Page last updated: 2024-11-04

3,4-methylenedioxyamphetamine

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Description

3,4-Methylenedioxyamphetamine: An amphetamine derivative that inhibits uptake of catecholamine neurotransmitters. It is a hallucinogen. It is less toxic than its methylated derivative but in sufficient doses may still destroy serotonergic neurons and has been used for that purpose experimentally. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1614
CHEMBL ID6731
CHEBI ID166520
SCHEMBL ID393456
MeSH IDM0023232

Synonyms (75)

Synonym
1-(1,3-benzodioxol-5-yl)propan-2-amine
CHEBI:166520
1,3-benzodioxole,5-ethanamine-.alpha.-methyl-(.+/-.)
phenethylamine, .alpha.-methyl-3,4-(methylenedioxy)-
DIVK1C_000964
KBIO1_000964
IDI1_000964
tenamfetaminum [latin]
tenamfetamina [spanish]
tenamfetamine [inn]
PDSP2_001394
dl-alpha-methyl-3,4-(methylenedioxy)phenylethylamine
4764-17-4
(+/-)-3,4-(methylenedioxy)amphetamine
5-(2-aminopropyl)-1,3-benzodioxole
alpha-methyl-3,4-(methylenedioxy)phenethylamine
phenethylamine, alpha-methyl-3,4-(methylenedioxy)-
ai3-24882
1-(3,4-methylenedioxyphenyl)-2-propylamine
(r,s)-3,4-methylenedioxyamphetamine
alpha-methyl-1,3-benzodioxole-5-ethanamine
ea-1299
mda (pharmaceutical)
5-19-08-00417 (beilstein handbook reference)
3,4-(methylenedioxy)-alpha-methylphenylethylamine
3,4-methylenedioxyamphetamine
1,3-benzodioxole-5-ethanamine, alpha-methyl- (9ci)
3,4-methylenedioxy-amphetamine
methylenedioxyamphetamine
brn 0150196
3,4-methylenedioxy-alpha-methyl-beta-phenylethylamine
love
alpha-methyl-3,4-methylenedioxyphenethylamine
1,3-benzodioxole-5-ethanamine, alpha-methyl-
tenamfetamine
dea no. 7400
DB01509
NINDS_000964
PDSP1_001410
CHEMBL6731 ,
skf-5
methylene dioxyamphetamine
AKOS002433952
(+/-)2-benzo[1,3]dioxol-5-yl-1-methyl-ethylamine
2-benzo[1,3]dioxol-5-yl-1-methyl-ethylamine
mda,r(-)
(r)-(-)-2-benzo[1,3]dioxol-5-yl-1-methyl-ethylamine
(s)-(+)-2-benzo[1,3]dioxol-5-yl-1-methyl-ethylamine
mda, (r,s)
bdbm50005247
(-)2-benzo[1,3]dioxol-5-yl-1-methyl-ethylamine
2-benzo[1,3]dioxol-5-yl-1-methyl-ethylamine((r)-(-)-mda)
hsdb 7593
tenamfetaminum
unii-xjz28fj27w
xjz28fj27w ,
tenamfetamina
tenamfetamine [mart.]
mda (psychedelic)
(+/-)-.alpha.-methyl-3,4-(methylenedioxy)phenethylamine
mda [mi]
tenamfetamine [who-dd]
SCHEMBL393456
.alpha.-methyl-3,4-methylenedioxyphenethylamine
.alpha.-methyl-3,4-(methylenedioxy)phenethylamine
1,3-benzodioxole-5-ethanamine, .alpha.-methyl-
51497-09-7
1-(2h-1,3-benzodioxol-5-yl)propan-2-amine
rac-mda (rac-3,4-methylenedioxyamphetamine) 1.0 mg/ml in methanol
1-(benzo[d][1,3]dioxol-5-yl)propan-2-amine
3,4-methylenedioxyamphetamine (mda)
FT-0739487
DTXSID40859958
(-)-tenamfetamine
Q223020

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"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
" These findings suggest that neither of MDA's major metabolites mediate its toxic effects on 5-HT neurons and that either a minor metabolite is responsible or that alternate mechanisms are involved."( Major metabolites of (+/-)3,4-methylenedioxyamphetamine (MDA) do not mediate its toxic effects on brain serotonin neurons.
McCann, UD; Ricaurte, GA, 1991
)
0.58
" 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
)
0.83
"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
" Toxicity studies showed all of the compounds to have LD50 values similar to N-methyl MDA (MDMA)."( Synthesis, identification, and acute toxicity of some N-alkyl derivatives of 3,4-methylenedioxyamphetamine.
Clark, CR; Coker, ST; DeRuiter, J; Noggle, FT,
)
0.36
" 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
"The way in which sex may be constructed as safe through its relationship with 'love' is the concern of this study."( Safe sex or safe love: competing discourses?
Gifford, S; Moore, S; Rosenthal, D, 1998
)
0.3
" The restraint manipulation is utilized as a technique to characterize the physiological, cellular and molecular consequences of stress as well as a tool to understand the ways in which stress may interact with toxic substances."( Restraint as a stressor in mice: against the dopaminergic neurotoxicity of D-MDMA, low body weight mitigates restraint-induced hypothermia and consequent neuroprotection.
Johnson, EA; Miller, DB; Sharp, DS, 2000
)
0.31
" The toxic effects induced following incubation of hepatocyte suspensions with these metabolites were evaluated by measuring cell viability, the extent of lipid peroxidation, levels of glutathione (GSH) and glutathione disulfide (GSSG), the formation of GSH conjugates, and the activities of GSSG reductase (GR), GSH peroxidase (GPX), and GSH S-transferase (GST)."( Hepatotoxicity of 3,4-methylenedioxyamphetamine and alpha-methyldopamine in isolated rat hepatocytes: formation of glutathione conjugates.
Amado, F; Bastos, ML; Borges, F; Carvalho, F; Carvalho, M; Fernandes, E; Milhazes, N; Monks, TJ; Remião, F, 2004
)
0.66
" The indirect effect of MDMA mediated by a sustained high level of circulating biogenic amines may contribute to the cardiotoxic effects, but other factors, like the direct toxic effects of MDMA and its metabolites in cardiac cells, remain to be investigated."( Metabolism is required for the expression of ecstasy-induced cardiotoxicity in vitro.
Amado, F; Bastos, ML; Borges, F; Carvalho, F; Carvalho, M; Fernandes, E; Gonçalves, MJ; Milhazes, N; Monteiro, Mdo C; Remião, F; Seabra, V, 2004
)
0.32
"In mice, the recreational drug (+/-)3,4-methylenedioxymethamphetamine [MDMA ("ecstasy")] produces a selective toxic effect on brain dopamine (DA) neurons."( Identification and characterization of metallothionein-1 and -2 gene expression in the context of (+/-)3,4-methylenedioxymethamphetamine-induced toxicity to brain dopaminergic neurons.
Becker, KG; Cheadle, C; Donovan, DM; McCann, UD; Mechan, AO; Ricaurte, GA; Tong, L; Xie, T; Yuan, J, 2004
)
0.32
"XTC and other amphetamines are considered to be safe by the majority of partying young people who are unaware of (or unwilling to know about) the acute and chronic toxicity of these substances, and these drugs are widespread, illicit stimulants."( Amphetamine toxicity in the emergency department.
Bronselaer, K; De Feyter, K; De Munnynck, K; Sabbe, M; Smets, G; Van de Voorde, W, 2005
)
0.33
" The results of the comparative toxicity study, using undifferentiated PC12 cells, strongly suggest that the metabolites possessing a catecholic group are more toxic to the cells than MDMA and metabolites with at least one protected phenolic group."( Synthesis and cytotoxic profile of 3,4-methylenedioxymethamphetamine ("ecstasy") and its metabolites on undifferentiated PC12 cells: A putative structure-toxicity relationship.
Borges, F; Cunha-Oliveira, T; Garrido, J; Martins, P; Milhazes, N; Oliveira, C; Rego, AC, 2006
)
0.33
"3,4-Methylenedioxymethamphetamine (MDMA)'s O-demethylenated metabolite, 3,4-dihydroxymethamphetamine (HHMA), has been hypothesized to serve as a precursor for the formation of toxic catechol-thioether metabolites (e."( Inhibition of 3,4-methylenedioxymethamphetamine metabolism leads to marked decrease in 3,4-dihydroxymethamphetamine formation but no change in serotonin neurotoxicity: implications for mechanisms of neurotoxicity.
Maldonado Adrian, C; McCann, UD; Mueller, M; Ricaurte, GA; Yuan, J, 2011
)
0.37
" The drug is generally thought to be safe among consumers due to its low-mortality rates."( A mechanistic insight into 3,4-methylenedioxymethamphetamine ("ecstasy")-mediated hepatotoxicity.
Antolino-Lobo, I; Meulenbelt, J; van den Berg, M; van Duursen, MB, 2011
)
0.37
" 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
" Our findings support the view that COMT plays a pivotal role in determining the toxic response to MDMA."( Catechol-o-methyltransferase and 3,4-({+/-})-methylenedioxymethamphetamine toxicity.
Cholanians, AB; Herndon, JM; Lau, SS; Lizarraga, LE; Monks, TJ, 2014
)
0.4

Pharmacokinetics

The metabolism and disposition of N-hydroxy-3,4-methylenedioxyamphetamine (N-OH MDA) was studied by utilizing rat liver slices as well as by intravenous pharmacokinetic studies in rats.

ExcerptReferenceRelevance
"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,
)
0.35
"The metabolism and disposition of N-hydroxy-3,4-methylenedioxyamphetamine (N-OH MDA) was studied by utilizing rat liver slices as well as by intravenous pharmacokinetic studies in rats."( The pharmacokinetics and liver metabolism of N-hydroxy-3,4-methylenedioxyamphetamine (N-OH MDA) in rats.
Brzozowski, D; Clark, CR; Ravis, WR; Valaer, AK, 1994
)
0.8
" 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
" 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
" Curiously, the approximate elimination half-life (t(1/2)) of MDMA at 18 degrees C (136 min) and 31 degrees C (144 min) was increased compared with 24 degrees C (90 min) and is most likely because of volume of distribution changes induced by core temperature alterations."( Ambient temperature effects on 3,4-methylenedioxymethamphetamine-induced thermodysregulation and pharmacokinetics in male monkeys.
Banks, ML; Czoty, PW; Kisor, DF; Nader, MA; Nichols, DE; Sprague, JE, 2007
)
0.34
" 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
" A total of 31 healthy Chinese subjects participated in the pharmacokinetic study of single bolus intravenous injection of piperphentonamine hydrochloride."( Determination of piperphentonamine and metabolites M1 and M6 in human plasma and urine by LC/MS/MS and its application in a pharmacokinetics study in Chinese healthy volunteers.
Han, L; Hu, X; Li, J; Li, K; Li, R; Shi, A; Wan, H, 2012
)
0.38
" 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
"Generally, pharmacokinetic studies on 3,4-methylenedioxymethamphetamine (MDMA) in blood have been performed after conjugate cleavage, without taking into account that phase II metabolites represent distinct chemical entities with their own effects and stereoselective pharmacokinetics."( Chiral Plasma Pharmacokinetics of 3,4-Methylenedioxymethamphetamine and its Phase I and II Metabolites following Controlled Administration to Humans.
Kraemer, T; Liechti, ME; Rickli, A; Schmid, Y; Schmidhauser, C; Steuer, AE, 2015
)
0.42

Bioavailability

ExcerptReferenceRelevance
" 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

Dosage Studied

ExcerptRelevanceReference
" The amount of metabolite increased on hydrolyzing the urine from dosed dogs and monkeys with a preparation containing beta-glucuronidase and sulfatase."( Identification of 3-O-methyl-alpha-methyldopamine as a urinary metabolite of 3,4-methylenedioxyamphetamine in dog and monkey.
By, A; Cooper, JK; Ethier, JC; Midha, KK,
)
0.36
" 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
)
0.57
" 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
" In addition to these salient features, the results of this study also have an impact on stimulus specificity, and further emphasize the importance of thorough dose-response relationships as related to tests of stimulus generalization."( MDA: a psychoactive agent with dual stimulus effects.
Glennon, RA; Young, R, 1984
)
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
" 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
" 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
" 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 present study was aimed at investigating the direct effects of CsA and Cre on isolated and perfused rat hearts in the dosage that closely approximates the peak level achieved for the prevention of graft rejection in the rat."( Effects of cyclosporin and cremophor on working rat heart and incidence of myocardial lipid peroxidation.
David, M; Gabrielle, F; Maupoil, V; Mossiat, C; Rochette, L; Tatou, E, 1996
)
0.29
"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
" 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
" 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
" 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
"The purpose of the current study was to extend previous results on the acute effects of MDMA on behavioral thermoregulation to a repeated dosing regime, simulating regular weekend use of ecstasy, on measures of thermoregulation and heart rate (HR)."( The effect of long-term repeated exposure to 3,4-methylenedioxymethamphetamine on cardiovascular and thermoregulatory changes.
Irvine, RJ; Jaehne, EJ; Salem, A, 2008
)
0.35
" HR responses to MDMA over 6 weeks at both TAs progressively decreased with repeated dosing (P<0."( The effect of long-term repeated exposure to 3,4-methylenedioxymethamphetamine on cardiovascular and thermoregulatory changes.
Irvine, RJ; Jaehne, EJ; Salem, A, 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
"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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
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 Targets (19)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki2.50120.00020.667710.0000AID4760; AID4762; AID5263
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki2.80750.00010.601710.0000AID5263
Sodium-dependent noradrenaline transporter Homo sapiens (human)IC50 (µMol)1.23140.00081.541620.0000AID471667; AID488693; AID752492
Sodium-dependent noradrenaline transporter Homo sapiens (human)Ki0.70400.00031.465610.0000AID752492
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Ki2.80750.00020.590910.0000AID5263
Sodium-dependent serotonin transporterHomo sapiens (human)IC50 (µMol)2.71290.00010.86458.7096AID488692; AID576813; AID752491
Sodium-dependent serotonin transporterHomo sapiens (human)Ki2.30600.00000.70488.1930AID752491
Sodium-dependent serotonin transporterRattus norvegicus (Norway rat)IC50 (µMol)0.99600.00030.81978.4900AID471630
Sodium-dependent dopamine transporter Homo sapiens (human)IC50 (µMol)2.64860.00071.841946.0000AID471668; AID488694; AID752493
Sodium-dependent dopamine transporter Homo sapiens (human)Ki2.42500.00021.11158.0280AID752493
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Kd0.35480.00042.58328.5114AID6406
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Kd0.35480.00012.62198.5114AID6406
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Kd0.35480.00012.29338.5114AID6406
Sodium-dependent dopamine transporterRattus norvegicus (Norway rat)EC50 (µMol)0.19000.00070.17911.4500AID1442370
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Kd0.35480.02342.74218.5114AID6406
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Kd0.35480.02342.74218.5114AID6406
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Kd0.35480.02342.74218.5114AID6406
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Kd0.35480.00042.47358.5114AID6406
5-hydroxytryptamine receptor 6Rattus norvegicus (Norway rat)Kd0.35480.02342.74218.5114AID6406
Sodium-dependent serotonin transporterHomo sapiens (human)EC50 (µMol)1,298.64550.00112.38838.7000AID471635; AID471638
Sodium-dependent serotonin transporterRattus norvegicus (Norway rat)EC50 (µMol)0.16000.00070.42361.7650AID1442369
5-hydroxytryptamine receptor 7 Rattus norvegicus (Norway rat)Kd0.35480.00012.70068.5114AID6406
5-hydroxytryptamine receptor 5ARattus norvegicus (Norway rat)Kd0.35480.02342.74218.5114AID6406
5-hydroxytryptamine receptor 5BRattus norvegicus (Norway rat)Kd0.35480.02342.74218.5114AID6406
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)Kd0.35480.00082.62148.5114AID6406
5-hydroxytryptamine receptor 4 Rattus norvegicus (Norway rat)Kd0.35480.02342.74218.5114AID6406
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)Kd0.35480.00082.62148.5114AID6406
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (55)

Processvia Protein(s)Taxonomy
monoamine transportSodium-dependent noradrenaline transporter Homo sapiens (human)
neurotransmitter transportSodium-dependent noradrenaline transporter Homo sapiens (human)
chemical synaptic transmissionSodium-dependent noradrenaline transporter Homo sapiens (human)
response to xenobiotic stimulusSodium-dependent noradrenaline transporter Homo sapiens (human)
response to painSodium-dependent noradrenaline transporter Homo sapiens (human)
norepinephrine uptakeSodium-dependent noradrenaline transporter Homo sapiens (human)
neuron cellular homeostasisSodium-dependent noradrenaline transporter Homo sapiens (human)
amino acid transportSodium-dependent noradrenaline transporter Homo sapiens (human)
norepinephrine transportSodium-dependent noradrenaline transporter Homo sapiens (human)
dopamine uptake involved in synaptic transmissionSodium-dependent noradrenaline transporter Homo sapiens (human)
sodium ion transmembrane transportSodium-dependent noradrenaline transporter Homo sapiens (human)
monoamine transportSodium-dependent serotonin transporterHomo sapiens (human)
response to hypoxiaSodium-dependent serotonin transporterHomo sapiens (human)
neurotransmitter transportSodium-dependent serotonin transporterHomo sapiens (human)
response to nutrientSodium-dependent serotonin transporterHomo sapiens (human)
memorySodium-dependent serotonin transporterHomo sapiens (human)
circadian rhythmSodium-dependent serotonin transporterHomo sapiens (human)
response to xenobiotic stimulusSodium-dependent serotonin transporterHomo sapiens (human)
response to toxic substanceSodium-dependent serotonin transporterHomo sapiens (human)
positive regulation of gene expressionSodium-dependent serotonin transporterHomo sapiens (human)
positive regulation of serotonin secretionSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of cerebellar granule cell precursor proliferationSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of synaptic transmission, dopaminergicSodium-dependent serotonin transporterHomo sapiens (human)
response to estradiolSodium-dependent serotonin transporterHomo sapiens (human)
social behaviorSodium-dependent serotonin transporterHomo sapiens (human)
vasoconstrictionSodium-dependent serotonin transporterHomo sapiens (human)
sperm ejaculationSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of neuron differentiationSodium-dependent serotonin transporterHomo sapiens (human)
positive regulation of cell cycleSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of organ growthSodium-dependent serotonin transporterHomo sapiens (human)
behavioral response to cocaineSodium-dependent serotonin transporterHomo sapiens (human)
enteric nervous system developmentSodium-dependent serotonin transporterHomo sapiens (human)
brain morphogenesisSodium-dependent serotonin transporterHomo sapiens (human)
serotonin uptakeSodium-dependent serotonin transporterHomo sapiens (human)
membrane depolarizationSodium-dependent serotonin transporterHomo sapiens (human)
platelet aggregationSodium-dependent serotonin transporterHomo sapiens (human)
cellular response to retinoic acidSodium-dependent serotonin transporterHomo sapiens (human)
cellular response to cGMPSodium-dependent serotonin transporterHomo sapiens (human)
regulation of thalamus sizeSodium-dependent serotonin transporterHomo sapiens (human)
conditioned place preferenceSodium-dependent serotonin transporterHomo sapiens (human)
sodium ion transmembrane transportSodium-dependent serotonin transporterHomo sapiens (human)
amino acid transportSodium-dependent serotonin transporterHomo sapiens (human)
monoamine transportSodium-dependent dopamine transporter Homo sapiens (human)
neurotransmitter transportSodium-dependent dopamine transporter Homo sapiens (human)
lactationSodium-dependent dopamine transporter Homo sapiens (human)
sensory perception of smellSodium-dependent dopamine transporter Homo sapiens (human)
locomotory behaviorSodium-dependent dopamine transporter Homo sapiens (human)
response to xenobiotic stimulusSodium-dependent dopamine transporter Homo sapiens (human)
response to iron ionSodium-dependent dopamine transporter Homo sapiens (human)
dopamine transportSodium-dependent dopamine transporter Homo sapiens (human)
adenohypophysis developmentSodium-dependent dopamine transporter Homo sapiens (human)
response to nicotineSodium-dependent dopamine transporter Homo sapiens (human)
positive regulation of multicellular organism growthSodium-dependent dopamine transporter Homo sapiens (human)
regulation of dopamine metabolic processSodium-dependent dopamine transporter Homo sapiens (human)
response to cocaineSodium-dependent dopamine transporter Homo sapiens (human)
dopamine biosynthetic processSodium-dependent dopamine transporter Homo sapiens (human)
dopamine catabolic processSodium-dependent dopamine transporter Homo sapiens (human)
response to ethanolSodium-dependent dopamine transporter Homo sapiens (human)
cognitionSodium-dependent dopamine transporter Homo sapiens (human)
dopamine uptake involved in synaptic transmissionSodium-dependent dopamine transporter Homo sapiens (human)
response to cAMPSodium-dependent dopamine transporter Homo sapiens (human)
norepinephrine uptakeSodium-dependent dopamine transporter Homo sapiens (human)
prepulse inhibitionSodium-dependent dopamine transporter Homo sapiens (human)
dopamine uptakeSodium-dependent dopamine transporter Homo sapiens (human)
hyaloid vascular plexus regressionSodium-dependent dopamine transporter Homo sapiens (human)
amino acid transportSodium-dependent dopamine transporter Homo sapiens (human)
norepinephrine transportSodium-dependent dopamine transporter Homo sapiens (human)
sodium ion transmembrane transportSodium-dependent dopamine transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (28)

Processvia Protein(s)Taxonomy
actin bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
neurotransmitter transmembrane transporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
neurotransmitter:sodium symporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
dopamine:sodium symporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
norepinephrine:sodium symporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
protein bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
monoamine transmembrane transporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
alpha-tubulin bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
metal ion bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
beta-tubulin bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
integrin bindingSodium-dependent serotonin transporterHomo sapiens (human)
monoatomic cation channel activitySodium-dependent serotonin transporterHomo sapiens (human)
neurotransmitter transmembrane transporter activitySodium-dependent serotonin transporterHomo sapiens (human)
serotonin:sodium:chloride symporter activitySodium-dependent serotonin transporterHomo sapiens (human)
protein bindingSodium-dependent serotonin transporterHomo sapiens (human)
monoamine transmembrane transporter activitySodium-dependent serotonin transporterHomo sapiens (human)
antiporter activitySodium-dependent serotonin transporterHomo sapiens (human)
syntaxin-1 bindingSodium-dependent serotonin transporterHomo sapiens (human)
cocaine bindingSodium-dependent serotonin transporterHomo sapiens (human)
sodium ion bindingSodium-dependent serotonin transporterHomo sapiens (human)
identical protein bindingSodium-dependent serotonin transporterHomo sapiens (human)
nitric-oxide synthase bindingSodium-dependent serotonin transporterHomo sapiens (human)
actin filament bindingSodium-dependent serotonin transporterHomo sapiens (human)
serotonin bindingSodium-dependent serotonin transporterHomo sapiens (human)
protease bindingSodium-dependent dopamine transporter Homo sapiens (human)
signaling receptor bindingSodium-dependent dopamine transporter Homo sapiens (human)
neurotransmitter transmembrane transporter activitySodium-dependent dopamine transporter Homo sapiens (human)
dopamine:sodium symporter activitySodium-dependent dopamine transporter Homo sapiens (human)
protein bindingSodium-dependent dopamine transporter Homo sapiens (human)
monoamine transmembrane transporter activitySodium-dependent dopamine transporter Homo sapiens (human)
dopamine bindingSodium-dependent dopamine transporter Homo sapiens (human)
amine bindingSodium-dependent dopamine transporter Homo sapiens (human)
protein-containing complex bindingSodium-dependent dopamine transporter Homo sapiens (human)
metal ion bindingSodium-dependent dopamine transporter Homo sapiens (human)
protein phosphatase 2A bindingSodium-dependent dopamine transporter Homo sapiens (human)
heterocyclic compound bindingSodium-dependent dopamine transporter Homo sapiens (human)
norepinephrine:sodium symporter activitySodium-dependent dopamine transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (19)

Processvia Protein(s)Taxonomy
plasma membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
cell surfaceSodium-dependent noradrenaline transporter Homo sapiens (human)
membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
neuronal cell body membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
presynaptic membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
plasma membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
axonSodium-dependent noradrenaline transporter Homo sapiens (human)
plasma membraneSodium-dependent serotonin transporterHomo sapiens (human)
focal adhesionSodium-dependent serotonin transporterHomo sapiens (human)
endosome membraneSodium-dependent serotonin transporterHomo sapiens (human)
endomembrane systemSodium-dependent serotonin transporterHomo sapiens (human)
presynaptic membraneSodium-dependent serotonin transporterHomo sapiens (human)
membrane raftSodium-dependent serotonin transporterHomo sapiens (human)
synapseSodium-dependent serotonin transporterHomo sapiens (human)
postsynaptic membraneSodium-dependent serotonin transporterHomo sapiens (human)
serotonergic synapseSodium-dependent serotonin transporterHomo sapiens (human)
synapseSodium-dependent serotonin transporterHomo sapiens (human)
plasma membraneSodium-dependent serotonin transporterHomo sapiens (human)
neuron projectionSodium-dependent serotonin transporterHomo sapiens (human)
cytoplasmSodium-dependent dopamine transporter Homo sapiens (human)
plasma membraneSodium-dependent dopamine transporter Homo sapiens (human)
cell surfaceSodium-dependent dopamine transporter Homo sapiens (human)
membraneSodium-dependent dopamine transporter Homo sapiens (human)
axonSodium-dependent dopamine transporter Homo sapiens (human)
neuron projectionSodium-dependent dopamine transporter Homo sapiens (human)
neuronal cell bodySodium-dependent dopamine transporter Homo sapiens (human)
axon terminusSodium-dependent dopamine transporter Homo sapiens (human)
membrane raftSodium-dependent dopamine transporter Homo sapiens (human)
postsynaptic membraneSodium-dependent dopamine transporter Homo sapiens (human)
dopaminergic synapseSodium-dependent dopamine transporter Homo sapiens (human)
flotillin complexSodium-dependent dopamine transporter Homo sapiens (human)
axonSodium-dependent dopamine transporter Homo sapiens (human)
presynaptic membraneSodium-dependent dopamine transporter Homo sapiens (human)
plasma membraneSodium-dependent dopamine transporter Homo sapiens (human)
neuronal cell body membraneSodium-dependent dopamine transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (71)

Assay IDTitleYearJournalArticle
AID180304Inhibitory concentration against [3H]- NE uptake in crude rat synaptosomes1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine.
AID23503Partition coefficient (logP)1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.
AID752492Inhibition 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 assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'.
AID234658selectivity is the ratio between IC50 values of 5-HTand DA1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA).
AID204225Activity towards Serotonin transporter was determined by the ability to inhibit [3H]5-HT uptake in rat synaptosomes1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA).
AID90250Human hallucinogenic activity relative to mescaline1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.
AID1131956Hallucinogenic activity in human1977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Structure-activity studies on hallucinogenic amphetamines using molecular connectivity.
AID576803Cytotoxicity against human SH-SY5Y cells expressing human SERT assessed as decrease in cell viability after 48 hrs neutral red dye assay2011Bioorganic & 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.
AID752493Inhibition 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 assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'.
AID576805Cytotoxicity against human chemoresistant DG75 cells expressing SERT assessed as decrease in cell viability 10 or 50 uM after 72 hrs Alamar blue assay2011Bioorganic & 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.
AID91217Compound tested for hallucinogenic activity in humans was reported; Value reported in (A)= Mescaline units1998Journal of medicinal chemistry, Sep-24, Volume: 41, Issue:20
The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens.
AID1130887Induction of hyperactivity in Swiss Webster mouse assessed as salivation at 0.025 to 0.3 mmol/kg, ip up to 90 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
AID1442369Activity at SERT in rat synaptosomes assessed as release of [3H]HT after 5 mins by liquid scintillation counting method2017Journal 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.
AID488693Binding affinity to human NET2010Bioorganic & 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.
AID576813Inhibition of [3H]-serotonin reuptake at human SERT expressed in HEK293 cells after 15 to 20 mins by fluorescence neurotransmitter transporter assay2011Bioorganic & 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.
AID88883Hallucinogenic activity i.e; ratio of effective dose of mescaline to the effective dose in human1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.
AID1442368Displacement of [3H]ketanserin from 5HT2A in Sprague-Dawley rat frontal cortex membranes measured after 15 mins by scintillation counting method2017Journal 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.
AID488696Cytotoxicity against human HEK293 cells over expressing human SERT assessed as cell viability after 48 hrs by neutral red assay2010Bioorganic & 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.
AID4762Binding affinity towards 5-hydroxytryptamine 1C receptor from frontal cortical regions of male Sprague-Dawley rat homogenates, using [3H]mesulergine as radioligand1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.
AID167866Hyperthermic potency in rabbit relative to DOM1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.
AID179206Compound was tested for its ability to inhibit [3H]dopamine uptake in rat synaptosomes1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA).
AID1442373Induction of stimulus generalization in rat trained to discriminate PMMA assessed as appropriate responding level to training drug by two lever method2017Journal 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.
AID5263Binding affinity towards 5-hydroxytryptamine 2 receptor from frontal cortical regions of male Sprague-Dawley rat homogenates, using [3H]ketanserin as radioligand1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.
AID180302Inhibitory concentration against [3H]- DA uptake in crude rat synaptosomes1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine.
AID488697Cytotoxicity against human HEK293 cells over expressing human NET assessed as cell viability after 48 hrs by neutral red assay2010Bioorganic & 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.
AID178403Effective dose in rats trained on 1 mg/kg DOM.1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.
AID488695Cytotoxicity against human HEK293 cells assessed as cell viability after 48 hrs by neutral red assay2010Bioorganic & 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.
AID471635Induction of human SERT-dependent cytotoxicity in SERT expressing HEK293 cells after 48 hrs by neutral red assay2009European 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.
AID5797Affinity against 5-hydroxytryptamine 2B receptor in the isolated rat stomach fundus1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.
AID1130884Induction of hyperactivity in Swiss Webster mouse assessed as exploratory behavior at 0.025 to 0.3 mmol/kg, ip up to 90 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
AID752491Inhibition 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 assay2013Bioorganic & medicinal chemistry letters, Jun-01, Volume: 23, Issue:11
An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'.
AID1130919Induction of spontaneous activity in Swiss Webster mouse assessed as spontaneous activity counts at 0.30 mmol/kg, ip measured over 90 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
AID471638Induction of human SERT-dependent cytotoxicity in SERT expressing human DG75 cells after 48 hrs by neutral red assay2009European 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.
AID471639Cytotoxicity against human SH-SY5Y cells after 48 hrs by neutral red assay2009European 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.
AID576811Cytotoxicity against human HEK293 cells assessed as decrease in cell viability after 48 hrs neutral red dye assay2011Bioorganic & 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.
AID471667Inhibition of human noradrenaline transporter2009European 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.
AID234659selectivity is the ratio between IC50 values of 5-HTand NE1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA).
AID178354Compound was tested for hallucinogenic activity in rats at 0.32(mg/kg)1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.
AID471665Inhibition of [3H]5-HT uptake at SERT in rat brain synaptosome2009European 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.
AID471630Inhibition of [3H]5-HT reuptake at rat SERT expressed in HEK293 cells after 2 mins by liquid scintillation counting2009European 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.
AID1442370Activity at DAT in rat synaptosomes assessed as release of [3H]DA after 5 mins by liquid scintillation counting method2017Journal 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.
AID1130888Induction of hyperactivity in Swiss Webster mouse assessed as grooming at 0.025 to 0.3 mmol/kg, ip up to 90 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
AID225285Effective dose for drug discrimination assay in rats using (+)-MBDB as training drug.1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA).
AID1130917Induction of spontaneous activity in Swiss Webster mouse assessed as spontaneous activity counts at 0.075 mmol/kg, ip measured over 90 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
AID1130915Octanol-water partition coefficient, log P of the compound1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
AID191080Compound was tested for hallucinogenic activity in rats at 0.32dose (mg/kg); Number of rats selecting the LSD lever/ number of rats responding (0/8)1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.
AID191209Compound was tested for hallucinogenic activity in rats at 1.29 dose(mg/kg); Number of rats selecting the LSD lever/ number of rats responding (5/8)1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.
AID1130916Induction of spontaneous activity in Swiss Webster mouse assessed as spontaneous activity counts at 0.025 mmol/kg, ip measured over 90 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
AID1146450Competitive antagonist activity at 5-HT serotonin receptor in Sprague-Dawley rat stomach fundus model assessed as inhibition of 5-HT-induced contractile response1978Journal of medicinal chemistry, Aug, Volume: 21, Issue:8
Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues.
AID145706Compound was tested for the ability to inhibit [3H]norepinephrine binding to Norepinephrine transporter in rat synaptosomes1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA).
AID488692Binding affinity to human SERT2010Bioorganic & 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.
AID471634Cytotoxicity against human HEK293 cells after 48 hrs by neutral red assay2009European 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.
AID471668Inhibition of human dopamine transporter2009European 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.
AID227926Equilibrium constant for DNB complex formation1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.
AID488698Cytotoxicity against human HEK293 cells over expressing human DAT assessed as cell viability after 48 hrs by neutral red assay2010Bioorganic & 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.
AID19263Log value of hallucinogenic activity was determined1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.
AID180301Inhibitory concentration against [3H]- 5-HT uptake in crude rat synaptosomes1993Journal of medicinal chemistry, Nov-12, Volume: 36, Issue:23
Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine.
AID191081Compound was tested for hallucinogenic activity in rats at 0.63 dose(mg/kg); Number of rats selecting the LSD lever/ number of rats responding (2/8)1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.
AID576812Cytotoxicity against human HEK293 cells expressing human SERT assessed as decrease in cell viability after 48 hrs neutral red dye assay2011Bioorganic & 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.
AID1442371Activity at NET in rat synaptosomes assessed as release of [3H]NE after 30 mins by liquid scintillation counting method2017Journal 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.
AID1130885Induction of hyperactivity in Swiss Webster mouse assessed as pilomotor erection at 0.025 to 0.3 mmol/kg, ip up to 90 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
AID178356Compound was tested for hallucinogenic activity in rats at the dose 0 (mg/kg)1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.
AID191215Compound was tested for hallucinogenic activity in rats at 1.72 dose(mg/kg); Number of rats selecting the LSD lever/ number of rats responding (7/8)1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class.
AID4760Compound was tested for binding affinity towards 5-HT1C (5-HT1C) receptor from frontal cortical regions of male Sprague-Dawley rat homogenates, using [3H]mesulergine as radioligand1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.
AID1130883Induction of hyperactivity in Swiss Webster mouse assessed as exopthalmia at 0.025 to 0.3 mmol/kg, ip up to 90 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
AID488694Binding affinity to human DAT2010Bioorganic & 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.
AID2330285-HT1C selectivity was defined as the ratio between Ki(5-HT2)/Ki(5-HT1C)1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.
AID1130918Induction of spontaneous activity in Swiss Webster mouse assessed as spontaneous activity counts at 0.225 mmol/kg, ip measured over 90 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
AID178387Effective dose for drug discrimination assay in rats using (+)-Amphitamine as training drug; NS = No substitution1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA).
AID1130886Induction of hyperactivity in Swiss Webster mouse assessed as sniffing at 0.025 to 0.3 mmol/kg, ip up to 90 mins1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
AID6406Affinity against 5-hydroxytryptamine receptors in rat fundus model1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Serotonin receptor affinities of psychoactive phenalkylamine analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (4,365)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901060 (24.28)18.7374
1990's857 (19.63)18.2507
2000's959 (21.97)29.6817
2010's1054 (24.15)24.3611
2020's435 (9.97)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 51.65

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index51.65 (24.57)
Research Supply Index8.49 (2.92)
Research Growth Index4.61 (4.65)
Search Engine Demand Index91.05 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (51.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials77 (1.60%)5.53%
Reviews303 (6.30%)6.00%
Case Studies414 (8.61%)4.05%
Observational2 (0.04%)0.25%
Other4,010 (83.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Effects of MDMA-like Substances in Healthy Subjects [NCT04847206]Phase 124 participants (Anticipated)Interventional2021-12-01Recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]