	0.32
" A small increase in MDMA dosage can lead to a significant rise in drug plasma concentration."	( A bitter pill. Overview of ecstasy (MDMA, MDA) related fatalities. Schifano, F, 2004)	0.32
" Binge dosing produces a higher final peak response than a similar non-divided dose."	( Effect of ambient temperature and a prior neurotoxic dose of 3,4-methylenedioxymethamphetamine (MDMA) on the hyperthermic response of rats to a single or repeated ('binge' ingestion) low dose of MDMA. Colado, MI; Elliott, JM; Green, AR; O'Shea, E; Saadat, KS; Sanchez, V, 2004)	0.32
"Surveys into the pharmacological constituents of ecstasy tablets, dosage levels, and empirical reports of their perceived purity, provide the main data for this review."	( Is ecstasy MDMA? A review of the proportion of ecstasy tablets containing MDMA, their dosage levels, and the changing perceptions of purity. Parrott, AC, 2004)	0.32
" Dosage levels of tablets are also highly variable, with low dose tablet often encountered during the mid-1990s, and high dose tablets now seen more frequently."	( Is ecstasy MDMA? A review of the proportion of ecstasy tablets containing MDMA, their dosage levels, and the changing perceptions of purity. Parrott, AC, 2004)	0.32
" Selectivity may be a consequence of what neurotoxic metabolites are produced (which may depend on dosing schedules), their selectivity for monoamine nerve endings, or the endogenous free radical trapping ability of specific nerve endings, or both."	( Acute and long-term effects of MDMA on cerebral dopamine biochemistry and function. Colado, MI; Green, AR; O'Shea, E, 2004)	0.32
"02 mg/kg) produced a rightward shift in the MDMA dose-response curve."	( Effect of SCH 23390 on (+/-)-3,4-methylenedioxymethamphetamine hyperactivity and self-administration in rats. Brennan, K; Daniela, E; Gittings, D; Hely, L; Schenk, S, 2004)	0.32
" For future research, challenge studies in animals using dosing regimens adapted to human consumption patterns are needed."	( The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA). Freudenmann, RW; Spitzer, M, 2004)	0.32
" To test for a possible dose-response effect, we also performed a median split of 12 moderate MDMA users (22-50 lifetime uses) and 11 heavy users (60-450 uses), and compared these subgroups with non-users."	( Residual neuropsychological effects of illicit 3,4-methylenedioxymethamphetamine (MDMA) in individuals with minimal exposure to other drugs. Barry, S; Halpern, JH; Hudson, JI; Pope, HG; Sherwood, AR; Yurgelun-Todd, D, 2004)	0.32
"The technique of 'binge' dosing (several doses in one session) by recreational users of 3,4-methylenedioxymethamphetamine (MDMA, ecstasy) requires evaluation in terms of its consequences on the acute hyperthermic response and long-term neurotoxicity."	( Effect of repeated ('binge') dosing of MDMA to rats housed at normal and high temperature on neurotoxic damage to cerebral 5-HT and dopamine neurones. Colado, MI; Elliott, JM; Green, AR; O'shea, E; Saadat, KS; Sanchez, V, 2004)	0.32
"This review of chronic tolerance to MDMA (3,4-methylenedioxymetamphetamine) covers the empirical data on dosage escalation, reduced subjective efficacy and bingeing in recreational Ecstasy users."	( Chronic tolerance to recreational MDMA (3,4-methylenedioxymethamphetamine) or Ecstasy. Parrott, AC, 2005)	0.33
" These findings indicate that a dosing regimen of MDMA that depletes brain 5-HT does not alter SERT protein expression or the distribution of SERT between endosomes and the plasma membrane and does not produce detectable evidence for neurotoxicity."	( (+/-)-3,4-Methylenedioxymethamphetamine administration to rats does not decrease levels of the serotonin transporter protein or alter its distribution between endosomes and the plasma membrane. Baumann, MH; Morales, M; Rothman, RB; Wang, X; Xu, H, 2005)	0.33
" The left-shift of the dose-response curve induced by MDMA was greater in normal than in MHS muscle."	( 3,4-Methylenedioxymethamphetamine (ecstasy) activates skeletal muscle nicotinic acetylcholine receptors. Alt, A; Bufler, J; Heffron, JJ; Jurkat-Rott, K; Klingler, W; Lehmann-Horn, F; O'sullivan, G; Schlesinger, F, 2005)	0.33
" Here, we examined the pharmacokinetic profile of MDMA in squirrel monkeys after different routes of administration, and explored the relationship between acute plasma MDMA concentrations after repeated oral dosing and subsequent brain serotonin deficits."	( Pharmacokinetic profile of single and repeated oral doses of MDMA in squirrel monkeys: relationship to lasting effects on brain serotonin neurons. Hatzidimitriou, G; Irvine, RJ; McCann, UD; Mechan, A; Ricaurte, GA; Yuan, J, 2006)	0.33
"3,4-Methylenedioxymethamphetamine (MDMA, designated as "Ecstasy" if illicitly marketed in tablet form) induces significant decrements in neuronal serotonin (5-HT) markers in humans, nonhuman primates, and rats as a function of dosing and dosing regimen."	( MDMA (Ecstasy) and human dopamine, norepinephrine, and serotonin transporters: implications for MDMA-induced neurotoxicity and treatment. Madras, BK; Miller, GM; Verrico, CD, 2007)	0.34
" Reductions in locomotor activity following dosing did not reliably differ from vehicle effects."	( Hyperthermia induced by 3,4-methylenedioxymethamphetamine in unrestrained rhesus monkeys. Crean, RD; Davis, SA; Katner, SN; Lay, CC; Taffe, MA; Von Huben, SN, 2006)	0.33
" Solid dosage formulations were identified using the TICTAC database, chemical tests, and GC-MS screening."	( Analysis for identification in amnesty bin samples from dance venues. Holt, DW; Johnston, A; Kenyon, SL; Lee, T; Ramsey, JD, 2005)	0.33
" Since 3,4-methylenedioxymethamphetamine (MDMA) is known to act as a weak agonist on 5-HT receptors in vertebrates, we tested an exogenous application; however, no significant effect was observed to dosage ranging from 1 nM to 100 microM in larvae with and without an intact CNS."	( Direct influence of serotonin on the larval heart of Drosophila melanogaster. Cooper, RL; Dasari, S, 2006)	0.33
" In this study we assessed the utility of using dose-response properties to distinguish urine samples containing amphetamines from samples containing cross-immunoreactive species."	( Differentiation of amphetamine/methamphetamine and other cross-immunoreactive sympathomimetic amines in urine samples by serial dilution testing. Dietzen, DJ; Koenig, JW; Moyer, TP; Saunders, AN; Turk, J; Woodworth, A, 2006)	0.33
"Use of the slope of the dose-response relationship in patient urine specimens can enhance the PPV of presumptive positive immunoassay results but does not exclude the presence of low amphetamine concentrations in samples containing high concentrations of cross-reactive species."	( Differentiation of amphetamine/methamphetamine and other cross-immunoreactive sympathomimetic amines in urine samples by serial dilution testing. Dietzen, DJ; Koenig, JW; Moyer, TP; Saunders, AN; Turk, J; Woodworth, A, 2006)	0.33
" Important differences between rodent models and human use patterns include frequency of dosing and dosage exposure, routes of administration, tolerance that develops to MDMA after repeated exposure, polydrug use in humans but not by rodents, limits on the repertoire of behaviors that can be exhibited by rodents undergoing IV self-administration procedures, and the question of neurotoxicity as it relates to models of self-administration."	( Relevance of rodent models of intravenous MDMA self-administration to human MDMA consumption patterns. De La Garza, R; Fabrizio, KR; Gupta, A, 2007)	0.34
" In contrast, in the applied single dosage chronic morphine treatment did not influence either the APP and BACE protein levels or the APP mRNA production."	( 3,4-Methylenedioxymethamphetamine (MDMA), but not morphine, alters APP processing in the rat brain. Bjelik, A; Fürst, Z; Gyarmati, Z; Horváth, Z; Hugyecz, M; Janka, Z; Kálmán, J; Pákáski, M; Rakonczay, Z; Tímár, J; Zana, M, 2007)	0.34
" Problematic ecstasy users reported significantly higher levels of ecstasy use, including lifetime consumption, average dosage and binge consumption compared to non-problematic ecstasy users."	( Problematic versus non-problematic ecstasy/MDMA use: the influence of drug usage patterns and pre-existing psychiatric factors. Parrott, AC; Soar, K; Turner, JJ, 2006)	0.33
" The present study examined the impact of self-report methodology on lifetime ecstasy dosage figures using three estimation methods: a single question estimation, a context-based timeline method and a quantity-frequency method."	( Self-reported ecstasy use: the impact of assessment method on dosage estimates in recreational users. Bedi, G; Redman, J, 2006)	0.33
" Mentions on medical death certificates, last year's ecstasy use, number of drug offenders, seizures, prices and dosage levels figures were used for this descriptive and correlational study."	( Ecstasy (MDMA, MDA, MDEA, MBDB) consumption, seizures, related offences, prices, dosage levels and deaths in the UK (1994-2003). Corkery, J; Deluca, P; Ghodse, AH; Oyefeso, A; Schifano, F, 2006)	0.33
" Because findings from the animal literature have indicated that specific dosage regimens of MDMA can produce long-lasting alterations in serotonergic function, existing studies of MDMA effects in humans have examined brain serotonin (5-HT) transporters (5-HTT) and receptors or have examined brain structures or functions potentially affected by MDMA."	( Neuroimaging research in human MDMA users: a review. Cowan, RL, 2007)	0.34
"In recent work we have documented lasting adverse neurochemical and behavioural effects in rats given short-term 'binge' dosing with methylenedioxymethamphetamine (MDMA, Ecstasy), methamphetamine (METH) or their combination."	( Repeated weekly exposure to MDMA, methamphetamine or their combination: long-term behavioural and neurochemical effects in rats. Clemens, KJ; Cornish, JL; Hunt, GE; McGregor, IS, 2007)	0.34
" A more intensive dosing regimen (10 or 20 mg/kg twice daily for 4 days) was used to examine PMA/MDMA effects on cortical 5-HT content."	( Repeated administration of the substituted amphetamine p-methoxyamphetamine produces reductions in cortical 5-HT transporter binding but not 5-HT content, unlike 3,4-methylenedioxyamethamphetamine. Callaghan, PD; Daws, LC; Farrand, K; Hughes, P; Irvine, RJ; Salem, A, 2006)	0.33
" Dose-response relationships were biphasic for MA and (+/-)-MDMA, and asymptotic for (+)-MDMA."	( Estimating the relative reinforcing strength of (+/-)-3,4-methylenedioxymethamphetamine (MDMA) and its isomers in rhesus monkeys: comparison to (+)-methamphetamine. Wang, Z; Woolverton, WL, 2007)	0.34
" The first experiment involved characterisation of the METH dose-response curve for intravenous self-administration."	( Intravenous methamphetamine self-administration in rats: effects of intravenous or intraperitoneal MDMA co-administration. Clemens, KJ; Cornish, JL; Hunt, GE; McGregor, IS, 2006)	0.33
" The effects were seen when the drug was administered twice per day, but the optimal dosing regimen is unknown."	( Developmental effects of +/-3,4-methylenedioxymethamphetamine on spatial versus path integration learning: effects of dose distribution. Schaefer, TL; Vorhees, CV; Williams, MT, 2007)	0.34
" Blood samples for analysis of glucose and lactate were taken at 30-45 min intervals before and after drug dosing and body temperature was monitored by telemetry."	( Serotonin mediates rapid changes of striatal glucose and lactate metabolism after systemic 3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") administration in awake rats. Cumming, P; Gramsbergen, JB, 2007)	0.34
"The purpose of the current study was to establish dose-response relationships for the effects of a number of commonly used illicit stimulants and investigate the behavioral response to increased core temperature."	( Pharmacological and behavioral determinants of cocaine, methamphetamine, 3,4-methylenedioxymethamphetamine, and para-methoxyamphetamine-induced hyperthermia. Irvine, RJ; Jaehne, EJ; Salem, A, 2007)	0.34
" This differed to the slopes of the dose-response curves where MDMA and PMA showed the steepest slope for the doses used followed by methamphetamine then cocaine."	( Pharmacological and behavioral determinants of cocaine, methamphetamine, 3,4-methylenedioxymethamphetamine, and para-methoxyamphetamine-induced hyperthermia. Irvine, RJ; Jaehne, EJ; Salem, A, 2007)	0.34
" Adolescent and adult male rats were injected once daily with saline or with a dose of one of the test drugs for two 5-day dosing periods, separated by a 2-day drug holiday during which they remained in their home cages."	( Age-dependent differences in sensitivity and sensitization to cannabinoids and 'club drugs' in male adolescent and adult rats. Evans, RL; Grainger, DB; Nicholson, KL; Wiley, JL, 2008)	0.35
" Mean MDMA dosage of tablets decreased from 1999 to 2003 and dosage for tablets bearing the same logo appeared to be highly variable."	( Monitoring ecstasy content in France: results from the National Surveillance System 1999-2004. Bello, PY; Giraudon, I, 2007)	0.34
" MDMA irrespective of the dosage produced hyperlocomotion, excessive floor-sniffing and almost absolute suppression of grooming and immobility."	( An analysis of spontaneous behavior following acute MDMA treatment in male and female rats. Bubeníková-Valesová, V; Hlinák, Z; Horácek, J; Pálenícek, T; Votava, M, 2007)	0.34
"The objective of this study was to evaluate the effects of different dosing regimens of MDMA on the ability of mice to learn and recall an active avoidance task."	( MDMA modifies active avoidance learning and recall in mice. Berrendero, F; Cabrero-Castel, A; Maldonado, R; Robledo, P; Trigo, JM, 2008)	0.35
"5-h intervals) 12 h prior to the MDMA dosing regimen (20 mg/kg x 3 at 2-h intervals) aggravated the MDMA-induced dopaminergic toxicity."	( Ketamine pretreatment exacerbated 3,4-methylenedioxymethamphetamine-induced central dopamine toxicity. Cherng, CG; Ho, MC; Ke, JJ; Tsai, CW; Tsai, YP; Yu, L, 2008)	0.35
" Regardless of dosing regimen, MDMA treatment produced path integration deficits as evidenced by an increase in latency to find the goal in the Cincinnati water maze."	( (+/-)-3,4-Methylenedioxymethamphetamine treatment in adult rats impairs path integration learning: a comparison of single vs once per week treatment for 5 weeks. Able, JA; Grace, CE; Gudelsky, GA; Herring, NR; Schaefer, TL; Skelton, MR; Vorhees, CV; Williams, MT, 2008)	0.35
" However, such dosing regimens do not adequately mimic the intermittent use patterns commonly seen in adolescent recreational ecstasy users."	( Development and characterization of a novel animal model of intermittent MDMA ("Ecstasy") exposure during adolescence. Meyer, JS; Piper, BJ; Vancollie, VE, 2008)	0.35
" However, findings on the presence of a dose-response relation are inconsistent, possibly due to individual differences in genetic vulnerability."	( The effect of Ecstasy on memory is moderated by a functional polymorphism in the cathechol-O-methyltransferase (COMT) gene. de Win, MM; den Brink, Wv; Koeter, MW; Schilt, T; Schmand, B; van Amelsvoort, TA; Zinkstok, JR, 2009)	0.35
" In conclusion, we found a group difference in the right SMA and positive dose-response association between lifetime exposure to MDMA and signal magnitude and extent in several brain regions."	( Prior MDMA (Ecstasy) use is associated with increased basal ganglia-thalamocortical circuit activation during motor task performance in humans: an fMRI study. Blackford, JU; Charboneau, EJ; Cowan, RL; Dietrich, MS; Karageorgiou, J; Salomon, RM; Woodward, ND, 2009)	0.35
" The 3 highest MDMA dose groups showed reduced locomotor activity during the first 10 min (of 60 min), especially in the PD 1-5 and 6-10 dosing regimens."	( (+/-)3,4-Methylenedioxymethamphetamine (MDMA) dose-dependently impairs spatial learning in the morris water maze after exposure of rats to different five-day intervals from birth to postnatal day twenty. Grace, CE; Herring, NR; Schaefer, TL; Skelton, MR; Vorhees, CV; Williams, MT, 2009)	0.35
" Finally, given key similarities between MDMA pharmacokinetics in rats and humans, data from rats may be clinically relevant when appropriate dosing conditions are used."	( Effects of dose and route of administration on pharmacokinetics of (+ or -)-3,4-methylenedioxymethamphetamine in the rat. Baumann, MH; Huestis, MA; Kim, I; Rothman, RB; Scheidweiler, KB; Zolkowska, D, 2009)	0.35
"02 mg/kg, subcutaneous), on MDMA self-administration, effects of this dose range on the MA dose-response curve were determined."	( Effect of D1-like and D2-like receptor antagonists on methamphetamine and 3,4-methylenedioxymethamphetamine self-administration in rats. Brennan, KA; Carati, C; Fitzmaurice, PS; Lea, RA; Schenk, S, 2009)	0.35
" Locomotor activity and body weight were assessed during the dosing period and withdrawal-related anxiety was assessed 24 h after drug cessation."	( Residual social, memory and oxytocin-related changes in rats following repeated exposure to γ-hydroxybutyrate (GHB), 3,4-methylenedioxymethamphetamine (MDMA) or their combination. Arnold, JC; Hunt, GE; Long, LE; McGregor, IS; van Nieuwenhuijzen, PS, 2010)	0.36
" In this work, dose-response curves (0."	( Behavioral profiles in rats distinguish among "ecstasy," methamphetamine and 2,5-dimethoxy-4-iodoamphetamine: Mixed effects for "ecstasy" analogues. Cassels, BK; Díaz-Véliz, G; Mora-Gutiérrez, S; Quinteros-Muñoz, D; Rebolledo-Fuentes, M; Sáez-Briones, P, 2010)	0.36
" Both Lifetime Total Ecstasy Consumption (LTEC) and the effect sizes for alcohol, nicotine, amphetamine, cocaine and lysergic acid diethylamide (LSD) were regressed on the mean effect sizes (mES) of the WM subcomponents in order to study dose-response relationships."	( Deterioration of executive functioning in chronic ecstasy users; evidence for multiple drugs effects. Verbaten, MN, 2010)	0.36
"3,4-Methylenedioxymethamphetamine (MDMA) is a racemic drug of abuse and its R- and S-enantiomers are known to differ in their dose-response curve."	( Development and validation of LC-HRMS and GC-NICI-MS methods for stereoselective determination of MDMA and its phase I and II metabolites in human urine. Huestis, MA; Maurer, HH; Meyer, MR; Schwaninger, AE, 2011)	0.37
" THC unexpectedly produced a modest hyperthermic effect when administered alone, but in animals co-treated with both THC and MDMA, there was an attenuation of MDMA-induced hyperthermia on dosing days."	( Chronic administration of THC prevents the behavioral effects of intermittent adolescent MDMA administration and attenuates MDMA-induced hyperthermia and neurotoxicity in rats. Ali, SF; Meyer, JS; Shen, EY, 2011)	0.37
" One thousand two hundred eighty-six expectorated oral fluid specimens collected up to 7 days after dosing were analyzed for MDMA, 3,4-methylenedioxyamphetamine (MDA), 4-hydroxy-3-methoxymethamphetamine (HMMA), and 4-hydroxy-3-methoxyamphetamine (HMA) by gas chromatography mass spectrometry."	( MDMA and metabolite disposition in expectorated oral fluid after controlled oral MDMA administration. Barnes, AJ; Goodwin, RS; Gorelick, DA; Huestis, MA; Kolbrich-Spargo, EA; Scheidweiler, KB, 2011)	0.37
"In this study, mice were exposed to dosing regimens of 3,4-methylenedioxymethamphetamine (MDMA), methamphetamine (METH), or parachloroamphetamine (PCA) known to deplete the monoamine neurotransmitters dopamine and serotonin, and the effects of these dosing regimens on learning and memory were assessed."	( Effects of exposure to amphetamine derivatives on passive avoidance performance and the central levels of monoamines and their metabolites in mice: correlations between behavior and neurochemistry. Fantegrossi, WE; Finton, BJ; Galloway, MP; Howell, LL; Murnane, KS; Perrine, SA, 2012)	0.38
" Whereas ketamine produced progressive increases in activity with repeated administration in rats of both ages, MDMA increased, and then decreased, activity in the chronic dosing regimen in female adolescents only."	( Locomotor activity changes in female adolescent and adult rats during repeated treatment with a cannabinoid or club drug. Evans, RL; Grainger, DB; Nicholson, KL; Wiley, JL, 2011)	0.37
" Therefore acute physiological changes in humans are fairly accurately mimicked in animals by appropriate dosing, although allometric dosing calculations have little value."	( Lost in translation: preclinical studies on 3,4-methylenedioxymethamphetamine provide information on mechanisms of action, but do not allow accurate prediction of adverse events in humans. Fone, KC; Green, AR; King, MV; Shortall, SE, 2012)	0.38
" MDMA exposed infants differed in sex ratio (more male births) and had poorer motor quality and lower milestone attainment at 4 months, with a dose-response relationship to amount of MDMA exposure."	( Neurobehavioral outcomes of infants exposed to MDMA (Ecstasy) and other recreational drugs during pregnancy. Fulton, S; Goodwin, J; Min, MO; Moore, DG; Parrott, AC; Singer, LT; Turner, JJ, )	0.13
" Following a 2-day drug-free period, dose-response curves for hyperactivity produced by MDMA (2."	( Repeated exposure to MDMA and amphetamine: sensitization, cross-sensitization, and response to dopamine D₁- and D₂-like agonists. Bradbury, S; Gittings, D; Schenk, S, 2012)	0.38
" Dopamine, 5-hydroxytryptamine (5-HT) and their major metabolites were measured in striatum, frontal cortex and hippocampus by high performance liquid chromatography 7 days after intermittent dosing and 2h after acute injection."	( Behavioural and neurochemical comparison of chronic intermittent cathinone, mephedrone and MDMA administration to the rat. Ebling, FJ; Fone, KC; Jayson, R; King, MV; Korsah, C; Macerola, AE; Pillidge, KE; Richard Green, A; Shortall, SE; Swaby, RT; Wigmore, PM, 2013)	0.39
" In the present work we studied the in vivo effect of a classic chronic dosing schedule of MDMA in rats, alone or combined with a chronic schedule of NIC, on the density of nAChR and on serotonin reuptake transporters."	( 3,4-Methylenedioxy-methamphetamine induces in vivo regional up-regulation of central nicotinic receptors in rats and potentiates the regulatory effects of nicotine on these receptors. Camarasa, J; Escubedo, E; Garcia-Ratés, S; Pubill, D, 2013)	0.39
" Levels of MDMA and metabolites in plasma were measured in the same animals (n = 3) after dosing on a separate occasion."	( Behavioral effects and pharmacokinetics of (±)-3,4-methylenedioxymethamphetamine (MDMA, Ecstasy) after intragastric administration to baboons. Ator, NA; Goodwin, AK; Mueller, M; Ricaurte, GA; Shell, CD, 2013)	0.39
"Hepatic injury after 3,4-methylenedioxymethamphetamine (MDMA; ecstasy) intoxications is highly unpredictable and does not seem to correlate with either dosage or frequency of use."	( Mixtures of 3,4-methylenedioxymethamphetamine (ecstasy) and its major human metabolites act additively to induce significant toxicity to liver cells when combined at low, non-cytotoxic concentrations. Carmo, H; Carvalho, F; da Silva, DD; Silva, E, 2014)	0.4
" Coupling this intermittent dosing schedule with a novel object recognition task, we found non-spatial memory impaired after only two "weekends" of self-administered MDMA."	( Weekend Ecstasy use disrupts memory in rats. Duvauchelle, CL; McAleer, LM; Schallert, T, 2013)	0.39
" Although many studies have reported that relatively high doses of MDMA deplete serotonin (5-HT) content and decrease the availability of serotonin transporters (5-HTT), limited evidence is available as to the adaptive mechanisms taking place in gene expression levels in the brain following a dosing regimen of MDMA comparable to human consumption."	( 3,4-methylenedioxymethamphetamine induces gene expression changes in rats related to serotonergic and dopaminergic systems, but not to neurotoxicity. Aguirre, N; Cuyas, E; de la Torre, R; Farré, M; Pizarro, N; Puerta, E; Robledo, P, 2014)	0.4
"3,4-Methylenedioxymethamphetamine (MDMA, ecstasy) is a racemic drug of abuse and its two enantiomers are known to differ in their dose-response curves."	( Development and validation of an LC-MS/MS method after chiral derivatization for the simultaneous stereoselective determination of methylenedioxy-methamphetamine (MDMA) and its phase I and II metabolites in human blood plasma. Kraemer, T; Liechti, ME; Schmidhauser, C; Steuer, AE, 2015)	0.42
" This infrequent dosing mitigates adverse event frequency and improves the risk/benefit ratio of MDMA, which may provide a significant advantage over medications that require daily dosing."	( MDMA-assisted therapy: A new treatment model for social anxiety in autistic adults. Danforth, AL; Grob, CS; Struble, CM; Yazar-Klosinski, B, 2016)	0.43
"While hippocampus is a brain region particularly susceptible to the effects of MDMA, the cellular and molecular changes induced by MDMA are still to be fully elucidated, being the dosage regimen, the species and the developmental stage under study great variables."	( Chronic MDMA induces neurochemical changes in the hippocampus of adolescent and young adult rats: Down-regulation of apoptotic markers. García-Cabrerizo, R; García-Fuster, MJ, 2015)	0.42
" The dose-response curve for RU 24969-produced adipsia was also not altered by MDMA self-administration."	( MDMA self-administration fails to alter the behavioral response to 5-HT(1A) and 5-HT(1B) agonists. Aronsen, D; Schenk, S, 2016)	0.43
"Primary outcome measures were (i) the percentage of samples purchased on-line and (ii) the chemical purity of powders (or dosage per tablet); adulteration; and the price per gram, blotter or tablet of drugs bought on-line compared with drugs bought off-line."	( Purity, adulteration and price of drugs bought on-line versus off-line in the Netherlands. Brunt, TM; van der Gouwe, D; van der Pol, P; van Laar, M, 2017)	0.46
" Many studies introduce statistical errors by inconsistently dichotomizing and comparing light and heavy ecstasy users, making dose-response relationships inconclusive."	( The spurious relationship between ecstasy use and neurocognitive deficits: A Bradford Hill review. Amoroso, T, 2019)	0.51
" Current studies focused on the effects of co- and/or postinhibition of VMAT2 on the acute and chronic effects of MDMA and on the dose-response relationship between MDMA-induced elevations in body temperature and subsequent reductions in indolamine concentrations."	( Concurrent Inhibition of Vesicular Monoamine Transporter 2 Does Not Protect Against 3,4-Methylenedioxymethamphetamine (Ecstasy) Induced Neurotoxicity. Cholanians, AB; Lau, SS; Monks, TJ; Phan, AV, 2019)	0.51
" Thus, d2-MDMA functions as a locomotor stimulant similar to MDMA, but, depending on the dosing regimen, may be less susceptible to inducing sensitization to stereotyped movements."	( Locomotor effects of 3,4-methylenedioxymethamphetamine (MDMA) and its deuterated form in mice: psychostimulant effects, stereotypy, and sensitization. Berquist, MD; Fantegrossi, WE; Kristensen, JL; Leth-Petersen, S, 2020)	0.56
" In the current study, adolescent (6-7 weeks of age) and mature adult (16-18 weeks of age) male, Swiss-Webster mice were exposed to MDMA (20 mg/kg) using a binge-like dosing regimen (4 administrations spaced every 2 h)."	( The acute toxic and neurotoxic effects of 3,4-methylenedioxymethamphetamine are more pronounced in adolescent than adult mice. Bagwell, MS; Chitre, NM; Murnane, KS, 2020)	0.56
" He was a chronic user who took his baseline dosage while performing at a music event."	( Protracted hyperthermia and delayed rhabdomyolysis in ecstasy toxicity: A case report. Eum, KS; Ghaffari-Rafi, A; Jahanmir, J; Villanueva, J, 2020)	0.56
", MDPV, αPVP, MCAT, and methylone) with a range of pharmacological effects at dopamine and serotonin transporters were compared to cocaine and MDMA using dose-response analysis under a simple FR schedule and behavioral economic procedures that generated demand curves for two doses of each drug."	( Reinforcing effects of synthetic cathinones in rhesus monkeys: Dose-response and behavioral economic analyses. Bergman, J; de Moura, FB; Kohut, SJ; Paronis, CA; Prisinzano, TE; Sherwood, A, 2021)	0.62
" Both Sch 23390 and haloperidol attenuated the discrimination of low MDPV doses and essentially shifted the dose-response curve to the right but failed to block discrimination of the training dose."	( Characterization of 3,4-methylenedioxypyrovalerone discrimination in female Sprague-Dawley rats. Baker, LE; Cargile, KJ; Lunn, JA; Thomas, AM, 2021)	0.62
" The dosing of MDMA is used to allow the therapist to probe the underlying trauma without causing emotional distress."	( MDMA-Assisted Psychotherapy for Treatment of Posttraumatic Stress Disorder: A Systematic Review With Meta-Analysis. Hernandez, AV; Sicignano, DJ; Smith, KW; White, CM, 2022)	0.72
" Controlled study data on dosing using well-characterized pharmaceutical formulations of the substances are scarce."	( Dosing Psychedelics and MDMA. Holze, F; Liechti, ME, 2022)	0.72
"We discuss how processes of change may extend beyond the MDMA dosing sessions themselves."	( Potential processes of change in MDMA-Assisted therapy for social anxiety disorder: Enhanced memory reconsolidation, self-transcendence, and therapeutic relationships. Kati Lear, M; Luoma, JB; Pilecki, B; Shahar, B; Wagner, A, 2022)	0.72
"35 mg in a piperazine mix, while the highest dosed tablet contained 237."	( 3,4-Methylenedioxymethamphetamine quantification via benchtop Abbate, V; Araneda, JF; Frascione, N; Frinculescu, A; Maier, AFG; Ramsey, J; Riegel, SD; Shine, T, 2022)	0.72
" Following the training, dose substitution was used to generate full dose-response curves for METH and the three synthetic cathinones."	( Relative reinforcing effects of dibutylone, ethylone, and N-ethylpentylone: self-administration and behavioral economics analysis in rats. Du, H; Fu, D; Lai, M; Liu, H; Wang, Y; Xu, P; Xu, Z; Zhou, W, 2022)	0.72
"Dibutylone, ethylone, and N-ethylpentylone functioned as reinforcers, and the inverted U-shaped dose-response curves were obtained."	( Relative reinforcing effects of dibutylone, ethylone, and N-ethylpentylone: self-administration and behavioral economics analysis in rats. Du, H; Fu, D; Lai, M; Liu, H; Wang, Y; Xu, P; Xu, Z; Zhou, W, 2022)	0.72
"Locomotor activity and conditioned place preference dose-response curves were generated at 20±2°C for two amphetamine analogues (MDMA and methamphetamine [METH]) and two cathinone analogues (MDPV and α-pyrrolidinopentiophenone [αPVP]) in mice."	( Effects of ambient temperature on locomotor activity and place conditioning elicited by abused psychostimulants in mice: Role of 3,4-methylenedioxy moiety. Fantegrossi, WE; Fitzgerald, LR; Gannon, BM; Godwin, CO; Hughes-Meredith, HD; Rice, KC, 2023)	0.91

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Role	Description
neurotoxin	A poison that interferes with the functions of the nervous system.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
amphetamines	Amines that constitute a class of central nervous system stimulants based on the structure of the parent amphetamine 1-phenylpropan-2-amine.
benzodioxoles
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Cytochrome P450 2D6	Homo sapiens (human)	Ki	12.9000	0.0001	1.1986	8.0000	AID589099
Aldo-keto reductase family 1 member B1	Bos taurus (cattle)	Ki	0.0007	0.0004	0.0018	0.0044	AID408801
Sodium-dependent noradrenaline transporter	Homo sapiens (human)	IC50 (µMol)	0.9351	0.0008	1.5416	20.0000	AID471667; AID488693; AID752492
Sodium-dependent noradrenaline transporter	Homo sapiens (human)	Ki	0.3980	0.0003	1.4656	10.0000	AID752492
Sodium-dependent serotonin transporter	Homo sapiens (human)	IC50 (µMol)	1.1761	0.0001	0.8645	8.7096	AID471666; AID488692; AID576813; AID752491
Sodium-dependent serotonin transporter	Homo sapiens (human)	Ki	0.3169	0.0000	0.7048	8.1930	AID408801; AID408802; AID752491
Sodium-dependent serotonin transporter	Rattus norvegicus (Norway rat)	IC50 (µMol)	1.0600	0.0003	0.8197	8.4900	AID471630
Sodium-dependent dopamine transporter	Homo sapiens (human)	IC50 (µMol)	1.7609	0.0007	1.8419	46.0000	AID471668; AID488694; AID752493
Sodium-dependent dopamine transporter	Homo sapiens (human)	Ki	0.8970	0.0002	1.1115	8.0280	AID752493
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Sodium-dependent noradrenaline transporter	Homo sapiens (human)	EC50 (µMol)	1.0000	0.0820	31.0243	168.9080	AID1240857
Sodium-dependent dopamine transporter	Rattus norvegicus (Norway rat)	EC50 (µMol)	0.2780	0.0007	0.1791	1.4500	AID1442370
Sodium-dependent serotonin transporter	Homo sapiens (human)	EC50 (µMol)	174.3795	0.0011	2.3883	8.7000	AID1240855; AID471635; AID471638
Sodium-dependent serotonin transporter	Rattus norvegicus (Norway rat)	EC50 (µMol)	0.0720	0.0007	0.4236	1.7650	AID1442369
Sodium-dependent dopamine transporter	Homo sapiens (human)	EC50 (µMol)	1.0000	0.0125	0.7668	1.7000	AID1240856
Trace amine-associated receptor 1	Rattus norvegicus (Norway rat)	EC50 (µMol)	1.7000	0.0139	0.4263	2.0440	AID635290
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Cytochrome P450 2D6	Homo sapiens (human)	Km	9.8500	1.1000	3.7286	8.2000	AID254565; AID256544; AID256545; AID256546
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
xenobiotic metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
cholesterol metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
estrogen metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
coumarin metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
alkaloid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
alkaloid catabolic process	Cytochrome P450 2D6	Homo sapiens (human)
monoterpenoid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
isoquinoline alkaloid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 2D6	Homo sapiens (human)
retinol metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Cytochrome P450 2D6	Homo sapiens (human)
negative regulation of binding	Cytochrome P450 2D6	Homo sapiens (human)
oxidative demethylation	Cytochrome P450 2D6	Homo sapiens (human)
negative regulation of cellular organofluorine metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
arachidonic acid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
retinoid metabolic process	Aldo-keto reductase family 1 member B1	Bos taurus (cattle)
prostaglandin metabolic process	Aldo-keto reductase family 1 member B1	Bos taurus (cattle)
retinol metabolic process	Aldo-keto reductase family 1 member B1	Bos taurus (cattle)
monoamine transport	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
neurotransmitter transport	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
chemical synaptic transmission	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
response to xenobiotic stimulus	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
response to pain	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
norepinephrine uptake	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
neuron cellular homeostasis	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
amino acid transport	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
norepinephrine transport	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
dopamine uptake involved in synaptic transmission	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
sodium ion transmembrane transport	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
monoamine transport	Sodium-dependent serotonin transporter	Homo sapiens (human)
response to hypoxia	Sodium-dependent serotonin transporter	Homo sapiens (human)
neurotransmitter transport	Sodium-dependent serotonin transporter	Homo sapiens (human)
response to nutrient	Sodium-dependent serotonin transporter	Homo sapiens (human)
memory	Sodium-dependent serotonin transporter	Homo sapiens (human)
circadian rhythm	Sodium-dependent serotonin transporter	Homo sapiens (human)
response to xenobiotic stimulus	Sodium-dependent serotonin transporter	Homo sapiens (human)
response to toxic substance	Sodium-dependent serotonin transporter	Homo sapiens (human)
positive regulation of gene expression	Sodium-dependent serotonin transporter	Homo sapiens (human)
positive regulation of serotonin secretion	Sodium-dependent serotonin transporter	Homo sapiens (human)
negative regulation of cerebellar granule cell precursor proliferation	Sodium-dependent serotonin transporter	Homo sapiens (human)
negative regulation of synaptic transmission, dopaminergic	Sodium-dependent serotonin transporter	Homo sapiens (human)
response to estradiol	Sodium-dependent serotonin transporter	Homo sapiens (human)
social behavior	Sodium-dependent serotonin transporter	Homo sapiens (human)
vasoconstriction	Sodium-dependent serotonin transporter	Homo sapiens (human)
sperm ejaculation	Sodium-dependent serotonin transporter	Homo sapiens (human)
negative regulation of neuron differentiation	Sodium-dependent serotonin transporter	Homo sapiens (human)
positive regulation of cell cycle	Sodium-dependent serotonin transporter	Homo sapiens (human)
negative regulation of organ growth	Sodium-dependent serotonin transporter	Homo sapiens (human)
behavioral response to cocaine	Sodium-dependent serotonin transporter	Homo sapiens (human)
enteric nervous system development	Sodium-dependent serotonin transporter	Homo sapiens (human)
brain morphogenesis	Sodium-dependent serotonin transporter	Homo sapiens (human)
serotonin uptake	Sodium-dependent serotonin transporter	Homo sapiens (human)
membrane depolarization	Sodium-dependent serotonin transporter	Homo sapiens (human)
platelet aggregation	Sodium-dependent serotonin transporter	Homo sapiens (human)
cellular response to retinoic acid	Sodium-dependent serotonin transporter	Homo sapiens (human)
cellular response to cGMP	Sodium-dependent serotonin transporter	Homo sapiens (human)
regulation of thalamus size	Sodium-dependent serotonin transporter	Homo sapiens (human)
conditioned place preference	Sodium-dependent serotonin transporter	Homo sapiens (human)
sodium ion transmembrane transport	Sodium-dependent serotonin transporter	Homo sapiens (human)
amino acid transport	Sodium-dependent serotonin transporter	Homo sapiens (human)
monoamine transport	Sodium-dependent dopamine transporter	Homo sapiens (human)
neurotransmitter transport	Sodium-dependent dopamine transporter	Homo sapiens (human)
lactation	Sodium-dependent dopamine transporter	Homo sapiens (human)
sensory perception of smell	Sodium-dependent dopamine transporter	Homo sapiens (human)
locomotory behavior	Sodium-dependent dopamine transporter	Homo sapiens (human)
response to xenobiotic stimulus	Sodium-dependent dopamine transporter	Homo sapiens (human)
response to iron ion	Sodium-dependent dopamine transporter	Homo sapiens (human)
dopamine transport	Sodium-dependent dopamine transporter	Homo sapiens (human)
adenohypophysis development	Sodium-dependent dopamine transporter	Homo sapiens (human)
response to nicotine	Sodium-dependent dopamine transporter	Homo sapiens (human)
positive regulation of multicellular organism growth	Sodium-dependent dopamine transporter	Homo sapiens (human)
regulation of dopamine metabolic process	Sodium-dependent dopamine transporter	Homo sapiens (human)
response to cocaine	Sodium-dependent dopamine transporter	Homo sapiens (human)
dopamine biosynthetic process	Sodium-dependent dopamine transporter	Homo sapiens (human)
dopamine catabolic process	Sodium-dependent dopamine transporter	Homo sapiens (human)
response to ethanol	Sodium-dependent dopamine transporter	Homo sapiens (human)
cognition	Sodium-dependent dopamine transporter	Homo sapiens (human)
dopamine uptake involved in synaptic transmission	Sodium-dependent dopamine transporter	Homo sapiens (human)
response to cAMP	Sodium-dependent dopamine transporter	Homo sapiens (human)
norepinephrine uptake	Sodium-dependent dopamine transporter	Homo sapiens (human)
prepulse inhibition	Sodium-dependent dopamine transporter	Homo sapiens (human)
dopamine uptake	Sodium-dependent dopamine transporter	Homo sapiens (human)
hyaloid vascular plexus regression	Sodium-dependent dopamine transporter	Homo sapiens (human)
amino acid transport	Sodium-dependent dopamine transporter	Homo sapiens (human)
norepinephrine transport	Sodium-dependent dopamine transporter	Homo sapiens (human)
sodium ion transmembrane transport	Sodium-dependent dopamine transporter	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
monooxygenase activity	Cytochrome P450 2D6	Homo sapiens (human)
iron ion binding	Cytochrome P450 2D6	Homo sapiens (human)
oxidoreductase activity	Cytochrome P450 2D6	Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen	Cytochrome P450 2D6	Homo sapiens (human)
heme binding	Cytochrome P450 2D6	Homo sapiens (human)
anandamide 8,9 epoxidase activity	Cytochrome P450 2D6	Homo sapiens (human)
anandamide 11,12 epoxidase activity	Cytochrome P450 2D6	Homo sapiens (human)
anandamide 14,15 epoxidase activity	Cytochrome P450 2D6	Homo sapiens (human)
retinal dehydrogenase activity	Aldo-keto reductase family 1 member B1	Bos taurus (cattle)
prostaglandin H2 endoperoxidase reductase activity	Aldo-keto reductase family 1 member B1	Bos taurus (cattle)
allyl-alcohol dehydrogenase activity	Aldo-keto reductase family 1 member B1	Bos taurus (cattle)
glycerol dehydrogenase [NADP+] activity	Aldo-keto reductase family 1 member B1	Bos taurus (cattle)
all-trans-retinol dehydrogenase (NADP+) activity	Aldo-keto reductase family 1 member B1	Bos taurus (cattle)
actin binding	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
neurotransmitter transmembrane transporter activity	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
neurotransmitter:sodium symporter activity	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
dopamine:sodium symporter activity	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
norepinephrine:sodium symporter activity	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
protein binding	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
monoamine transmembrane transporter activity	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
alpha-tubulin binding	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
metal ion binding	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
beta-tubulin binding	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
integrin binding	Sodium-dependent serotonin transporter	Homo sapiens (human)
monoatomic cation channel activity	Sodium-dependent serotonin transporter	Homo sapiens (human)
neurotransmitter transmembrane transporter activity	Sodium-dependent serotonin transporter	Homo sapiens (human)
serotonin:sodium:chloride symporter activity	Sodium-dependent serotonin transporter	Homo sapiens (human)
protein binding	Sodium-dependent serotonin transporter	Homo sapiens (human)
monoamine transmembrane transporter activity	Sodium-dependent serotonin transporter	Homo sapiens (human)
antiporter activity	Sodium-dependent serotonin transporter	Homo sapiens (human)
syntaxin-1 binding	Sodium-dependent serotonin transporter	Homo sapiens (human)
cocaine binding	Sodium-dependent serotonin transporter	Homo sapiens (human)
sodium ion binding	Sodium-dependent serotonin transporter	Homo sapiens (human)
identical protein binding	Sodium-dependent serotonin transporter	Homo sapiens (human)
nitric-oxide synthase binding	Sodium-dependent serotonin transporter	Homo sapiens (human)
actin filament binding	Sodium-dependent serotonin transporter	Homo sapiens (human)
serotonin binding	Sodium-dependent serotonin transporter	Homo sapiens (human)
protease binding	Sodium-dependent dopamine transporter	Homo sapiens (human)
signaling receptor binding	Sodium-dependent dopamine transporter	Homo sapiens (human)
neurotransmitter transmembrane transporter activity	Sodium-dependent dopamine transporter	Homo sapiens (human)
dopamine:sodium symporter activity	Sodium-dependent dopamine transporter	Homo sapiens (human)
protein binding	Sodium-dependent dopamine transporter	Homo sapiens (human)
monoamine transmembrane transporter activity	Sodium-dependent dopamine transporter	Homo sapiens (human)
dopamine binding	Sodium-dependent dopamine transporter	Homo sapiens (human)
amine binding	Sodium-dependent dopamine transporter	Homo sapiens (human)
protein-containing complex binding	Sodium-dependent dopamine transporter	Homo sapiens (human)
metal ion binding	Sodium-dependent dopamine transporter	Homo sapiens (human)
protein phosphatase 2A binding	Sodium-dependent dopamine transporter	Homo sapiens (human)
heterocyclic compound binding	Sodium-dependent dopamine transporter	Homo sapiens (human)
norepinephrine:sodium symporter activity	Sodium-dependent dopamine transporter	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
mitochondrion	Cytochrome P450 2D6	Homo sapiens (human)
endoplasmic reticulum	Cytochrome P450 2D6	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 2D6	Homo sapiens (human)
cytoplasm	Cytochrome P450 2D6	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 2D6	Homo sapiens (human)
plasma membrane	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
cell surface	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
membrane	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
neuronal cell body membrane	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
presynaptic membrane	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
plasma membrane	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
axon	Sodium-dependent noradrenaline transporter	Homo sapiens (human)
plasma membrane	Sodium-dependent serotonin transporter	Homo sapiens (human)
focal adhesion	Sodium-dependent serotonin transporter	Homo sapiens (human)
endosome membrane	Sodium-dependent serotonin transporter	Homo sapiens (human)
endomembrane system	Sodium-dependent serotonin transporter	Homo sapiens (human)
presynaptic membrane	Sodium-dependent serotonin transporter	Homo sapiens (human)
membrane raft	Sodium-dependent serotonin transporter	Homo sapiens (human)
synapse	Sodium-dependent serotonin transporter	Homo sapiens (human)
postsynaptic membrane	Sodium-dependent serotonin transporter	Homo sapiens (human)
serotonergic synapse	Sodium-dependent serotonin transporter	Homo sapiens (human)
synapse	Sodium-dependent serotonin transporter	Homo sapiens (human)
plasma membrane	Sodium-dependent serotonin transporter	Homo sapiens (human)
neuron projection	Sodium-dependent serotonin transporter	Homo sapiens (human)
cytoplasm	Sodium-dependent dopamine transporter	Homo sapiens (human)
plasma membrane	Sodium-dependent dopamine transporter	Homo sapiens (human)
cell surface	Sodium-dependent dopamine transporter	Homo sapiens (human)
membrane	Sodium-dependent dopamine transporter	Homo sapiens (human)
axon	Sodium-dependent dopamine transporter	Homo sapiens (human)
neuron projection	Sodium-dependent dopamine transporter	Homo sapiens (human)
neuronal cell body	Sodium-dependent dopamine transporter	Homo sapiens (human)
axon terminus	Sodium-dependent dopamine transporter	Homo sapiens (human)
membrane raft	Sodium-dependent dopamine transporter	Homo sapiens (human)
postsynaptic membrane	Sodium-dependent dopamine transporter	Homo sapiens (human)
dopaminergic synapse	Sodium-dependent dopamine transporter	Homo sapiens (human)
flotillin complex	Sodium-dependent dopamine transporter	Homo sapiens (human)
axon	Sodium-dependent dopamine transporter	Homo sapiens (human)
presynaptic membrane	Sodium-dependent dopamine transporter	Homo sapiens (human)
plasma membrane	Sodium-dependent dopamine transporter	Homo sapiens (human)
neuronal cell body membrane	Sodium-dependent dopamine transporter	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID752493	Inhibition of [3H]dopamine uptake at human DAT expressed in HEK293 cells preincubated for 10 mins prior to substrate addition measured after 4 mins by FLIPR assay	2013	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11	An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'.
AID1143929	Displacement of [3H]epibatidine from alpha4beta2 nAChR in Sprague-Dawley rat brain cortical membrane after 3 hrs by liquid scintillation spectrometric analysis	2014	European journal of medicinal chemistry, Jun-23, Volume: 81	Molecular basis of the selective binding of MDMA enantiomers to the alpha4beta2 nicotinic receptor subtype: synthesis, pharmacological evaluation and mechanistic studies.
AID184518	Monoamine levels in rat brain were evaluated after subcutaneous administration of 40 mg/kg for HVA	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID184514	Monoamine levels in rat brain were evaluated after subcutaneous administration of 40 mg/kg for 5-HIAA	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID256552	Vmax for oxidation to MDA by cytochrome P450 2D6 (Phe120Ala mutant)	2005	Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19	Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID752492	Inhibition of [3H]norepinephrine uptake at human NET expressed in HEK293 cells preincubated for 10 mins prior to substrate addition measured after 4 mins by FLIPR assay	2013	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11	An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'.
AID1240850	Binding affinity to SERT in Sprague-Dawley rat brain synaptosomes assessed as induction of [3H]5-HT release by liquid scintillation counting method relative to control	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine.
AID51043	Binding affinity was determined towards serotonin uptake site in presence of [3H]paroxetine radioligand in rat hippocampal homogenate	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID589099	Mechanism based inhibition of human cytochrome P450 2D6 measured by dextromethorphan O-demethylation using recombinant CYP2D6	2005	Current drug metabolism, Oct, Volume: 6, Issue:5	Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.
AID255155	Vmax for oxidation to 3,4-OH-MA by cytochrome P450 2D6 (wild type pSP19T7LT); expressed in 10E5 fluorescence units min-1 nmol-1 CYP	2005	Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19	Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID471630	Inhibition of [3H]5-HT reuptake at rat SERT expressed in HEK293 cells after 2 mins by liquid scintillation counting	2009	European journal of medicinal chemistry, Dec, Volume: 44, Issue:12	Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents.
AID1240855	Binding affinity to human SERT expressed in HEK293 cells assessed as induction of [3H]5-HT release by liquid scintillation counting method	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine.
AID184521	Monoamine levels in rat hippocampus were evaluated after subcutaneous administration of 40 mg/kg for 5-HT	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID254565	Michaelis-Menten constant for oxidation to 3,4-OH-MA by cytochrome P450 2D6 (wild type pSP19T7LT)	2005	Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19	Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID1240847	Binding affinity to SERT in Sprague-Dawley rat brain synaptosomes assessed as induction of [3H]5-HT release by liquid scintillation counting method	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine.
AID488695	Cytotoxicity against human HEK293 cells assessed as cell viability after 48 hrs by neutral red assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted alpha-alkylthioamphetamines.
AID184520	Monoamine levels in rat hippocampus were evaluated after subcutaneous administration of 40 mg/kg for 5-HIAA	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID471638	Induction of human SERT-dependent cytotoxicity in SERT expressing human DG75 cells after 48 hrs by neutral red assay	2009	European journal of medicinal chemistry, Dec, Volume: 44, Issue:12	Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents.
AID752491	Inhibition of [3H]5-HT uptake at human SERT expressed in HEK293 cells preincubated for 10 mins prior to substrate addition measured after 4 mins by FLIPR assay	2013	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11	An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'.
AID589098	Mechanism based inhibition of human cytochrome P450 2D6 measured by dextromethorphan O-demethylation using human liver microsomes	2005	Current drug metabolism, Oct, Volume: 6, Issue:5	Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.
AID471668	Inhibition of human dopamine transporter	2009	European journal of medicinal chemistry, Dec, Volume: 44, Issue:12	Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents.
AID184517	Monoamine levels in rat brain were evaluated after subcutaneous administration of 40 mg/kg for DOPAC	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID175195	Percentage of animals disrupted was determined in groups of MDMA trained rats at a dose of 3.81 (umol/kg),(no of animals = 8)	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID471639	Cytotoxicity against human SH-SY5Y cells after 48 hrs by neutral red assay	2009	European journal of medicinal chemistry, Dec, Volume: 44, Issue:12	Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents.
AID488696	Cytotoxicity against human HEK293 cells over expressing human SERT assessed as cell viability after 48 hrs by neutral red assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted alpha-alkylthioamphetamines.
AID51041	Compounds were evaluated for binding of [3H]paroxetine to rat brain cortical homogenate and number of binding sites (Bmax) for serotonin	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID88606	Compounds were evaluated for binding of [3H]paroxetine to rat hippocampal homogenate and number of binding sites (Bmax) for serotonin	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID576812	Cytotoxicity against human HEK293 cells expressing human SERT assessed as decrease in cell viability after 48 hrs neutral red dye assay	2011	Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3	Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents.
AID256544	Michaelis-Menten constant for oxidation to MDA by cytochrome P450 2D6 (Phe120Ala mutant)	2005	Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19	Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID1143930	Displacement of [3H]epibatidine from alpha4beta2 nAChR in Sprague-Dawley rat brain cortical membrane after 3 hrs	2014	European journal of medicinal chemistry, Jun-23, Volume: 81	Molecular basis of the selective binding of MDMA enantiomers to the alpha4beta2 nicotinic receptor subtype: synthesis, pharmacological evaluation and mechanistic studies.
AID576805	Cytotoxicity against human chemoresistant DG75 cells expressing SERT assessed as decrease in cell viability 10 or 50 uM after 72 hrs Alamar blue assay	2011	Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3	Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents.
AID178743	Effective dose was evaluated for drug discrimination in I-trained rats	1991	Journal of medicinal chemistry, May, Volume: 34, Issue:5	Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA).
AID191394	Compound was tested for hallucinogenic activity in rats at the dose 0.34 (mg/kg); Number of rats selecting the LSD lever/ number of rats responding (2/8)	1986	Journal of medicinal chemistry, Oct, Volume: 29, Issue:10	Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.
AID184516	Monoamine levels in rat brain were evaluated after subcutaneous administration of 40 mg/kg for DA	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID488698	Cytotoxicity against human HEK293 cells over expressing human DAT assessed as cell viability after 48 hrs by neutral red assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted alpha-alkylthioamphetamines.
AID471666	Inhibition of [3H]5-HT uptake at SERT	2009	European journal of medicinal chemistry, Dec, Volume: 44, Issue:12	Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents.
AID1240848	Binding affinity to DAT in Sprague-Dawley rat brain synaptosomes assessed as induction of [3H]MPP+ release by liquid scintillation counting method	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine.
AID1143932	Stimulation of [3H]epibatidine binding to alpha4beta2 nAChR in rat PC12 cells at 100 uM preincubated for 24 hrs followed by radioligand addition measured after 90 mins by liquid scintillation spectrometric analysis	2014	European journal of medicinal chemistry, Jun-23, Volume: 81	Molecular basis of the selective binding of MDMA enantiomers to the alpha4beta2 nicotinic receptor subtype: synthesis, pharmacological evaluation and mechanistic studies.
AID1240852	Binding affinity to NET in Sprague-Dawley rat brain synaptosomes assessed as induction of [3H]MPP+ release by liquid scintillation counting method relative to control	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine.
AID190258	Tested for stimulus generation in rats trained to discriminate MDMA from saline at a dose 7.62 (umol/kg),(number of animals = 8)	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID488692	Binding affinity to human SERT	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted alpha-alkylthioamphetamines.
AID184519	Monoamine levels in rat brain were evaluated after subcutaneous administration of 40 mg/kg for NE	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID488694	Binding affinity to human DAT	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted alpha-alkylthioamphetamines.
AID175196	Percentage of animals disrupted was determined in groups of MDMA trained rats at a dose of 7.62 (umol/kg),(no of animals = 8)	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID1240857	Binding affinity to human NET expressed in HEK293 cells assessed as induction of [3H]MPP+ release by liquid scintillation counting method	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine.
AID1442373	Induction of stimulus generalization in rat trained to discriminate PMMA assessed as appropriate responding level to training drug by two lever method	2017	Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7	The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.
AID51042	Binding affinity was determined towards serotonin uptake site in presence of [3H]paroxetine radioligand in rat brain cortical homogenate	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID1143928	In vivo stimulation of [3H]epibatidine binding to nicotinic acetylcholine receptor in rat prefrontal cortex relative to control	2014	European journal of medicinal chemistry, Jun-23, Volume: 81	Molecular basis of the selective binding of MDMA enantiomers to the alpha4beta2 nicotinic receptor subtype: synthesis, pharmacological evaluation and mechanistic studies.
AID471634	Cytotoxicity against human HEK293 cells after 48 hrs by neutral red assay	2009	European journal of medicinal chemistry, Dec, Volume: 44, Issue:12	Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents.
AID408802	Displacement of [3H]paroxetine from human SERT expressed in HEK293 cells	2008	Bioorganic & medicinal chemistry, Jun-15, Volume: 16, Issue:12	Carbon-11 labeled indolylpropylamine analog as a new potential PET agent for imaging of the serotonin transporter.
AID635290	Activation of rat TAAR1 expressed in HEK293 cells assessed as accumulation of [3H]cAMP after 1 hr by competitive binding assay	2011	Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23	Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class.
AID576803	Cytotoxicity against human SH-SY5Y cells expressing human SERT assessed as decrease in cell viability after 48 hrs neutral red dye assay	2011	Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3	Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents.
AID471635	Induction of human SERT-dependent cytotoxicity in SERT expressing HEK293 cells after 48 hrs by neutral red assay	2009	European journal of medicinal chemistry, Dec, Volume: 44, Issue:12	Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents.
AID184513	Monoamine levels in at hippocampus were evaluated after subcutaneous administration of 40 mg/kg for NE	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID576813	Inhibition of [3H]-serotonin reuptake at human SERT expressed in HEK293 cells after 15 to 20 mins by fluorescence neurotransmitter transporter assay	2011	Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3	Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents.
AID1442370	Activity at DAT in rat synaptosomes assessed as release of [3H]DA after 5 mins by liquid scintillation counting method	2017	Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7	The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.
AID191210	Compound was tested for hallucinogenic activity in rats at 1.38 dose(mg/kg); Number of rats selecting the LSD lever/ number of rats responding (2/8)	1986	Journal of medicinal chemistry, Oct, Volume: 29, Issue:10	Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.
AID1442369	Activity at SERT in rat synaptosomes assessed as release of [3H]HT after 5 mins by liquid scintillation counting method	2017	Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7	The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.
AID576811	Cytotoxicity against human HEK293 cells assessed as decrease in cell viability after 48 hrs neutral red dye assay	2011	Bioorganic & medicinal chemistry, Feb-01, Volume: 19, Issue:3	Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents.
AID176238	Inhibitory activity was determined MDMA trained rats	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID1240856	Binding affinity to human DAT expressed in HEK293 cells assessed as induction of [3H]MPP+ release by liquid scintillation counting method	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine.
AID1240849	Binding affinity to NET in Sprague-Dawley rat brain synaptosomes assessed as induction of [3H]MPP+ release by liquid scintillation counting method	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine.
AID184515	Monoamine levels in rat brain were evaluated after subcutaneous administration of 40 mg/kg for 5-HT	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID190256	Tested for stimulus generation in rats trained to discriminate MDMA from saline at a dose 1.90 (umol/kg) (number of animals = 8)	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID1442371	Activity at NET in rat synaptosomes assessed as release of [3H]NE after 30 mins by liquid scintillation counting method	2017	Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7	The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.
AID175194	Percentage of animals disrupted was determined in groups of MDMA trained rats at a dose of 1.90 (umol/kg),(no of animals = 8)	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID256554	Vmax for oxidation to N-OH-MDMA by cytochrome P450 2D6 (Phe120Ala mutant); expressed in 10E5 fluorescence units min-1 nmol-1 CYP	2005	Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19	Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID175193	Percentage of animals disrupted was determined in groups of MDMA trained rats at a dose of 0.95 (umol/kg),(no of animals = 8)	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
AID191223	Compound was tested for hallucinogenic activity in rats at 1.84 dose(mg/kg); Number of rats selecting the LSD lever/ number of rats responding (3/8)	1986	Journal of medicinal chemistry, Oct, Volume: 29, Issue:10	Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.
AID191400	Compound was tested for hallucinogenic activity in rats at the dose 0.69(mg/kg); Number of rats selecting the LSD lever/ number of rats responding (0/8)	1986	Journal of medicinal chemistry, Oct, Volume: 29, Issue:10	Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.
AID256546	Michaelis-Menten constant for oxidation to N-OH-MDMA by cytochrome P450 2D6 (Phe120Ala mutant)	2005	Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19	Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID488693	Binding affinity to human NET	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted alpha-alkylthioamphetamines.
AID256553	Vmax for oxidation to 3,4-OH-MA by cytochrome P450 2D6 (Phe120Ala mutant); expressed in 10E5 fluorescence units min-1 nmol-1 CYP	2005	Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19	Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID471667	Inhibition of human noradrenaline transporter	2009	European journal of medicinal chemistry, Dec, Volume: 44, Issue:12	Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents.
AID256545	Michaelis-Menten constant for oxidation to 3,4-OH-MA by cytochrome P450 2D6 (Phe120Ala mutant)	2005	Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19	Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID191232	Compound was tested for hallucinogenic activity in rats at 2.19 dose(mg/kg); 0/1, highest dose tested	1986	Journal of medicinal chemistry, Oct, Volume: 29, Issue:10	Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.
AID488697	Cytotoxicity against human HEK293 cells over expressing human NET assessed as cell viability after 48 hrs by neutral red assay	2010	Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11	Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted alpha-alkylthioamphetamines.
AID1240851	Binding affinity to DAT in Sprague-Dawley rat brain synaptosomes assessed as induction of [3H]MPP+ release by liquid scintillation counting method relative to control	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine.
AID408801	Displacement of [3H]citalopram from human SERT expressed in HEK293 cells	2008	Bioorganic & medicinal chemistry, Jun-15, Volume: 16, Issue:12	Carbon-11 labeled indolylpropylamine analog as a new potential PET agent for imaging of the serotonin transporter.
AID190257	Tested for stimulus generation in rats trained to discriminate MDMA from saline at a dose 3.81 (umol/kg),(number of animals = 8)	1990	Journal of medicinal chemistry, Feb, Volume: 33, Issue:2	Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	125 (3.11)	18.7374
1990's	618 (15.39)	18.2507
2000's	1698 (42.29)	29.6817
2010's	1221 (30.41)	24.3611
2020's	353 (8.79)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	211 (4.93%)	5.53%
Reviews	469 (10.97%)	6.00%
Case Studies	454 (10.62%)	4.05%
Observational	8 (0.19%)	0.25%
Other	3,134 (73.29%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (62)

Trial Overview

Trial	Phase	Enrollment	Study Type	Start Date	Status
Neurobiology and Pharmacokinetics of Acute MDMA Administration [NCT01148342]	Phase 1	187 participants (Actual)	Interventional	2004-02-10	Completed
An Open-Label, Multi-Site Phase 2 Study of the Safety and Effect of Manualized MDMA-Assisted Psychotherapy for the Treatment of Severe Posttraumatic Stress Disorder (Canada) [NCT03485287]	Phase 2	4 participants (Actual)	Interventional	2018-03-13	Completed
An Open-Label, Multi-Site Phase 2 Study of the Safety and Effect of Manualized MDMA-Assisted Therapy for the Treatment of Severe Posttraumatic Stress Disorder [NCT03282123]	Phase 2	38 participants (Actual)	Interventional	2017-11-16	Completed
A Placebo-controlled, Randomized, Blinded, Dose Finding Phase 2 Pilot Safety Study of MDMA-assisted Therapy for Social Anxiety in Autistic Adults [NCT02008396]	Phase 2	12 participants (Actual)	Interventional	2014-04-11	Completed
Effect of MDMA (Serotonin Release) on Fear Extinction [NCT03527316]	Early Phase 1	30 participants (Actual)	Interventional	2019-10-18	Completed
Phase II Dose-response Pilot Study of 3,4-methylenedioxymethamphetamine (MDMA)-Assisted Psychotherapy in Subjects With Anxiety Associated With Advanced-stage Cancer. [NCT00252174]	Phase 2	2 participants (Actual)	Interventional	2007-02-28	Terminated(stopped due to Lack of funds and insufficient patient population for study enrollment.)
Effect of Stimulant Drugs on Social Perception [NCT03790618]	Phase 1	40 participants (Anticipated)	Interventional	2016-06-01	Recruiting
MDMA-assisted Therapy for Adjustment Disorder (AD) in Dyads of Patients With Cancer and a Concerned Significant Other [NCT05584826]	Phase 2	20 participants (Anticipated)	Interventional	2022-10-06	Recruiting
Abuse Liability and Human Pharmacology of Mephedrone (4-methylmethcathinone,4-MMC) [NCT02232789]	Phase 1	12 participants (Actual)	Interventional	2014-09-30	Completed
The Effects of MDMA on Prefrontal and Amygdala Activation in Posttraumatic Stress Disorder [NCT03752918]	Phase 1	20 participants (Anticipated)	Interventional	2024-01-31	Not yet recruiting
Acute Effects of R- and S-MDMA in Healthy Subjects [NCT05277636]	Phase 1	24 participants (Anticipated)	Interventional	2022-10-01	Recruiting
Does Serotonin System Stimulation Increase Pro-social Behavior? - A Comparative Pharmacological Neuroscientific Study in Healthy Humans [NCT06081179]	Phase 1	120 participants (Anticipated)	Interventional	2023-10-24	Recruiting
Pharmacological Interaction Between Clonidine and 3,4-methylenedioxymethamphetamine (MDMA, Ecstasy) [NCT01136278]	Phase 1	16 participants (Actual)	Interventional	2010-07-31	Completed
Acute Effects of 3,4-methylenedioxymethamphetamine (MDMA) With and Without a Booster Dose (MDMA-booster Study) [NCT05809271]	Phase 1	24 participants (Anticipated)	Interventional	2023-11-17	Recruiting
Phase II Pilot Randomized Double-Blind Placebo-Controlled Study of 3,4-methylenedioxymethamphetamine (MDMA)Assisted Psychotherapy in Posttraumatic Stress Disorder (PTSD)- Switzerland [NCT00353938]	Phase 2	14 participants (Actual)	Interventional	2006-09-13	Completed
Acute Effects of 2C-B Compared With MDMA and Psilocybin in Healthy Subjects [NCT05523401]	Phase 1	24 participants (Anticipated)	Interventional	2023-06-30	Not yet recruiting
An Open-Label Feasibility and Safety Study of MDMA-Assisted Group Therapy for the Treatment of Posttraumatic Stress Disorder in Veterans [NCT05961527]	Phase 1/Phase 2	18 participants (Anticipated)	Interventional	2023-10-01	Recruiting
A Randomized, Double-Blind, Single-Site Phase II 2-Arm Study to Compare the Safety and Preliminary Efficacy of Manualized MDMA-Assisted Therapy to Low Dose D-Amphetamine Assisted Therapy in Veterans For The Treatment of Moderate to Severe PTSD [NCT05790239]	Phase 2	40 participants (Anticipated)	Interventional	2023-10-31	Not yet recruiting
A Randomized, Double-Blind, Placebo-Controlled, Multi-Site Phase 3 Study of the Efficacy and Safety of Manualized MDMA-Assisted Psychotherapy for the Treatment of Severe Posttraumatic Stress Disorder [NCT03537014]	Phase 3	100 participants (Actual)	Interventional	2018-11-21	Completed
Pharmacological Interaction Between Duloxetine and 3,4-Methylenedioxymethamphetamine (MDMA, Ecstasy): Pharmacodynamics (PD) and Pharmacokinetics (PK) [NCT00990067]	Phase 1	16 participants (Actual)	Interventional	2009-11-30	Completed
Open-label Phase 2 Study of MDMA-Assisted Psychotherapy in Veterans With Combat-Related, Refractory PTSD [NCT04264026]	Phase 2	10 participants (Anticipated)	Interventional	2021-07-29	Recruiting
Social Anxiety MDMA-Assisted Therapy Investigation (SAMATI): A Randomized, Delayed Treatment Control Phase 2 Study of the Safety and Effectiveness of Manualized MDMA-Assisted Therapy for the Treatment of Social Anxiety Disorder [NCT05138068]	Phase 2	90 participants (Actual)	Interventional	2022-04-13	Active, not recruiting
Interactive Effects of Doxazosin and 3,4-Methylenedioxymethamphetamine (MDMA) in Healthy Subjects [NCT01386177]	Phase 1	16 participants (Actual)	Interventional	2011-07-31	Completed
The Effects of MDMA on Sleep Architecture, Water Homeostasis and Cognitive Function [NCT01053403]		12 participants (Actual)	Interventional	2010-04-30	Completed
An Intermediate-size Multi-site Expanded Access Program for MDMA-assisted Psychotherapy for Patients With Treatment-resistant PTSD [NCT04438512]		0 participants	Expanded Access		No longer available
An Open-Label Feasibility and Safety Study of MDMA-Assisted Group Therapy for the Treatment of Posttraumatic Stress Disorder in Veterans [NCT05173831]	Phase 2	0 participants (Actual)	Interventional	2023-09-30	Withdrawn(stopped due to Transfer of Sponsorship)
A Phase 2, Open Label Study of the Safety and Effectiveness of MDMA-assisted Therapy for Participants With Posttraumatic Stress Disorder [NCT04968938]	Phase 2	0 participants (Actual)	Interventional	2022-08-31	Withdrawn(stopped due to Sponsor decided not to pursue the study. Study ended prior to study start.)
A Randomized Trial to Compare MDMA-assisted Therapy (MDMA-AT) Versus Cognitive Processing Therapy (CPT), a VA Standard-of-care Psychotherapy for PTSD, for the Treatment of Severe Posttraumatic Stress Disorder [NCT05837845]	Phase 2	30 participants (Anticipated)	Interventional	2024-02-29	Not yet recruiting
A Randomized Trial of MDMA-Assisted Cognitive-Behavioural Conjoint Therapy (CBCT) Versus CBCT in Dyads in Which One Member Has Posttraumatic Stress Disorder (PTSD) [NCT06044675]	Phase 2	60 participants (Anticipated)	Interventional	2023-10-15	Not yet recruiting
A Phase 2, Open-Label, Randomized Comparative Effectiveness Study for MDMA-Assisted Psychotherapy in U.S. Veterans With Chronic PTSD [NCT04784143]	Phase 2	60 participants (Anticipated)	Interventional	2021-11-08	Recruiting
Open-Label Proof of Concept Feasibility Study to Explore the Safety, Tolerability and Potential Role of MDMA-Assisted Psychotherapy for the Treatment of Detoxified Patients With Alcohol Use Disorder [NCT04158778]	Phase 1	20 participants (Anticipated)	Interventional	2018-04-18	Active, not recruiting
Circulating Oxytocin Changes in Response to the Oxytocin System Stimulator MDMA in Patients With Diabetes Insipidus and Healthy Controls [NCT04648137]		30 participants (Actual)	Interventional	2021-02-05	Completed
A Phase 1, Single Center, Open Label, Randomized Sequence, 2-period Cross-over Study to Determine the Effect of Food on the Relative Bioavailability of 3,4-methylenedioxymethamphetamine (MDMA) Oral Formulation in Healthy Volunteers [NCT05147402]	Phase 1	14 participants (Actual)	Interventional	2022-07-28	Completed
A Multi-Site Open-Label Safety Extension Study of Manualized MDMA-Assisted Psychotherapy for the Treatment of Participants With Posttraumatic Stress Disorder [NCT04714359]	Phase 3	85 participants (Actual)	Interventional	2021-03-08	Completed
An Open-Label, Multi-Site Phase 2 Study of the Safety and Feasibility of MDMA-Assisted Psychotherapy for Eating Disorders [NCT04454684]	Phase 2	36 participants (Anticipated)	Interventional	2023-12-31	Not yet recruiting
A Phase 1, Open-Label, Multi-Site Study to Assess Psychological Effects of MDMA-Assisted Psychotherapy When Administered to Healthy Volunteers [NCT04073433]	Phase 1	150 participants (Anticipated)	Interventional	2023-12-31	Not yet recruiting
A Phase I, Open Label, Study of 3,4-Methylenedioxymethamphetamine (MDMA) Tolerability and Pharmacokinetics in Subjects With Moderate Hepatic Impairment Compared to Matched Control Subjects With Normal Hepatic Function [NCT03606538]	Phase 1	16 participants (Anticipated)	Interventional	2024-03-29	Not yet recruiting
Evaluation of 3,4-methylenedioxymethamphetamine (MDMA) on Startle Response [NCT03181763]	Phase 1	34 participants (Actual)	Interventional	2017-03-14	Completed
Exploring Mechanisms of Action of ±3,4-methylenedioxymethamphetamine (MDMA)- Assisted Psychotherapy for Posttraumatic Stress Disorder (PTSD) [NCT02102802]		10 participants (Actual)	Observational	2014-01-31	Completed
A Phase 1 Placebo-Controlled, Double-Blind Crossover Study to Assess Psychological Effects of MDMA When Administered to Healthy Volunteers [NCT01404754]	Phase 1	107 participants (Actual)	Interventional	2011-04-09	Completed
Tolerability of MDMA in Schizophrenia [NCT05770375]	Phase 1/Phase 2	20 participants (Anticipated)	Interventional	2023-09-01	Not yet recruiting
An Open-Label, Phase 2, Multicenter Feasibility Study of Manualized MDMA-Assisted Psychotherapy With an Optional fMRI Sub-Study Assessing Changes in Brain Activity in Subjects With Posttraumatic Stress Disorder [NCT04030169]	Phase 2	40 participants (Anticipated)	Interventional	2020-06-24	Enrolling by invitation
A Randomized, Double-Blind, Placebo-Controlled, Multi-Site Phase 3 Study of the Efficacy and Safety of Manualized MDMA-Assisted Psychotherapy for the Treatment of Posttraumatic Stress Disorder of Moderate or Greater Severity [NCT04077437]	Phase 3	121 participants (Actual)	Interventional	2020-09-02	Completed
A Pilot Study of MDMA-Assisted Massed Exposure Therapy for PTSD (MDMA PE) [NCT05746572]	Phase 4	40 participants (Anticipated)	Interventional	2024-01-31	Recruiting
A Randomized, Double-Blind, Placebo-Controlled Phase 2 Pilot Study of MDMA-Assisted Psychotherapy for Anxiety Associated With a Life-Threatening Illness [NCT02427568]	Phase 2	18 participants (Actual)	Interventional	2015-05-14	Completed
A Randomized, Double-Blind, Dose Response Phase 2 Pilot Study of Manualized MDMA-Assisted Psychotherapy in Subjects With Chronic, Treatment-Resistant Posttraumatic Stress Disorder (PTSD) [NCT01793610]	Phase 2	29 participants (Actual)	Interventional	2013-05-13	Completed
A Randomized, Double-Blind, Active Placebo-Controlled Phase 2 Pilot Study of MDMA-assisted Psychotherapy in People With Chronic, Treatment-Resistant Posttraumatic Stress Disorder (PTSD) [NCT01689740]	Phase 2	10 participants (Actual)	Interventional	2013-01-17	Completed
Randomized, Triple-Blind, Phase 2 Pilot Study Comparing 3 Different Doses of MDMA in Conjunction With Manualized Therapy in 24 Veterans, Firefighters and Police Officers With Chronic Posttraumatic Stress Disorder (PTSD) [NCT01211405]	Phase 2	26 participants (Actual)	Interventional	2010-11-10	Completed
MDMA-assisted Therapy in Twelve People With War and Terrorism-related Posttraumatic Stress Disorder (PTSD) [NCT00402298]	Phase 2	5 participants (Actual)	Interventional	2007-05-27	Terminated(stopped due to This study was terminated after enrolling five subjects due to staff turnover and its effects on quality of data collection.)
Emotional Effects of Methylphenidate and MDMA in Healthy Subjects [NCT01465685]	Phase 1	16 participants (Actual)	Interventional	2011-12-31	Completed
Phase II Clinical Trial Testing the Safety and Efficacy of 3,4-Methylenedioxymethamphetamine (MDMA)-Assisted Psychotherapy in Subjects With Chronic Posttraumatic Stress Disorder [NCT00090064]	Phase 2	23 participants (Actual)	Interventional	2004-03-12	Completed
Influence of Bupropion on the Effects of MDMA [NCT01771874]	Phase 1	16 participants (Actual)	Interventional	2013-01-31	Completed
Abuse Potential and Human Pharmacology of Methylone [NCT05488171]	Phase 1	17 participants (Actual)	Interventional	2021-12-01	Active, not recruiting
Effects of MDMA (Ecstasy) and Methylphenidate (Ritalin) on Social Cognition [NCT01616407]	Early Phase 1	30 participants (Actual)	Interventional	2012-08-31	Completed
Preliminary Effectiveness of Individual and Group MDMA-assisted Therapy for Israeli Veterans With PTSD and Moral Injury From Special Forces Undercover Units [NCT05732155]	Phase 2	60 participants (Anticipated)	Interventional	2023-06-01	Not yet recruiting
Effects of MDMA-like Substances in Healthy Subjects [NCT04847206]	Phase 1	24 participants (Anticipated)	Interventional	2021-12-01	Recruiting
"Effects of Carvedilol on the Cardiovascular and Subjective Response to MDMA (3,4-Methylenedioxymethamphetamine, Ecstasy)" [NCT01270672]		16 participants (Actual)	Interventional	2011-01-31	Completed
Role of Dopamine, Serotonin and 5-HT2A Receptors in Emotion Processing [NCT03019822]	Early Phase 1	28 participants (Actual)	Interventional	2017-02-01	Completed
An Open-Label Proof-of-Principle Study Testing the Use of an Additional MDMA-Assisted Therapy Session in People Who Relapsed After Participating in a Phase 2 Clinical Trial of MDMA-Assisted Therapy to Treat Chronic, Treatment-Resistant Posttraumatic Stres [NCT01458327]	Phase 2	3 participants (Actual)	Interventional	2010-12-15	Completed
MDMA-assisted Massed Prolonged Exposure for PTSD [NCT06117306]	Phase 3	10 participants (Anticipated)	Interventional	2024-01-02	Not yet recruiting
Effects of MDMA Co-administration on the Response to LSD in Healthy Subjects [NCT04516902]	Phase 1	24 participants (Actual)	Interventional	2021-01-01	Completed
A Randomized, Double-Blind, Controlled Phase 2 Pilot Study of Manualized 3,4-methylenedioxymethamphetamine (MDMA)-Assisted Psychotherapy in 12 Subjects With Treatment-Resistant Posttraumatic Stress Disorder (PTSD) - Canada [NCT01958593]	Phase 2	6 participants (Actual)	Interventional	2014-10-14	Terminated(stopped due to This pilot study was terminated early by sponsor due to insufficient rate of accrual.)
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

Trial	Outcome
NCT00090064 (2) [back to overview]	Change in Impact of Events Scale Revised (IES-R) From Baseline to 2-month Follow-up
NCT00090064 (2) [back to overview]	Change in Clinician-Administered PTSD Scale (CAPS-IV) From Baseline to 2-month Follow-up
NCT00353938 (2) [back to overview]	Change From Baseline to Primary Endpoint in Clinician Administered PTSD Scale for DSM-IV (CAPS-IV)
NCT00353938 (2) [back to overview]	Change From Baseline to Primary Endpoint in Posttraumatic Stress Diagnostic Scale (PDS)
NCT00402298 (3) [back to overview]	Change in Clinician-Administered PTSD Scale for DSM-IV (CAPS-IV) at 2-month Follow-up
NCT00402298 (3) [back to overview]	Change in Clinician-Administered PTSD Scale for DSM-IV (CAPS-IV) at 12-month Follow-up
NCT00402298 (3) [back to overview]	Change in Clinician-Administered PTSD Scale for DSM-IV (CAPS-IV) at 6-month Follow-up
NCT01211405 (9) [back to overview]	Change in Neuroticism-Extroversion-Openness Personality Inventory-Revised (NEO-PI-R) From Baseline to Primary Endpoint
NCT01211405 (9) [back to overview]	Stage 1 Primary Endpoint Clinician-Administered PTSD Scale (CAPS-IV) Total Score
NCT01211405 (9) [back to overview]	Change in Posttraumatic Growth Inventory (PTGI) From Baseline to Primary Endpoint
NCT01211405 (9) [back to overview]	Change in Pittsburgh Sleep Quality Index (PSQI) From Baseline to Primary Endpoint
NCT01211405 (9) [back to overview]	Change in Global Assessment of Function (GAF) From Baseline to Primary Endpoint
NCT01211405 (9) [back to overview]	Change in Dissociative Experience Scale (DES-II) From Baseline to Primary Endpoint
NCT01211405 (9) [back to overview]	Change in Clinician-Administered PTSD Scale (CAPS-IV) From Baseline to Primary Endpoint
NCT01211405 (9) [back to overview]	Change in Beck Depression Inventory (BDI-II) From Baseline to Primary Endpoint
NCT01211405 (9) [back to overview]	Baseline Clinician-Administered PTSD Scale (CAPS-IV) Total Score
NCT01458327 (5) [back to overview]	Change in Clinician-Administered PTSD Scale (CAPS-IV) From Baseline to 2-month Follow-up
NCT01458327 (5) [back to overview]	Clinician-Administered PTSD Scale (CAPS-IV)) at 12-month Follow-up
NCT01458327 (5) [back to overview]	Clinician-Administered PTSD Scale for DSM-IV (CAPS-IV) at 2-month Follow-up
NCT01458327 (5) [back to overview]	Baseline Clinician-Administered PTSD Scale for DSM-IV (CAPS-IV)
NCT01458327 (5) [back to overview]	Change in Clinician-Administered PTSD Scale (CAPS-IV) From Baseline to 12-month Follow-up
NCT01689740 (15) [back to overview]	Change in Posttraumatic Stress Diagnostic Scale (PDS) Symptom Severity Score From End of Stage 1 to End of Stage 2
NCT01689740 (15) [back to overview]	Change in Posttraumatic Stress Diagnostic Scale (PDS) Symptom Severity Score From Baseline to Long-Term Follow-Up
NCT01689740 (15) [back to overview]	Change in Clinical Administered PTSD Scale (CAPS-IV) Total Score From Baseline to Long-Term Follow-Up
NCT01689740 (15) [back to overview]	Change in Clinical Administered PTSD Scale (CAPS-IV) Total Score From Baseline to End of Stage 1
NCT01689740 (15) [back to overview]	Change in Beck Depression Inventory (BDI-II) Total Scores From Baseline to Long-Term Follow-Up
NCT01689740 (15) [back to overview]	Change in Beck Depression Inventory (BDI-II) Total Scores From Baseline to End of Stage 1
NCT01689740 (15) [back to overview]	Change in Global Assessment of Functioning (GAF) Scale From Baseline to Long-Term Follow-Up
NCT01689740 (15) [back to overview]	Change in Beck Depression Inventory (BDI-II) Total Score From End of Stage 1 to End of Stage 2
NCT01689740 (15) [back to overview]	Change in Pittsburgh Sleep Quality Index (PSQI) From End of Stage 1 to End of Stage 2
NCT01689740 (15) [back to overview]	Change in Posttraumatic Stress Diagnostic Scale (PDS) Symptom Severity Score From Baseline to End of Stage 1
NCT01689740 (15) [back to overview]	Change in Pittsburgh Sleep Quality Index (PSQI) From Baseline to End of Stage 1
NCT01689740 (15) [back to overview]	Change in Global Assessment of Functioning (GAF) Scale From End of Stage 1 to End of Stage 2
NCT01689740 (15) [back to overview]	Change in Global Assessment of Functioning (GAF) Scale From Baseline to End of Stage 1
NCT01689740 (15) [back to overview]	Change in Clinical Administered PTSD Scale (CAPS-IV) Total Score From End of Stage 1 to End of Stage 2
NCT01689740 (15) [back to overview]	Change in Pittsburgh Sleep Quality Index (PSQI) From Baseline to Long-Term Follow-Up
NCT01793610 (7) [back to overview]	Beck Depression Inventory II (BDI-II) at Baseline (ITT)
NCT01793610 (7) [back to overview]	Beck Depression Inventory II (BDI-II) at One Month Post 2nd Experimental Session (ITT)
NCT01793610 (7) [back to overview]	Change in Beck Depression Inventory II (BDI-II) From Baseline to One Month Post 2nd Experimental Session (ITT)
NCT01793610 (7) [back to overview]	Change in Clinician Administered PTSD Scale for DSM-IV (CAPS-IV) Total Severity Score From Baseline to One Month Post 2nd Experimental Session (ITT)
NCT01793610 (7) [back to overview]	Change in Pittsburgh Sleep Quality Index (PSQI) From Baseline to One Month Post 2nd Experimental Session (ITT)
NCT01793610 (7) [back to overview]	Clinician Administered PTSD Scale for DSM-IV (CAPS-IV) Total Severity Score at Baseline (ITT)
NCT01793610 (7) [back to overview]	Clinician Administered PTSD Scale for DSM-IV (CAPS-IV) Total Severity Score at One Month Post 2nd Experimental Session (ITT)
NCT01958593 (1) [back to overview]	Change in Clinician-Administered PTSD Scale (CAPS-IV) Score From Baseline to Primary Endpoint
NCT02008396 (3) [back to overview]	Liebowitz Social Anxiety Scale (LSAS) Total Score at Baseline
NCT02008396 (3) [back to overview]	Liebowitz Social Anxiety Scale (LSAS) Total Score 1-Month Post Experimental Session 2
NCT02008396 (3) [back to overview]	Change in Leibowitz Social Anxiety Scale (LSAS) Total Score From Baseline to 1-Month Post Experimental Session 2
NCT02427568 (12) [back to overview]	Change in Death Attitudes Profile (DAP) From Baseline to Primary Endpoint
NCT02427568 (12) [back to overview]	Change in MADRS Score From Baseline to Primary Endpoint
NCT02427568 (12) [back to overview]	Change in Global Assessment of Functioning (GAF) Score From Baseline to Primary Endpoint
NCT02427568 (12) [back to overview]	Change in Beck Depression Inventory-II (BDI-II) Score From Baseline to Primary Endpoint
NCT02427568 (12) [back to overview]	Baseline STAI Trait Score
NCT02427568 (12) [back to overview]	Change in Functional Assessment of Chronic Illness Therapy Scale (FACIT) From Baseline to Primary Endpoint
NCT02427568 (12) [back to overview]	Primary Endpoint STAI Trait Score
NCT02427568 (12) [back to overview]	Change in State Trait Anxiety Inventory (STAI) Trait Score From Baseline to Primary Endpoint
NCT02427568 (12) [back to overview]	Change in STAI State Score From Baseline to Primary Endpoint
NCT02427568 (12) [back to overview]	Change in Self-Compassion Scale (SCS) From Baseline to Primary Endpoint
NCT02427568 (12) [back to overview]	Change in Posttraumatic Growth Inventory (PTGI) From Baseline to Primary Endpoint
NCT02427568 (12) [back to overview]	Change in Pittsburgh Sleep Quality Inventory (PSQI) From Baseline to Primary Endpoint
NCT03282123 (2) [back to overview]	Change From Baseline to Visit 19 in CAPS-5 Total Severity Scores
NCT03282123 (2) [back to overview]	Change From Baseline to Visit 19 in Adapted SDS Total Score
NCT03485287 (6) [back to overview]	Primary Endpoint Sheehan Disability Scale (SDS for PTSD for MAPS) Total Score
NCT03485287 (6) [back to overview]	Primary Endpoint Clinician-Administered PTSD Scale for DSM-5 (CAPS-5) Total Severity Score
NCT03485287 (6) [back to overview]	Change From Baseline to Primary Endpoint in Sheehan Disability Scale (SDS for PTSD for MAPS) Total Score
NCT03485287 (6) [back to overview]	Change From Baseline to Primary Endpoint in Clinician-Administered PTSD Scale for DSM-5 (CAPS-5) Total Severity Score
NCT03485287 (6) [back to overview]	Baseline Sheehan Disability Scale (SDS for PTSD for MAPS) Total Score
NCT03485287 (6) [back to overview]	Baseline Clinician-Administered PTSD Scale for DSM-5 (CAPS-5) Total Severity Scores
NCT03537014 (2) [back to overview]	Change From Baseline to Primary Endpoint in Sheehan Disability Scale (SDS) Total Score
NCT03537014 (2) [back to overview]	Change From Baseline to Primary Endpoint in Clinician Administered PTSD Scale for DSM-V (CAPS-5)
NCT04077437 (2) [back to overview]	Change From Baseline to Primary Endpoint in Clinician Administered PTSD Scale for DSM-V (CAPS-5)
NCT04077437 (2) [back to overview]	Change From Baseline to Primary Endpoint in Adapted Sheehan Disability Scale (SDS) Total Score

Change in Impact of Events Scale Revised (IES-R) From Baseline to 2-month Follow-up

"The Impact of Events Scale Revised (IES-R) is a 22-item self-report measure (for DSM-IV) designed to measure the extent to which a given stressful life event produces subjective distress. Each item corresponds directly to 14 of the 17 DSM-IV symptoms of PTSD and is rated on a 5-point scale ranging from 0 (not at all) to 4 (extremely) for the extent to which the item was true for the participant during the past seven days. The IES-R yields a total score ranging from 0 to 88 with higher scores indicated greater distress." (NCT00090064)
Timeframe: Baseline to 2 months post second experimental session

Intervention	score on a scale (Mean)
MDMA-assisted Therapy	-29.7
Placebo With Therapy	-12.9

Intervention	score on a scale (Mean)
Full Dose MDMA-assisted Therapy (125 mg)	-15.6
Active Placebo MDMA-assisted Therapy (25 mg)	-3.2

Intervention	score on a scale (Mean)
Full Dose MDMA-assisted Therapy (125 mg)	-8.6
Active Placebo MDMA-assisted Therapy (25 mg)	7.3

Intervention	T-score (Mean)
	Baseline Neuroticism	One month after 2nd Experimental Session Neuroticism	Change in Neuroticism	Baseline Extroversion	One month after 2nd Experimental Session Extroversion	Change in Extroversion	Baseline Openness	One Month after 2nd Experimental Session Openness	Change in Openness	Baseline Agreeableness	One Month after 2nd Experimental Session	Change in Agreeableness	Baseline Conscientiousness	One Month after 2nd Experimental Session Conscientiousness	Change in Conscientiousness
Full Dose MDMA (125 mg)	75.1	58.6	-16.5	34.2	42.2	8.0	57.4	59.4	2.0	39.8	45.7	5.9	41.3	47.8	6.5
Low Dose MDMA (30 mg)	62.0	60.2	-4.6	33.1	36.0	2.2	48.9	49.2	-0.6	44.7	40.6	-1.2	41.3	39.8	-3.2
Medium Dose MDMA (75 mg)	65.3	53.6	-12.0	37.4	46.4	10.0	55.6	66.0	15.6	33.1	33.4	5.4	53.6	56.4	2.4

Intervention	score on a scale (Mean)
Low Dose MDMA (30 mg)	76.0
Medium Dose MDMA (75 mg)	24.1
Full Dose MDMA (125 mg)	45.3

Intervention	score on a scale (Mean)
Low Dose MDMA (30 mg)	-11.6
Medium Dose MDMA (75 mg)	36.1
Full Dose MDMA (125 mg)	33.7

Intervention	score on a scale (Mean)
Low Dose MDMA (30 mg)	1.8
Medium Dose MDMA (75 mg)	-6.4
Full Dose MDMA (125 mg)	-4.8

Intervention	score on a scale (Mean)
Low Dose MDMA (30 mg)	1.1
Medium Dose MDMA (75 mg)	19.4
Full Dose MDMA (125 mg)	18.4

Intervention	score on a scale (Mean)
Low Dose MDMA (30 mg)	-11.4
Medium Dose MDMA (75 mg)	-58.3
Full Dose MDMA (125 mg)	-44.3

Intervention	score on a scale (Mean)
Low Dose MDMA (30 mg)	87.4
Medium Dose MDMA (75 mg)	82.4
Full Dose MDMA (125 mg)	89.7

Intervention	score on a scale (Mean)
Lead in: 125 mg MDMA (Open Label) and Psychotherapy	-23.0
Active Placebo Dose MDMA (25 mg) and Psychotherapy	-10
Full Dose MDMA (125 mg) and Psychotherapy	-20.4

Intervention	score on a scale (Mean)
Lead in: 125 mg MDMA (Open Label) and Psychotherapy	-39.0
Active Placebo Dose MDMA (25 mg) and Psychotherapy	-34.5
Full Dose MDMA (125 mg) and Psychotherapy	-48.8

Intervention	score on a scale (Mean)
Lead in: 125 mg MDMA (Open Label) and Psychotherapy	-42.0
Active Placebo Dose MDMA (25 mg) and Psychotherapy	-9.0
Full Dose MDMA (125 mg) and Psychotherapy	-34.6

Intervention	score on a scale (Mean)
Lead in: 125 mg MDMA (Open Label) and Psychotherapy	-17.0
Active Placebo Dose MDMA (25 mg) and Psychotherapy	-3.5
Full Dose MDMA (125 mg) and Psychotherapy	-18.4

Intervention	score on a scale (Mean)
Lead in: 125 mg MDMA (Open Label) and Psychotherapy	5
Active Placebo Dose MDMA (25 mg) and Psychotherapy	-2.0
Full Dose MDMA (125 mg) and Psychotherapy	26.6

Intervention	score on a scale (Mean)
Lead in: 125 mg MDMA (Open Label) and Psychotherapy	-19.0
Active Placebo Dose MDMA (25 mg) and Psychotherapy	1.33
Full Dose MDMA (125 mg) and Psychotherapy	-17.4

Intervention	score on a scale (Mean)
Lead in: 125 mg MDMA (Open Label) and Psychotherapy	-7.5
Active Placebo Dose MDMA (25 mg) and Psychotherapy	1.0
Full Dose MDMA (125 mg) and Psychotherapy	-1.8

Intervention	score on a scale (Mean)
Lead in: 125 mg MDMA (Open Label) and Psychotherapy	15.0
Active Placebo Dose MDMA (25 mg) and Psychotherapy	-2.33
Full Dose MDMA (125 mg) and Psychotherapy	18.2

Intervention	score on a scale (Mean)
Comparator-dose MDMA (40 mg) and Psychotherapy	23.8
Active Dose 2 MDMA (100 mg) and Psychotherapy	28.2
Active Dose 1 MDMA (125 mg) and Psychotherapy	29.3

Intervention	score on a scale (Mean)
Comparator-dose MDMA (40 mg) and Psychotherapy	12.3
Active Dose 2 MDMA (100 mg) and Psychotherapy	18.3
Active Dose 1 MDMA (125 mg) and Psychotherapy	17.3

Intervention	score on a scale (Mean)
Comparator-dose (40 mg) MDMA and Psychotherapy	-11.5
Active Dose 2 (100 mg) MDMA and Psychotherapy	-9.9
Active Dose 1 (125 mg) MDMA and Psychotherapy	-11.0

n-methyl-3,4-methylenedioxyamphetamine

Description

Cross-References

Synonyms (82)

Research Excerpts

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (1)

Drug Classes (2)

Protein Targets (8)

Inhibition Measurements

Activation Measurements

Other Measurements

Biological Processes (73)

Molecular Functions (41)

Ceullar Components (23)

Bioassays (80)

Research

Studies (4,015)

Market Indicators

Research Demand Index: 20.15

Study Types

Clinical Trials (62)

Trial Overview

Trial Outcomes

Change in Impact of Events Scale Revised (IES-R) From Baseline to 2-month Follow-up

Change in Clinician-Administered PTSD Scale (CAPS-IV) From Baseline to 2-month Follow-up

Change From Baseline to Primary Endpoint in Clinician Administered PTSD Scale for DSM-IV (CAPS-IV)

Change From Baseline to Primary Endpoint in Posttraumatic Stress Diagnostic Scale (PDS)

Change in Clinician-Administered PTSD Scale for DSM-IV (CAPS-IV) at 2-month Follow-up

Change in Clinician-Administered PTSD Scale for DSM-IV (CAPS-IV) at 12-month Follow-up

Change in Clinician-Administered PTSD Scale for DSM-IV (CAPS-IV) at 6-month Follow-up

Change in Neuroticism-Extroversion-Openness Personality Inventory-Revised (NEO-PI-R) From Baseline to Primary Endpoint

Stage 1 Primary Endpoint Clinician-Administered PTSD Scale (CAPS-IV) Total Score

Change in Posttraumatic Growth Inventory (PTGI) From Baseline to Primary Endpoint

Change in Pittsburgh Sleep Quality Index (PSQI) From Baseline to Primary Endpoint

Change in Global Assessment of Function (GAF) From Baseline to Primary Endpoint

Change in Dissociative Experience Scale (DES-II) From Baseline to Primary Endpoint

Change in Clinician-Administered PTSD Scale (CAPS-IV) From Baseline to Primary Endpoint

Change in Beck Depression Inventory (BDI-II) From Baseline to Primary Endpoint

Baseline Clinician-Administered PTSD Scale (CAPS-IV) Total Score

Change in Clinician-Administered PTSD Scale (CAPS-IV) From Baseline to 2-month Follow-up

Clinician-Administered PTSD Scale (CAPS-IV)) at 12-month Follow-up

Clinician-Administered PTSD Scale for DSM-IV (CAPS-IV) at 2-month Follow-up

Baseline Clinician-Administered PTSD Scale for DSM-IV (CAPS-IV)

Change in Clinician-Administered PTSD Scale (CAPS-IV) From Baseline to 12-month Follow-up

Change in Posttraumatic Stress Diagnostic Scale (PDS) Symptom Severity Score From End of Stage 1 to End of Stage 2

Change in Posttraumatic Stress Diagnostic Scale (PDS) Symptom Severity Score From Baseline to Long-Term Follow-Up

Change in Clinical Administered PTSD Scale (CAPS-IV) Total Score From Baseline to Long-Term Follow-Up

Change in Clinical Administered PTSD Scale (CAPS-IV) Total Score From Baseline to End of Stage 1

Change in Beck Depression Inventory (BDI-II) Total Scores From Baseline to Long-Term Follow-Up

Change in Beck Depression Inventory (BDI-II) Total Scores From Baseline to End of Stage 1

Change in Global Assessment of Functioning (GAF) Scale From Baseline to Long-Term Follow-Up

Change in Beck Depression Inventory (BDI-II) Total Score From End of Stage 1 to End of Stage 2

Change in Pittsburgh Sleep Quality Index (PSQI) From End of Stage 1 to End of Stage 2

Change in Posttraumatic Stress Diagnostic Scale (PDS) Symptom Severity Score From Baseline to End of Stage 1

Change in Pittsburgh Sleep Quality Index (PSQI) From Baseline to End of Stage 1

Change in Global Assessment of Functioning (GAF) Scale From End of Stage 1 to End of Stage 2

Change in Global Assessment of Functioning (GAF) Scale From Baseline to End of Stage 1

Change in Clinical Administered PTSD Scale (CAPS-IV) Total Score From End of Stage 1 to End of Stage 2

Change in Pittsburgh Sleep Quality Index (PSQI) From Baseline to Long-Term Follow-Up

Beck Depression Inventory II (BDI-II) at Baseline (ITT)

Beck Depression Inventory II (BDI-II) at One Month Post 2nd Experimental Session (ITT)

Change in Beck Depression Inventory II (BDI-II) From Baseline to One Month Post 2nd Experimental Session (ITT)

Change in Clinician Administered PTSD Scale for DSM-IV (CAPS-IV) Total Severity Score From Baseline to One Month Post 2nd Experimental Session (ITT)

Change in Pittsburgh Sleep Quality Index (PSQI) From Baseline to One Month Post 2nd Experimental Session (ITT)

Clinician Administered PTSD Scale for DSM-IV (CAPS-IV) Total Severity Score at Baseline (ITT)

Clinician Administered PTSD Scale for DSM-IV (CAPS-IV) Total Severity Score at One Month Post 2nd Experimental Session (ITT)

Change in Clinician-Administered PTSD Scale (CAPS-IV) Score From Baseline to Primary Endpoint

Liebowitz Social Anxiety Scale (LSAS) Total Score at Baseline

Liebowitz Social Anxiety Scale (LSAS) Total Score 1-Month Post Experimental Session 2

Change in Leibowitz Social Anxiety Scale (LSAS) Total Score From Baseline to 1-Month Post Experimental Session 2

Change in Death Attitudes Profile (DAP) From Baseline to Primary Endpoint

Change in MADRS Score From Baseline to Primary Endpoint

Change in Global Assessment of Functioning (GAF) Score From Baseline to Primary Endpoint

Change in Beck Depression Inventory-II (BDI-II) Score From Baseline to Primary Endpoint

Baseline STAI Trait Score

Intervention	score on a scale (Mean)
Comparator-dose (40 mg) MDMA and Psychotherapy	-0.83
Active Dose 2 (100 mg) MDMA and Psychotherapy	-3.56
Active Dose 1 (125 mg) MDMA and Psychotherapy	-1.92

Intervention	score on a scale (Mean)
Comparator-dose MDMA (40 mg) and Psychotherapy	84.8
Active Dose 2 MDMA (100 mg) and Psychotherapy	94.4
Active Dose 1 MDMA (125 mg) and Psychotherapy	93.5

Intervention	score on a scale (Mean)
Comparator-dose MDMA (40 mg) and Psychotherapy	73.3
Active Dose 2 MDMA (100 mg) and Psychotherapy	70.0
Active Dose 1 MDMA (125 mg) and Psychotherapy	64.3

Intervention	score on a scale (Mean)
Inactive Placebo With Psychotherapy	83.3
75 mg to 125 mg MDMA With Psychotherapy	91.8

Intervention	score on a scale (Mean)
Inactive Placebo With Psychotherapy	64.0
75 mg to 125 mg MDMA With Psychotherapy	46.4

Intervention	score on a scale (Mean)
Inactive Placebo With Psychotherapy	-19.3
75 mg to 125 mg MDMA With Psychotherapy	-44.1

Intervention	score on a scale (Mean)
	Fear of death	Death avoidance	Neutral acceptance	Approach acceptance	Escape acceptance
MDMA-assisted Therapy (125 mg)	-0.1	0	0.1	0.3	0.4
Placebo With Therapy	-0.6	-1.1	0.2	-0.1	0

Intervention	score on a scale (Mean)
Placebo With Therapy	-14.6
MDMA-assisted Therapy (125 mg)	-20.9

Intervention	score on a scale (Mean)
	Physical well-being	Social/ family well-being	Emotional well-being	Functional well-being	Additional concerns
MDMA-assisted Therapy (125 mg)	1.4	0.8	1.6	4.8	4.5
Placebo With Therapy	2.8	-2.0	1.0	1.0	-0.3

Intervention	score on a scale (Mean)
Experimental: MDMA-assisted Psychotherapy	-23.5
Placebo Comparator: Placebo With Psychotherapy	-15.4