Page last updated: 2024-11-05

n,n-dimethyltryptamine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

N,N-Dimethyltryptamine: An N-methylated indoleamine derivative and serotonergic hallucinogen which occurs naturally and ubiquitously in several plant species including Psychotria veridis. It also occurs in trace amounts in mammalian brain, blood, and urine, and is known to act as an agonist or antagonist of certain SEROTONIN RECEPTORS. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

N,N-dimethyltryptamine : A tryptamine derivative having two N-methyl substituents on the side-chain. [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]

Cross-References

ID SourceID
PubMed CID6089
CHEMBL ID12420
CHEBI ID28969
SCHEMBL ID335710
MeSH IDM0006467

Synonyms (70)

Synonym
AKOS005446117
gtpl141
(2-indol-3-ylethyl)dimethylamine
2-(1h-indol-3-yl)-n,n-dimethyl-ethanamine
dmt (psychogenic)
indole, 3-(2-(dimethylamino)ethyl)-
einecs 200-508-4
nsc 63795
dea no. 7435
brn 0138259
indole, 3-[2-(dimethylamino)ethyl]-
3-(2-dimethylaminoethyl)indole
dimethyltryptamine
wln: t56 bmj d2n1&1
nsc-63795
2-(3-indolyl)ethyldimethylamine
nsc63795
2-(1h-indol-3-yl)-n,n-dimethylethanamine
inchi=1/c12h16n2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13h,7-8h2,1-2h
1h-indole-3-ethanamine, n,n-dimethyl-
STK370594
61-50-7
n,n-dimethyltryptamine
C08302
DMT ,
3-[2-(dimethylamino)ethyl]indole
n,n-dimethyl-1h-indole-3-ethylamine
DB01488
CHEBI:28969 ,
n,n-dimethyltryptamine, free base
D-5500
n,n dimethyltryptamine
L001288
CHEMBL12420 ,
bdbm50026868
2-(1h-indol-3-yl)-ethyl-dimethyl-amine
(psychogenic)
unii-wub601bhaa
hsdb 8017
wub601bhaa ,
SCHEMBL335710
MB00483
[2-(1h-indol-3-yl)-ethyl]-dimethyl-amine
1h-indole-3-ethanamine,n,n-dimethyl
3-(2-dimethylaminoethyl) indole
3-(2-(dimethylamino)ethyl)indole
n,n-dimethyl-1h-indole-3-ethanamine
n-dimethyltryptamine
n,n-dimethyltryptamine [mi]
dimethyltryptamine [who-dd]
dimethyltryptamine [mart.]
2-(1h-indol-3-yl)-n,n-dimethylethanamine #
2-(1h-indol-3-yl)-n,n-dimethylethylamine
3-(dimethylaminoethyl)-indole
DTXSID60110053 ,
[2-(1h-indol-3-yl)ethyl]dimethylamine
n,n-dimethyl-1h-indole-3-ethanamine (9ci)
2-(1h-indol-3-yl)-n,n-dimethylethanamine (acd/name 4.0)
n-(2-(1h-indol-3-yl)ethyl)-n,n-dimethylamine (acd/name 4.0)
3-(2-(dimethylamino)ethyl)-indole
3-[2- (dimethylamino)ethyl]-indole
nn-dimethyltryptamine
n,n-dimethyltryptamine, >=97% (hplc)
Q407217
AS-47089
dimethyltryptamine(dmt)
(n,n)-dimethyltryptamine
dtxcid4065313
dimethyltryptamine (mart.)
n,n-dimethyltryptamine, 1mg/ml in methanol

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Adverse events were mostly mild with one self-limited serious event."( Exploratory study of the dose-related safety, tolerability, and efficacy of dimethyltryptamine (DMT) in healthy volunteers and major depressive disorder.
Cozzi, NV; D'Souza, DC; Flynn, LT; Ranganathan, M; Safi-Aghdam, H; Syed, SA, 2022
)
0.72

Pharmacokinetics

ExcerptReferenceRelevance
" Dosing regimens were calculated based on pharmacokinetic modelling and predictions with progression to each subsequent dose level contingent upon safety and tolerability."( Pharmacokinetics of N,N-dimethyltryptamine in Humans.
Allen, G; Benway, T; Bowman, A; Erritzoe, D; Good, M; Hughes, C; James, E; Joel, Z; Routledge, C; Timmermann, C; Topping, H; Weaver, R, 2023
)
1.23
" DMT was rapidly cleared for all doses: mean elimination half-life was 9-12 min."( Pharmacokinetics of N,N-dimethyltryptamine in Humans.
Allen, G; Benway, T; Bowman, A; Erritzoe, D; Good, M; Hughes, C; James, E; Joel, Z; Routledge, C; Timmermann, C; Topping, H; Weaver, R, 2023
)
1.23

Bioavailability

ExcerptReferenceRelevance
" In contrast, the recreational use of N,N-dimethyltryptamine involves consumption mainly by smoking or inhalation, both of which markedly increase its bioavailability and the potential for intoxications."( Ritualistic Use of Ayahuasca versus Street Use of Similar Substances Seized by the Police: A Key Factor Involved in the Potential for Intoxications and Overdose?
Calemi, DB; Cazenave, Sde O; Costa, JL; Lanaro, R; Linardi, A; Togni, LR; Yonamine, M,
)
0.4

Dosage Studied

N,N-dimethyltryptamine (DMT) showed a clear dose-response relationship in the stimulation of the release of prolactin.

ExcerptRelevanceReference
" The dose-response curves for the phenethylamine hallucinogens were shifted significantly to the right and to a greater degree than were those for the indolealkylamine hallucinogens."( The 5HT2 antagonist pirenperone reverses disruption of FR-40 by hallucinogenic drugs.
Mokler, DJ; Rech, RH; Stoudt, KW, 1985
)
0.27
" N,N-dimethyltryptamine showed a clear dose-response relationship in the stimulation of the release of prolactin."( Indolealkylamines and prolactin secretion. A structure-activity study in the central nervous system of the rat.
Brown, GM; Seeman, G, 1985
)
1.18
" In the present study we determined the time-course and dose-response effects of 6-MeO-THbetaC for blockade of AGS."( Effects of 6-methoxy-1,2,3,4-tetrahydro-beta-carboline (6-MeO-THbetaC) on audiogenic seizures in DBA/2J mice.
Buckholtz, NS; Sparks, DL, 1980
)
0.26
" Furthermore, combinations of the hallucinogens interact with potentiation to cause FR-40 pausing, whereas a variety of non-hallucinogenic psychoactive drugs failed to shift the dose-response patterns of pausing for DOM or LSD."( Neurotransmitter basis of the behavioral effects of hallucinogens.
Commissaris, RL; Rech, RH, 1982
)
0.26
"To begin applying basic neuropharmacological hypotheses of hallucinogenic drug actions to humans, we generated dose-response data for intravenously administered dimethyltryptamine fumarate's (DMT) neuroendocrine, cardiovascular, autonomic, and subjective effects in a group of experienced hallucinogen users."( Dose-response study of N,N-dimethyltryptamine in humans. I. Neuroendocrine, autonomic, and cardiovascular effects.
Qualls, CR; Strassman, RJ, 1994
)
0.6
"Dimethyltryptamine can be administered safely to experienced hallucinogen users and dose-response data generated for several measures hypothesized under serotonergic modulatory control."( Dose-response study of N,N-dimethyltryptamine in humans. I. Neuroendocrine, autonomic, and cardiovascular effects.
Qualls, CR; Strassman, RJ, 1994
)
0.6
"We generated dose-response data for the endogenous and ultra-short-acting hallucinogen, N,N-dimethyltryptamine (DMT), in a cohort of experienced hallucinogen users, measuring multiple biological and psychological outcome measures."( Human psychopharmacology of N,N-dimethyltryptamine.
Strassman, RJ, 1996
)
0.81
", fast and slow metabolizers of harmine-in 14 experienced male members of the UniĆ£o do Vegetal (UDV) who received a standardized dosage of hoasca."( Fast and slow metabolizers of Hoasca.
Callaway, JC, 2005
)
0.33
" For caffeine and scopolamine, even the lowest dosage tested (5 mg/horse/day and 2 mg/horse/day respectively) induced detectable concentrations of the molecule in urine."( Urinary excretion of dietary contaminants in horses.
Bonnaire, Y; Julliand, V; Lallemand, A; Respondek, F, 2006
)
0.33
" To date, only one clinical trial has been published on 5-MeO-DMT, demonstrating the safety of vaporized dosing up to 18 mg."( The clinical pharmacology and potential therapeutic applications of 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).
Davis, AK; Lancelotta, R; Mason, NL; Ramaekers, JG; Reckweg, JT; Szabo, A; Uthaug, MV, 2022
)
0.95
" Tolerability, safety, cardiovascular function, abuse liability, psychedelic, and psychotomimetic effects, mood, and anxiety were assessed at each dosing session."( Exploratory study of the dose-related safety, tolerability, and efficacy of dimethyltryptamine (DMT) in healthy volunteers and major depressive disorder.
Cozzi, NV; D'Souza, DC; Flynn, LT; Ranganathan, M; Safi-Aghdam, H; Syed, SA, 2022
)
0.72
" In addition, this article considers the effects that macro- and microdoses have on behavior and psychopathology in light of their dosage characteristics and contexts of use."( Macrodosing to microdosing with psychedelics: Clinical, social, and cultural perspectives.
Kaypak, AC; Raz, A, 2022
)
0.72
" Dosing regimens were calculated based on pharmacokinetic modelling and predictions with progression to each subsequent dose level contingent upon safety and tolerability."( Pharmacokinetics of N,N-dimethyltryptamine in Humans.
Allen, G; Benway, T; Bowman, A; Erritzoe, D; Good, M; Hughes, C; James, E; Joel, Z; Routledge, C; Timmermann, C; Topping, H; Weaver, R, 2023
)
1.23
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
tryptaminesTryptamine and its substitution derivatives.
tryptamine alkaloid
[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]

Pathways (1)

PathwayProteinsCompounds
Melatonin metabolism and effects016

Protein Targets (35)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Ki100.00000.00020.656110.0000AID40666
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki1.63600.00010.601710.0000AID385348
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Ki100.00000.00020.656110.0000AID40666
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Ki100.00000.00020.656110.0000AID40666
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Ki100.00000.00020.561410.0000AID40666
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Ki0.25900.00010.739610.0000AID4069
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Ki100.00000.00020.635210.0000AID40666
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Ki100.00000.00020.621710.0000AID40666
AcetylcholinesteraseHomo sapiens (human)Ki0.06500.00001.27869.7300AID3191
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Ki100.00000.00020.675810.0000AID40666
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Ki100.00000.00020.646910.0000AID40666
5-hydroxytryptamine receptor 2AHomo sapiens (human)Ki0.06500.00000.385510.0000AID3191
5-hydroxytryptamine receptor 2CHomo sapiens (human)Ki0.03300.00010.954910.0000AID5621
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Ki100.00000.00020.656110.0000AID40666
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Ki100.00000.00020.656110.0000AID40666
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Ki100.00000.00020.671210.0000AID40666
5-hydroxytryptamine receptor 2BHomo sapiens (human)Ki0.10100.00030.769310.0000AID5767
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Ki100.00000.00020.557710.0000AID40666
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Ki100.00000.00020.640310.0000AID40666
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Ki100.00000.00020.570810.0000AID40666
Sigma non-opioid intracellular receptor 1Cavia porcellus (domestic guinea pig)Ki15.00000.00000.338510.0000AID598495
GABA theta subunitRattus norvegicus (Norway rat)Ki100.00000.00020.656110.0000AID40666
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Ki100.00000.00020.656110.0000AID40666
[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)Kd1.00000.00042.58328.5114AID6412
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Kd1.00000.00012.62198.5114AID6412
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Kd1.00000.00012.29338.5114AID6412
5-hydroxytryptamine receptor 2AHomo sapiens (human)EC50 (µMol)0.02220.00000.22763.4750AID1782619; AID1815952
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Kd1.00000.02342.74218.5114AID6412
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Kd1.00000.02342.74218.5114AID6412
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Kd1.00000.02342.74218.5114AID6412
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Kd1.00000.00042.47358.5114AID5817; AID6412
5-hydroxytryptamine receptor 6Rattus norvegicus (Norway rat)Kd1.00000.02342.74218.5114AID6412
5-hydroxytryptamine receptor 7 Rattus norvegicus (Norway rat)Kd1.00000.00012.70068.5114AID6412
5-hydroxytryptamine receptor 5ARattus norvegicus (Norway rat)Kd1.00000.02342.74218.5114AID6412
5-hydroxytryptamine receptor 5BRattus norvegicus (Norway rat)Kd1.00000.02342.74218.5114AID6412
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)Kd1.00000.00082.62148.5114AID6412
5-hydroxytryptamine receptor 4 Rattus norvegicus (Norway rat)Kd1.00000.02342.74218.5114AID6412
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)Kd1.00000.00082.62148.5114AID6412
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (86)

Processvia Protein(s)Taxonomy
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
temperature homeostasis5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of cytokine production involved in immune response5-hydroxytryptamine receptor 2AHomo sapiens (human)
glycolytic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
intracellular calcium ion homeostasis5-hydroxytryptamine receptor 2AHomo sapiens (human)
activation of phospholipase C activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of cytosolic calcium ion concentration5-hydroxytryptamine receptor 2AHomo sapiens (human)
memory5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of cell population proliferation5-hydroxytryptamine receptor 2AHomo sapiens (human)
response to xenobiotic stimulus5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of phosphatidylinositol biosynthetic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
regulation of dopamine secretion5-hydroxytryptamine receptor 2AHomo sapiens (human)
artery smooth muscle contraction5-hydroxytryptamine receptor 2AHomo sapiens (human)
urinary bladder smooth muscle contraction5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of heat generation5-hydroxytryptamine receptor 2AHomo sapiens (human)
negative regulation of potassium ion transport5-hydroxytryptamine receptor 2AHomo sapiens (human)
phosphatidylinositol 3-kinase/protein kinase B signal transduction5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of neuron apoptotic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
protein localization to cytoskeleton5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of fat cell differentiation5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of glycolytic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of vasoconstriction5-hydroxytryptamine receptor 2AHomo sapiens (human)
symbiont entry into host cell5-hydroxytryptamine receptor 2AHomo sapiens (human)
sensitization5-hydroxytryptamine receptor 2AHomo sapiens (human)
behavioral response to cocaine5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of inflammatory response5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylation5-hydroxytryptamine receptor 2AHomo sapiens (human)
detection of temperature stimulus involved in sensory perception of pain5-hydroxytryptamine receptor 2AHomo sapiens (human)
detection of mechanical stimulus involved in sensory perception of pain5-hydroxytryptamine receptor 2AHomo sapiens (human)
release of sequestered calcium ion into cytosol5-hydroxytryptamine receptor 2AHomo sapiens (human)
negative regulation of synaptic transmission, glutamatergic5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascade5-hydroxytryptamine receptor 2AHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathway5-hydroxytryptamine receptor 2AHomo sapiens (human)
presynaptic modulation of chemical synaptic transmission5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of execution phase of apoptosis5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of platelet aggregation5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of DNA biosynthetic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 2AHomo sapiens (human)
phospholipase C-activating serotonin receptor signaling pathway5-hydroxytryptamine receptor 2AHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 2AHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 2AHomo sapiens (human)
behavioral fear response5-hydroxytryptamine receptor 2CHomo sapiens (human)
intracellular calcium ion homeostasis5-hydroxytryptamine receptor 2CHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 2CHomo sapiens (human)
phospholipase C-activating serotonin receptor signaling pathway5-hydroxytryptamine receptor 2CHomo sapiens (human)
locomotory behavior5-hydroxytryptamine receptor 2CHomo sapiens (human)
feeding behavior5-hydroxytryptamine receptor 2CHomo sapiens (human)
positive regulation of phosphatidylinositol biosynthetic process5-hydroxytryptamine receptor 2CHomo sapiens (human)
cGMP-mediated signaling5-hydroxytryptamine receptor 2CHomo sapiens (human)
regulation of nervous system process5-hydroxytryptamine receptor 2CHomo sapiens (human)
regulation of appetite5-hydroxytryptamine receptor 2CHomo sapiens (human)
regulation of corticotropin-releasing hormone secretion5-hydroxytryptamine receptor 2CHomo sapiens (human)
positive regulation of fat cell differentiation5-hydroxytryptamine receptor 2CHomo sapiens (human)
positive regulation of calcium-mediated signaling5-hydroxytryptamine receptor 2CHomo sapiens (human)
release of sequestered calcium ion into cytosol5-hydroxytryptamine receptor 2CHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascade5-hydroxytryptamine receptor 2CHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathway5-hydroxytryptamine receptor 2CHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 2CHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 2CHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 2CHomo sapiens (human)
neural crest cell migration5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of cytokine production5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of endothelial cell proliferation5-hydroxytryptamine receptor 2BHomo sapiens (human)
G protein-coupled receptor internalization5-hydroxytryptamine receptor 2BHomo sapiens (human)
heart morphogenesis5-hydroxytryptamine receptor 2BHomo sapiens (human)
cardiac muscle hypertrophy5-hydroxytryptamine receptor 2BHomo sapiens (human)
intracellular calcium ion homeostasis5-hydroxytryptamine receptor 2BHomo sapiens (human)
G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 2BHomo sapiens (human)
activation of phospholipase C activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 2BHomo sapiens (human)
phospholipase C-activating serotonin receptor signaling pathway5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of cell population proliferation5-hydroxytryptamine receptor 2BHomo sapiens (human)
response to xenobiotic stimulus5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of phosphatidylinositol biosynthetic process5-hydroxytryptamine receptor 2BHomo sapiens (human)
neural crest cell differentiation5-hydroxytryptamine receptor 2BHomo sapiens (human)
intestine smooth muscle contraction5-hydroxytryptamine receptor 2BHomo sapiens (human)
phosphorylation5-hydroxytryptamine receptor 2BHomo sapiens (human)
calcium-mediated signaling5-hydroxytryptamine receptor 2BHomo sapiens (human)
cGMP-mediated signaling5-hydroxytryptamine receptor 2BHomo sapiens (human)
vasoconstriction5-hydroxytryptamine receptor 2BHomo sapiens (human)
negative regulation of apoptotic process5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of canonical NF-kappaB signal transduction5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of MAP kinase activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
phosphatidylinositol 3-kinase/protein kinase B signal transduction5-hydroxytryptamine receptor 2BHomo sapiens (human)
embryonic morphogenesis5-hydroxytryptamine receptor 2BHomo sapiens (human)
regulation of behavior5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of nitric-oxide synthase activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
release of sequestered calcium ion into cytosol5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of cell division5-hydroxytryptamine receptor 2BHomo sapiens (human)
ERK1 and ERK2 cascade5-hydroxytryptamine receptor 2BHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascade5-hydroxytryptamine receptor 2BHomo sapiens (human)
protein kinase C signaling5-hydroxytryptamine receptor 2BHomo sapiens (human)
cellular response to temperature stimulus5-hydroxytryptamine receptor 2BHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathway5-hydroxytryptamine receptor 2BHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 2BHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 2BHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 2BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (21)

Processvia Protein(s)Taxonomy
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
Gq/11-coupled serotonin receptor activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
virus receptor activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
protein tyrosine kinase activator activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
identical protein binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
protein-containing complex binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
Gq/11-coupled serotonin receptor activity5-hydroxytryptamine receptor 2CHomo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 2CHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 2CHomo sapiens (human)
identical protein binding5-hydroxytryptamine receptor 2CHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 2CHomo sapiens (human)
1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding5-hydroxytryptamine receptor 2CHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 2CHomo sapiens (human)
Gq/11-coupled serotonin receptor activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
G-protein alpha-subunit binding5-hydroxytryptamine receptor 2BHomo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
GTPase activator activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 2BHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 2BHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 2BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (27)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
neurofilament5-hydroxytryptamine receptor 2AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2AHomo sapiens (human)
caveola5-hydroxytryptamine receptor 2AHomo sapiens (human)
axon5-hydroxytryptamine receptor 2AHomo sapiens (human)
cytoplasmic vesicle5-hydroxytryptamine receptor 2AHomo sapiens (human)
presynaptic membrane5-hydroxytryptamine receptor 2AHomo sapiens (human)
neuronal cell body5-hydroxytryptamine receptor 2AHomo sapiens (human)
dendritic shaft5-hydroxytryptamine receptor 2AHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 2AHomo sapiens (human)
cell body fiber5-hydroxytryptamine receptor 2AHomo sapiens (human)
glutamatergic synapse5-hydroxytryptamine receptor 2AHomo sapiens (human)
G protein-coupled serotonin receptor complex5-hydroxytryptamine receptor 2AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2AHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 2AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2CHomo sapiens (human)
synapse5-hydroxytryptamine receptor 2CHomo sapiens (human)
G protein-coupled serotonin receptor complex5-hydroxytryptamine receptor 2CHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2CHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 2CHomo sapiens (human)
nucleoplasm5-hydroxytryptamine receptor 2BHomo sapiens (human)
cytoplasm5-hydroxytryptamine receptor 2BHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2BHomo sapiens (human)
synapse5-hydroxytryptamine receptor 2BHomo sapiens (human)
G protein-coupled serotonin receptor complex5-hydroxytryptamine receptor 2BHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 2BHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2BHomo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (52)

Assay IDTitleYearJournalArticle
AID1871167Intrinsic clearance in human hepatocytes assessed per 10^6 cells2022ACS medicinal chemistry letters, Sep-08, Volume: 13, Issue:9
Application of Deuterated
AID3192Efficacy against 5-hydroxytryptamine 2A receptor1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID1815948Stability in human liver mitochondria assessed as intrinsic clearance in presence of MAO-A and MAO-B2022ACS medicinal chemistry letters, Apr-14, Volume: 13, Issue:4
Improved Metabolically Stable 5-HT Receptor Modulators and the Development of New Antidepressants.
AID192229Percentage of animals emitting >80% of lever presses in rats at 4.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID1815951Stability in rat brain homogenate assessed as half life2022ACS medicinal chemistry letters, Apr-14, Volume: 13, Issue:4
Improved Metabolically Stable 5-HT Receptor Modulators and the Development of New Antidepressants.
AID385350Agonist activity at Sprague-Dawley rat 5HT2A receptor by drug discrimination assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands.
AID598201Selectivity index, ratio of CC50 for human HepG2.2.15 cells to IC50 for Hepatitis B virus2011Bioorganic & medicinal chemistry, May-15, Volume: 19, Issue:10
Tryptamine derivatives as novel non-nucleosidic inhibitors against hepatitis B virus.
AID598200Cytotoxicity against human HepG2(2.2.15) cells after 8 days by MTT assay2011Bioorganic & medicinal chemistry, May-15, Volume: 19, Issue:10
Tryptamine derivatives as novel non-nucleosidic inhibitors against hepatitis B virus.
AID6412Compound was evaluated for binding affinity towards 5-hydroxytryptamine receptor in isolated rat fundus preparation measured as pA21980Journal of medicinal chemistry, Nov, Volume: 23, Issue:11
Studies on several 7-substituted N,N-dimethyltryptamines.
AID1583472Induction of dendritogenesis in Sprague-Dawley rat cortical neurons assessed as increase in dendritic arbor complex at 1 nM after 1 hr supplemented with fresh neurobasal medium measured after 71 hrs by Alexa Fluor 488 dye based imaging analysis2020Journal of medicinal chemistry, 02-13, Volume: 63, Issue:3
Identification of Psychoplastogenic
AID1583471Induction of dendritogenesis in Sprague-Dawley rat cortical neurons assessed as dendritic arbor complexity at 10 uM after 1 hr supplemented with fresh neurobasal medium measured after 71 hrs by Alexa Fluor 488 dye based imaging analysis2020Journal of medicinal chemistry, 02-13, Volume: 63, Issue:3
Identification of Psychoplastogenic
AID40666In vitro inhibition of [3H]diazepam binding to benzodiazepine receptor in rat cerebral cortical membrane1982Journal of medicinal chemistry, Sep, Volume: 25, Issue:9
Beta-carbolines: synthesis and neurochemical and pharmacological actions on brain benzodiazepine receptors.
AID1062232Displacement of [3H]-(+)-pentazocine from sigma 1 receptor in rat liver homogenates2013Journal of medicinal chemistry, Dec-27, Volume: 56, Issue:24
Structure of the Ļƒ1 receptor and its ligand binding site.
AID5621Compound was tested for the displacement of [125I]DOI from cloned human 5-hydroxytryptamine 2C receptor1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID1782619Agonist activity at 5HT2A receptor (unknown origin) expressed in HEK293 cells by FLIPR calcium flux assay2021ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12
The Psychedelic Renaissance: Addressing Potential Adverse Effects in a Therapeutic Setting.
AID1871169Half life in human hepatocytes2022ACS medicinal chemistry letters, Sep-08, Volume: 13, Issue:9
Application of Deuterated
AID174853Drug Discrimination in LY-263284 trained rats at 1.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID192064Drug Discrimination in LY-263284 trained rats at 8.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID175230Percentage of animals failing to emit 50 lever presses within 15 min in rats at 4.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID174852Drug Discrimination in LY-263284 trained rats at 0.5 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID3191Compound was tested for the displacement of [125I]DOI from clone human 5-hydroxytryptamine 2A receptor1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID1815950Stability in rat brain homogenate assessed as compound remaining measured after 120 mins2022ACS medicinal chemistry letters, Apr-14, Volume: 13, Issue:4
Improved Metabolically Stable 5-HT Receptor Modulators and the Development of New Antidepressants.
AID175231Percentage of animals failing to emit 50 lever presses within 15 min in rats at 8.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID174854Drug Discrimination in LY-263284 trained rats at 2.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID192063Drug Discrimination in LY-263284 trained rats at 4.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID192230Percentage of animals emitting >80% of lever presses in rats at 8.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID5767Compound was tested for the displacement of [3H]5-HT from clone human 5-hydroxytryptamine 2B receptor1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID385349Lipophilicity of compound by immobilized artificial membrane column containing phosphatidylcholine head groups HPLC2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands.
AID385348Displacement of [3H]MDL100907 from 5HT2A receptor in Sprague-Dawley rat brain by liquid scintillation spectroscopy2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands.
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.
AID192060Drug Discrimination in LY-263284 trained rats at 0.5 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID174855Drug Discrimination in LY-263284 trained rats at 4.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID197150The ability to inhibit the 5-HT-induced contraction of isolated rat fundus muscle was determined1982Journal of medicinal chemistry, Nov, Volume: 25, Issue:11
Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives.
AID174856Drug Discrimination in LY-263284 trained rats at 8.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID1782621Agonist activity at 5HT2A receptor (unknown origin) expressed in HEK293 cells assessed as maximal effect by FLIPR calcium flux assay relative to control2021ACS medicinal chemistry letters, Dec-09, Volume: 12, Issue:12
The Psychedelic Renaissance: Addressing Potential Adverse Effects in a Therapeutic Setting.
AID4069Compound was tested for the displacement of [3H]-8-OH- DPAT from rat brain 5-hydroxytryptamine 1A receptor1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID1815949Stability in human liver mitochondria assessed as compound remaining in presence of MAO-A and MAO-B measured after 60 mins2022ACS medicinal chemistry letters, Apr-14, Volume: 13, Issue:4
Improved Metabolically Stable 5-HT Receptor Modulators and the Development of New Antidepressants.
AID175228Percentage of animals failing to emit 50 lever presses within 15 min in rats at 1.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID192062Drug Discrimination in LY-263284 trained rats at 2.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID598199Antiviral activity against Hepatitis B virus infected in human HepG2(2.2.15) cells assessed as inhibition of viral DNA replication after 4 days by RT-PCR analysis2011Bioorganic & medicinal chemistry, May-15, Volume: 19, Issue:10
Tryptamine derivatives as novel non-nucleosidic inhibitors against hepatitis B virus.
AID192061Drug Discrimination in LY-263284 trained rats at 1.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID175229Percentage of animals failing to emit 50 lever presses within 15 min in rats at 2.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID1815952Agonist activity at 5-HT2A receptor (unknown origin) by calcium flux assay2022ACS medicinal chemistry letters, Apr-14, Volume: 13, Issue:4
Improved Metabolically Stable 5-HT Receptor Modulators and the Development of New Antidepressants.
AID192227Percentage of animals emitting >80% of lever presses in rats at 1.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID192228Percentage of animals emitting >80% of lever presses in rats at 2.0 mg/kg dose1999Journal of medicinal chemistry, Mar-25, Volume: 42, Issue:6
Thieno[3,2-b]- and thieno[2,3-b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N-dimethyltryptamine.
AID1131175Antagonist activity at 5-HT1 receptor in Sprague-Dawley rat assessed as inhibition of 5-HT-induced stomach fundus contraction1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Bufotenine esters.
AID5817The binding affinity to 5-hydroxytryptamine 2B receptor of rat fundus1982Journal of medicinal chemistry, Jan, Volume: 25, Issue:1
2,3-dihydro and carbocyclic analogues of tryptamines: interaction with serotonin receptors.
AID1815947Stability in human liver mitochondria assessed as half life in presence of MAO-A and MAO-B2022ACS medicinal chemistry letters, Apr-14, Volume: 13, Issue:4
Improved Metabolically Stable 5-HT Receptor Modulators and the Development of New Antidepressants.
AID598495Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain by scintillation analyzer2011Bioorganic & medicinal chemistry, May-15, Volume: 19, Issue:10
Design, synthesis and pharmacological evaluation of spirocyclic Ļƒ(1) receptor ligands with exocyclic amino moiety (increased distance 1).
AID1131176Chloroform to aqueous buffer partition coefficient, log P of the compound at pH 7.4 by shake flask method1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Bufotenine esters.
AID1345170Human 5-HT6 receptor (5-Hydroxytryptamine receptors)1996Journal of neurochemistry, Jan, Volume: 66, Issue:1
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.
AID1346528Human 5-HT1D receptor (5-Hydroxytryptamine receptors)1996Molecular pharmacology, Dec, Volume: 50, Issue:6
Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamin
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (416)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990222 (53.37)18.7374
1990's23 (5.53)18.2507
2000's47 (11.30)29.6817
2010's61 (14.66)24.3611
2020's63 (15.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 38.41

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index38.41 (24.57)
Research Supply Index6.17 (2.92)
Research Growth Index4.81 (4.65)
Search Engine Demand Index59.54 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (38.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials29 (6.46%)5.53%
Reviews45 (10.02%)6.00%
Case Studies8 (1.78%)4.05%
Observational2 (0.45%)0.25%
Other365 (81.29%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (30)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Effects of Dimethyltryptamine (DMT) in Healthy Subjects: A Placebo-controlled Cross-over Study [NCT04353024]Phase 131 participants (Actual)Interventional2021-06-18Completed
The Potential Therapeutic Effects of Psychedelic, N, N-dimethyltryptamine (DMT), on Alcohol Use Disorder (AUD) [NCT06070649]Phase 163 participants (Anticipated)Interventional2024-01-17Not yet recruiting
Acute Dose-dependent Effects of DMT-bolus Applications in Healthy Subjects: A Placebo-controlled Cross-over Study (DMT BDR-Study). [NCT05695495]Phase 136 participants (Anticipated)Interventional2024-03-15Not yet recruiting
Acute Dose-dependent Effects of DMT in Healthy Subjects: A Placebo-controlled Cross-over Study [NCT05384678]Phase 124 participants (Anticipated)Interventional2022-11-15Recruiting
A Randomized, Double-blind, Placebo-controlled, Phase 2b Trial With an Open-label Extension to Determine the Safety and Efficacy of GH001 in Patients With Treatment-resistant Depression [NCT05800860]Phase 280 participants (Anticipated)Interventional2023-05-24Recruiting
Effects of Psilocybin on Behavior, Psychology and Brain Function in Long-term Meditators [NCT02145091]Phase 140 participants (Actual)Interventional2014-05-31Completed
An Open Label Trial of Inhaled N,N-Dimethyltryptamine in Patients With Partial Response in Depression. [NCT06094907]Phase 212 participants (Anticipated)Interventional2023-10-09Recruiting
Psilocybin Treatment of Major Depressive Disorder With Co-occurring Alcohol Use Disorder [NCT04620759]Phase 290 participants (Anticipated)Interventional2021-04-14Recruiting
An Open-Label Pilot Study Examining the Feasibility, Safety, and Effectiveness of Psilocybin Therapy for Depression in Bipolar II Disorder [NCT05065294]Phase 214 participants (Anticipated)Interventional2022-01-28Recruiting
Inhaled N, N-Dimethyltryptamine: a Phase I Study in Healthy Adults [NCT05573568]Phase 127 participants (Actual)Interventional2022-06-01Completed
A Double-blind, Randomised, Placebo-controlled Study to Evaluate the Pharmacokinetics, Safety and Pharmacodynamics of Ascending Single and Fixed Repeat Intravenous Doses of DMT in Healthy Subjects [NCT05559931]Phase 160 participants (Anticipated)Interventional2023-01-13Recruiting
A Phase 2 Clinical Trial of GH001 in Patients With Postpartum Depression [NCT05804708]Phase 215 participants (Anticipated)Interventional2023-03-02Recruiting
A Phase 2 Clinical Trial of GH001 in Patients With Bipolar II Disorder and a Current Major Depressive Episode [NCT05839509]Phase 215 participants (Anticipated)Interventional2023-04-06Recruiting
Psychopharmacology of Psilocybin in Cancer Patients [NCT00465595]Phase 256 participants (Actual)Interventional2007-04-30Completed
A Double-blind, Randomized Trial Examining the Preliminary Efficacy of Psilocybin Therapy for People With Chronic Low Back Pain [NCT05351541]Phase 1/Phase 230 participants (Anticipated)Interventional2023-12-01Recruiting
Psilocybin-assisted Group Therapy for Demoralization in Long-term AIDS Survivors [NCT02950467]Phase 130 participants (Actual)Interventional2018-01-05Completed
Effects of Psilocybin on Anxiety and Psychosocial Distress in Cancer Patients [NCT00957359]Early Phase 129 participants (Actual)Interventional2009-02-28Completed
Psilocybin in Patients With Fibromyalgia: EEG-measured Brain Biomarkers of Action [NCT05548075]20 participants (Anticipated)Observational2022-08-15Recruiting
A Double-blind, Randomised, Placebo-controlled Study of Intravenous Doses of SPL026 (DMT Fumarate), a Serotonergic Psychedelic, in Healthy Subjects (Part A) and Patients With Major Depressive Disorder (Part B) [NCT04673383]Phase 1/Phase 266 participants (Actual)Interventional2021-02-04Completed
Psilocybin-facilitated Smoking Cessation Treatment: A Pilot Study [NCT01943994]95 participants (Anticipated)Interventional2008-09-30Active, not recruiting
Fixed Order, Open-Label, Dose-Escalation Study of DMT in Humans [NCT04711915]Phase 130 participants (Anticipated)Interventional2021-03-17Active, not recruiting
Effects of Psilocybin on Electrophysiology and the Dynamic Content of Thought [NCT05301608]Phase 1/Phase 230 participants (Anticipated)Interventional2022-03-03Recruiting
Psilocybin Therapy for Depression and Anxiety in Parkinson's Disease: a Pilot Study [NCT04932434]Phase 210 participants (Anticipated)Interventional2021-08-15Active, not recruiting
A Phase 1/2 Study of GH001 in Patients With Treatment-Resistant Depression [NCT04698603]Phase 1/Phase 216 participants (Actual)Interventional2019-11-12Completed
A Phase 1 Dose-ranging Study of GH001 in Healthy Volunteers [NCT04640831]Phase 122 participants (Actual)Interventional2019-03-13Completed
A Phase 1 Clinical Trial to Determine the Safety, Pharmacokinetics and Pharmacodynamics of Intravenous GH002 in Healthy Volunteers [NCT05753956]Phase 164 participants (Anticipated)Interventional2022-12-22Recruiting
An Open-Label Study Investigating the Safety, Tolerability, Pharmacokinetics, Pharmacodynamics & Exploratory Efficacy of Intravenous SPL026 Drug Product (DMT Fumarate) Alone or in Combination With SSRIs in Patients With Major Depressive Disorder [NCT05553691]Phase 118 participants (Actual)Interventional2022-12-13Completed
Inhaled N,N-Dimethyltryptamine: a Safety and Tolerability Study in Healthy Adults [NCT05901012]Phase 125 participants (Actual)Interventional2023-04-26Completed
A Phase 1 Study to Determine the Pharmacokinetics and Pharmacodynamics of Single and Multiple Inhaled Doses of GH001 in Healthy Volunteers [NCT05163691]Phase 146 participants (Actual)Interventional2021-06-21Completed
A Phase 1, First-in-human, Double-blind, Placebo-controlled, Randomized, Single- and Multiple-ascending-dose Study to Determine the Safety, Tolerability, and Pharmacokinetics of 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) Administered by Intramuscular In [NCT05698095]Phase 154 participants (Actual)Interventional2022-12-27Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT00465595 (2) [back to overview]GRID-HAM-D-17 -- Structured Interview Guide for the Hamilton Depression Scale.
NCT00465595 (2) [back to overview]HAM-A Assessed With the SIGH-A -- a Structured Interview Guide for the Hamilton Anxiety Rating Scale (SIGH-A).
NCT00957359 (54) [back to overview]QoL Physical Health Scale
NCT00957359 (54) [back to overview]QoL Physical Health Scale
NCT00957359 (54) [back to overview]QoL Physical Health Scale
NCT00957359 (54) [back to overview]QoL Psychological Scale
NCT00957359 (54) [back to overview]QoL Psychological Scale
NCT00957359 (54) [back to overview]QoL Psychological Scale
NCT00957359 (54) [back to overview]QoL Social Relationships Scale
NCT00957359 (54) [back to overview]QoL Social Relationships Scale
NCT00957359 (54) [back to overview]HADS Anxiety
NCT00957359 (54) [back to overview]QoL Social Relationships Scale
NCT00957359 (54) [back to overview]STAI State
NCT00957359 (54) [back to overview]STAI State
NCT00957359 (54) [back to overview]STAI State
NCT00957359 (54) [back to overview]STAI State
NCT00957359 (54) [back to overview]STAI State
NCT00957359 (54) [back to overview]STAI State
NCT00957359 (54) [back to overview]STAI Trait
NCT00957359 (54) [back to overview]STAI Trait
NCT00957359 (54) [back to overview]STAI Trait
NCT00957359 (54) [back to overview]STAI Trait
NCT00957359 (54) [back to overview]STAI Trait
NCT00957359 (54) [back to overview]STAI Trait
NCT00957359 (54) [back to overview]STAI Trait
NCT00957359 (54) [back to overview]STAI Trait
NCT00957359 (54) [back to overview]State-Trait Anxiety Inventory (STAI) State
NCT00957359 (54) [back to overview]Death Anxiety Scale
NCT00957359 (54) [back to overview]Death Anxiety Scale
NCT00957359 (54) [back to overview]Death Anxiety Scale
NCT00957359 (54) [back to overview]Death Transcendence Scale
NCT00957359 (54) [back to overview]Death Transcendence Scale
NCT00957359 (54) [back to overview]Demoralization Scale
NCT00957359 (54) [back to overview]Demoralization Scale
NCT00957359 (54) [back to overview]Demoralization Scale
NCT00957359 (54) [back to overview]HADS Anxiety
NCT00957359 (54) [back to overview]HADS Anxiety
NCT00957359 (54) [back to overview]HADS Anxiety
NCT00957359 (54) [back to overview]HADS Anxiety
NCT00957359 (54) [back to overview]HADS Anxiety
NCT00957359 (54) [back to overview]STAI State
NCT00957359 (54) [back to overview]HADS Anxiety
NCT00957359 (54) [back to overview]HADS Anxiety
NCT00957359 (54) [back to overview]HADS Depression
NCT00957359 (54) [back to overview]HADS Depression
NCT00957359 (54) [back to overview]HADS Depression
NCT00957359 (54) [back to overview]HADS Depression
NCT00957359 (54) [back to overview]HADS Depression
NCT00957359 (54) [back to overview]HADS Depression
NCT00957359 (54) [back to overview]HADS Depression
NCT00957359 (54) [back to overview]Hopelessness
NCT00957359 (54) [back to overview]Hopelessness
NCT00957359 (54) [back to overview]Hopelessness
NCT00957359 (54) [back to overview]QoL Environment Scale
NCT00957359 (54) [back to overview]QoL Environment Scale
NCT00957359 (54) [back to overview]QoL Environment Scale
NCT02950467 (25) [back to overview]Change From Baseline in Antiretroviral Medication Adherence Scale at 3-month Follow-up
NCT02950467 (25) [back to overview]Change From Baseline in Antiretroviral Medication Adherence Scale at End-of-treatment
NCT02950467 (25) [back to overview]Change From Baseline in Center for Epidemiologic Studies Depression Scale-Revised at 3-month Follow-up
NCT02950467 (25) [back to overview]Change From Baseline in Center for Epidemiologic Studies Depression Scale-Revised at End-of-treatment
NCT02950467 (25) [back to overview]Change From Baseline in Demoralization Scale-II at 3-month Follow-up
NCT02950467 (25) [back to overview]Change From Baseline in Demoralization Scale-II at End-of-treatment
NCT02950467 (25) [back to overview]Change From Baseline in Experiences in Closer Relationships-M16 (Anxiety) at 3-month Follow-up
NCT02950467 (25) [back to overview]Change From Baseline in Experiences in Closer Relationships-M16 (Anxiety) at End-of-treatment
NCT02950467 (25) [back to overview]Change From Baseline in Experiences in Closer Relationships-M16 (Avoidance) at End-of-treatment
NCT02950467 (25) [back to overview]Change From Baseline in HIV and Abuse Related Shame Inventory at 3-month Follow-up
NCT02950467 (25) [back to overview]Change From Baseline in HIV and Abuse Related Shame Inventory at End-of-treatment
NCT02950467 (25) [back to overview]Change From Baseline in Inventory of Complicated Grief at 3-month Follow-up
NCT02950467 (25) [back to overview]Change From Baseline in Inventory of Complicated Grief-Revised at End-of-treatment
NCT02950467 (25) [back to overview]Change From Baseline in McGill Quality of Life Questionnaire-Revised (Overall) at 3-month Follow-up
NCT02950467 (25) [back to overview]Change From Baseline in McGill Quality of Life Questionnaired-Revised (Overall) at End-of-treatment
NCT02950467 (25) [back to overview]Change From Baseline in PTSD Checklist 5 at 3-month Follow-up
NCT02950467 (25) [back to overview]Change From Baseline in PTSD Checklist 5 at End-of-treatment
NCT02950467 (25) [back to overview]Change From Baseline in State-Trait Anxiety Inventory (State) at 3-month Follow-up
NCT02950467 (25) [back to overview]Change From Baseline in State-Trait Anxiety Inventory (State) at End-of-treatment
NCT02950467 (25) [back to overview]Change From Baseline in State-Trait Anxiety Inventory (Trait) at 3-month Follow-up
NCT02950467 (25) [back to overview]Change From Baseline in State-Trait Anxiety Inventory (Trait) at End-of-treatment
NCT02950467 (25) [back to overview]Number of Participants Who Experienced Treatment-related Adverse Events as Assessed by NIH Division of AIDS Table for Grading the Severity of Adult and Pediatric Adverse Events, Version 2.0
NCT02950467 (25) [back to overview]Change in Average Score on Subscales of Group Questionnaire Pre-drug vs Post-drug
NCT02950467 (25) [back to overview]Subject Recruitment and Retention
NCT02950467 (25) [back to overview]Change From Baseline in Experiences in Closer Relationships-M16 (Avoidance) at 3-month Follow-up

GRID-HAM-D-17 -- Structured Interview Guide for the Hamilton Depression Scale.

The GRID-Hamilton Depression Rating Scale is a 17-item clinician-administered rating scale designed to assess severity of depressive symptoms. The score range for the GRID-HAMD is 0 to 52, with higher score indicating more severe depression. For this clinician-rated measure, a clinically significant response was defined as ā©¾50% decrease in measure relative to Baseline; symptom remission was defined as ā©¾50% decrease in measure relative to Baseline and a score of ā©½7 on the GRID-HAMD (NCT00465595)
Timeframe: Baseline, 5 weeks post session 1 and 2, 6-month follow-up

Interventionunits on a scale (Mean)
Low-Dose First Baseline22.32
Low-Dose First Post Session 114.8
Low-Dose First Post Session 26.5
Low-Dose First 6 Month6.95
High-Dose First Baseline22.84
High-Dose First Post Session 16.64
High-Dose First Post Session 26.52
High-Dose First 6 Month6.23

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HAM-A Assessed With the SIGH-A -- a Structured Interview Guide for the Hamilton Anxiety Rating Scale (SIGH-A).

"The Hamilton Anxiety Rating Scale is a 14-item clinician-administered rating scale designed to assess severity of anxiety symptoms. The score range for the HAM-A is 0 to 56, with higher score indicating more severe anxiety.~For this clinician-rated measure, a clinically significant response was defined as ā©¾50% decrease in measure relative to Baseline; symptom remission was defined as ā©¾50% decrease in measure relative to Baseline and a score of ā©½7 on the GRID-HAM-A" (NCT00465595)
Timeframe: Baseline, 5 weeks post session 1 and 2, 6-month follow-up

Interventionunits on a scale (Mean)
Low-Dose First Baseline25.68
Low-Dose First Post Session 116.64
Low-Dose First Post Session 28.92
Low-Dose First 6 Month7.95
High-Dose First Baseline25.73
High-Dose First Post Session 18.48
High-Dose First Post Session 27.52
High-Dose First 6 Month7.04

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QoL Physical Health Scale

4-20 (higher score improved quality of life domain) (NCT00957359)
Timeframe: 2 weeks post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin16.0
Niacin First, Then Psilocybin12.44

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QoL Physical Health Scale

4-20 (higher score improved quality of life domain) (NCT00957359)
Timeframe: 2-4 weeks prior to drug administration/ Baseline

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin15.14
Niacin First, Then Psilocybin12.53

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QoL Physical Health Scale

4-20 (higher score improved quality of life domain) (NCT00957359)
Timeframe: 26 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin16.77
Niacin First, Then Psilocybin14.14

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QoL Psychological Scale

4-20 (higher score improved quality of life domain) (NCT00957359)
Timeframe: 2 weeks post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin15.43
Niacin First, Then Psilocybin12.28

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QoL Psychological Scale

4-20 (higher score improved quality of life domain) (NCT00957359)
Timeframe: 2-4 weeks prior to drug administration/ Baseline

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin13.57
Niacin First, Then Psilocybin12.67

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QoL Psychological Scale

4-20 (higher score improved quality of life domain) (NCT00957359)
Timeframe: 26 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin15.78
Niacin First, Then Psilocybin14.90

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QoL Social Relationships Scale

4-20 (higher score improved quality of life domain) (NCT00957359)
Timeframe: 2 weeks post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin14.86
Niacin First, Then Psilocybin12.78

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QoL Social Relationships Scale

4-20 (higher score improved quality of life domain) (NCT00957359)
Timeframe: 2-4 weeks prior to drug administration/ Baseline

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin13.62
Niacin First, Then Psilocybin13.24

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HADS Anxiety

Hospital Anxiety and Depression Scale (HADS) used for measuring anxiety; Scored on a scale of 0-21 (higher score more anxiety) (NCT00957359)
Timeframe: 26 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin2.69
Niacin First, Then Psilocybin4.70

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QoL Social Relationships Scale

4-20 (higher score improved quality of life domain) (NCT00957359)
Timeframe: 26 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin15.6
Niacin First, Then Psilocybin13.71

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STAI State

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 1 day post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin27.5
Niacin First, Then Psilocybin40.33

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STAI State

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 1 day post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin25.73
Niacin First, Then Psilocybin38.11

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STAI State

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 1 day prior to drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin39.07
Niacin First, Then Psilocybin45.6

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STAI State

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 1 day prior to drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin32.72
Niacin First, Then Psilocybin45.31

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STAI State

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 26 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin28.04
Niacin First, Then Psilocybin38.28

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STAI State

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 6 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin30.67
Niacin First, Then Psilocybin37.77

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STAI Trait

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 1 day post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin27.5
Niacin First, Then Psilocybin44

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STAI Trait

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 1 day post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin25.73
Niacin First, Then Psilocybin38.11

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STAI Trait

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 1 day prior to drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin39.07
Niacin First, Then Psilocybin45.87

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STAI Trait

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 1 day prior to drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin32.72
Niacin First, Then Psilocybin45.31

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STAI Trait

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 2-4 weeks prior to drug administration/ Baseline

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin43.79
Niacin First, Then Psilocybin48.53

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STAI Trait

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 6 weeks post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin33.5
Niacin First, Then Psilocybin46.19

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STAI Trait

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 6 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin28.04
Niacin First, Then Psilocybin38.28

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STAI Trait

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 6 weeks prior to drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin30.67
Niacin First, Then Psilocybin37.77

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State-Trait Anxiety Inventory (STAI) State

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 2-4 weeks prior to drug administration/ Baseline

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin43.79
Niacin First, Then Psilocybin48.53

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Death Anxiety Scale

0-15 (higher score more death anxiety) (NCT00957359)
Timeframe: 2 weeks post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin6.57
Niacin First, Then Psilocybin7.85

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Death Anxiety Scale

0-15 (higher score more death anxiety) (NCT00957359)
Timeframe: 2-4 weeks prior to drug administration/ Baseline

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin9.14
Niacin First, Then Psilocybin8.13

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Death Anxiety Scale

0-15 (higher score more death anxiety) (NCT00957359)
Timeframe: 26 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin6.71
Niacin First, Then Psilocybin6.83

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Death Transcendence Scale

0-60 (higher score more death transcendence) (NCT00957359)
Timeframe: 2 weeks post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin33.98
Niacin First, Then Psilocybin19.88

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Death Transcendence Scale

0-60 (higher score more death transcendence) (NCT00957359)
Timeframe: 2-4 weeks prior to drug administration/ Baseline

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin13.64
Niacin First, Then Psilocybin11.27

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Demoralization Scale

0-96 (higher score more demoralized) (NCT00957359)
Timeframe: 2 weeks post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin18.79
Niacin First, Then Psilocybin32.79

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Demoralization Scale

0-96 (higher score more demoralized) (NCT00957359)
Timeframe: 2-4 weeks prior to drug administration/ Baseline

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin35.71
Niacin First, Then Psilocybin38.07

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Demoralization Scale

0-96 (higher score more demoralized) (NCT00957359)
Timeframe: 26 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin19.38
Niacin First, Then Psilocybin24.58

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HADS Anxiety

0-21 (higher score more anxiety) (NCT00957359)
Timeframe: 1 day post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin6.84
Niacin First, Then Psilocybin13.02

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HADS Anxiety

Hospital Anxiety and Depression Scale (HADS) used for measuring anxiety; Scored on a scale of 0-21 (higher score more anxiety) (NCT00957359)
Timeframe: 1 day post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin3.43
Niacin First, Then Psilocybin6.0

[back to top]

HADS Anxiety

Hospital Anxiety and Depression Scale (HADS) used for measuring anxiety; Scored on a scale of 0-21 (higher score more anxiety) (NCT00957359)
Timeframe: 1 day prior to drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin9.0
Niacin First, Then Psilocybin9.0

[back to top]

HADS Anxiety

Hospital Anxiety and Depression Scale (HADS) used for measuring anxiety; Scored on a scale of 0-21 (higher score more anxiety) (NCT00957359)
Timeframe: 1 day prior to drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin4.57
Niacin First, Then Psilocybin7.98

[back to top]

HADS Anxiety

Hospital Anxiety and Depression Scale (HADS) used for measuring anxiety; Scored on a scale of 0-21 (higher score more anxiety) (NCT00957359)
Timeframe: 2-4 weeks prior to drug administration

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin15.14
Niacin First, Then Psilocybin16.93

[back to top]

STAI State

"STAI scores 20-80 (higher score more anxiety). Commonly classified as no or low anxiety (20-37), moderate anxiety (38-44), and high anxiety (45-80)." (NCT00957359)
Timeframe: 6 weeks post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin33.5
Niacin First, Then Psilocybin47.05

[back to top]

HADS Anxiety

Hospital Anxiety and Depression Scale (HADS) used for measuring anxiety; Scored on a scale of 0-21 (higher score more anxiety) (NCT00957359)
Timeframe: 6 weeks post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin4.64
Niacin First, Then Psilocybin8.44

[back to top]

HADS Anxiety

Hospital Anxiety and Depression Scale (HADS) used for measuring anxiety; Scored on a scale of 0-21 (higher score more anxiety) (NCT00957359)
Timeframe: 6 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin3.60
Niacin First, Then Psilocybin5.54

[back to top]

HADS Depression

0-21 (higher score more depression) (NCT00957359)
Timeframe: 1 day prior to drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin10.43
Niacin First, Then Psilocybin16.47

[back to top]

HADS Depression

0-21 (higher score more depression) (NCT00957359)
Timeframe: 2-4 weeks prior to drug administration/ Baseline

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin5.29
Niacin First, Then Psilocybin7

[back to top]

HADS Depression

Hospital Anxiety and Depression Scale (HADS) used for measuring depression; Scored on a scale of 0-21 (higher score more depression) (NCT00957359)
Timeframe: 1 day post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin4.21
Niacin First, Then Psilocybin12.07

[back to top]

HADS Depression

Hospital Anxiety and Depression Scale (HADS) used for measuring depression; Scored on a scale of 0-21 (higher score more depression) (NCT00957359)
Timeframe: 1 day post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin5.25
Niacin First, Then Psilocybin10.05

[back to top]

HADS Depression

Hospital Anxiety and Depression Scale (HADS) used for measuring depression; Scored on a scale of 0-21 (higher score more depression) (NCT00957359)
Timeframe: 26 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin6.48
Niacin First, Then Psilocybin9.06

[back to top]

HADS Depression

Hospital Anxiety and Depression Scale (HADS) used for measuring depression; Scored on a scale of 0-21 (higher score more depression) (NCT00957359)
Timeframe: 6 weeks post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin6.5
Niacin First, Then Psilocybin14.24

[back to top]

HADS Depression

Hospital Anxiety and Depression Scale (HADS) used for measuring depression; Scored on a scale of 0-21 (higher score more depression) (NCT00957359)
Timeframe: 6 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin6.31
Niacin First, Then Psilocybin9.65

[back to top]

Hopelessness

0-16 (higher score more hopeless) (NCT00957359)
Timeframe: 2 weeks post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin2.79
Niacin First, Then Psilocybin6.08

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Hopelessness

0-16 (higher score more hopeless) (NCT00957359)
Timeframe: 26 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin2.30
Niacin First, Then Psilocybin3.86

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Hopelessness

0-16 (higher score more hopeless) (NCT00957359)
Timeframe: Baseline

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin5.71
Niacin First, Then Psilocybin6.73

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QoL Environment Scale

4-20 (higher score improved quality of life domain) (NCT00957359)
Timeframe: 2 weeks post drug administration 1

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin16.42
Niacin First, Then Psilocybin13.90

[back to top]

QoL Environment Scale

4-20 (higher score improved quality of life domain) (NCT00957359)
Timeframe: 2-4 weeks prior to drug administration/ Baseline

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin15.75
Niacin First, Then Psilocybin14.93

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QoL Environment Scale

4-20 (higher score improved quality of life domain) (NCT00957359)
Timeframe: 26 weeks post drug administration 2

Interventionscore on a scale (Mean)
Psilocybin First, Then Niacin16.96
Niacin First, Then Psilocybin15.82

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Change From Baseline in Antiretroviral Medication Adherence Scale at 3-month Follow-up

Self-report last-month antiviral medication adherence. Minimum = 0%. Maximum = 100%. Higher scores mean a better outcome. (NCT02950467)
Timeframe: Baseline and 3-month follow-up

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-0.94

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Change From Baseline in Antiretroviral Medication Adherence Scale at End-of-treatment

Self-report last-month antiviral medication adherence. Minimum = 0%. Maximum = 100%. Higher scores mean a better outcome. (NCT02950467)
Timeframe: Baseline and end-of-treatment (7 weeks duration)

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-0.71

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Change From Baseline in Center for Epidemiologic Studies Depression Scale-Revised at 3-month Follow-up

Depression self-report measure. Minimum = 0. Maximum = 60. Higher scores mean a worse outcome. (NCT02950467)
Timeframe: Baseline and 3-month follow-up

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-8.89

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Change From Baseline in Center for Epidemiologic Studies Depression Scale-Revised at End-of-treatment

Depression self-report measure. Minimum = 0. Maximum = 60. Higher scores mean a worse outcome. (NCT02950467)
Timeframe: Baseline and end-of-treatment (7 weeks duration)

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-8.94

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Change From Baseline in Demoralization Scale-II at 3-month Follow-up

Demoralization self-report measure. Minimum = 0. Maximum = 32. Higher scores mean a worse outcome. (NCT02950467)
Timeframe: Baseline and 3-month follow-up

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-5.78

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Change From Baseline in Demoralization Scale-II at End-of-treatment

Demoralization self-report measure. Minimum = 0. Maximum = 32. Higher scores means a worse outcome. (NCT02950467)
Timeframe: Baseline and end-of-treatment (7 weeks duration)

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-6.67

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Change From Baseline in Experiences in Closer Relationships-M16 (Anxiety) at 3-month Follow-up

Self-report measure of attachment anxiety. Minimum = 8. Maximum = 56. Higher scores mean worse outcomes. (NCT02950467)
Timeframe: Baseline and 3-month follow-up

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-3.33

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Change From Baseline in Experiences in Closer Relationships-M16 (Anxiety) at End-of-treatment

Self-report measure of attachment anxiety. Minimum = 8. Maximum = 56. Higher scores mean worse outcomes. (NCT02950467)
Timeframe: Baseline and end-of-treatment (7 weeks duration)

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-0.78

[back to top]

Change From Baseline in Experiences in Closer Relationships-M16 (Avoidance) at End-of-treatment

Self-report measure of attachment avoidance. Minimum = 8. Maximum = 56. Higher scores mean worse outcomes. (NCT02950467)
Timeframe: Baseline and end-of-treatment (7 weeks duration)

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-2.72

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Change From Baseline in Inventory of Complicated Grief at 3-month Follow-up

Complicated Grief self-report measure. Minimum = 0, Maximum = 76. Higher scores mean worse outcome. (NCT02950467)
Timeframe: Baseline and 3-month follow-up

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-7.06

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Change From Baseline in Inventory of Complicated Grief-Revised at End-of-treatment

Complicated Grief self-report measure. Minimum = 0, Maximum = 76. Higher scores mean worse outcome. (NCT02950467)
Timeframe: Baseline and end-of-treatment (7 weeks duration)

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-6.22

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Change From Baseline in McGill Quality of Life Questionnaire-Revised (Overall) at 3-month Follow-up

Self-report quality of life measure. Only item A) Overall quality of life. Minimum = 0 (Very bad). Maximum = 10 (Excellent). Higher scores mean better outcomes. (NCT02950467)
Timeframe: Baseline and 3-month follow-up

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin0.94

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Change From Baseline in McGill Quality of Life Questionnaired-Revised (Overall) at End-of-treatment

Self-report quality of life measure. Only item A) Overall quality of life. Minimum = 0 (Very bad). Maximum = 10 (Excellent). Higher scores mean better outcomes. (NCT02950467)
Timeframe: Baseline and end-of-treatment (7 weeks duration)

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin2.0

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Change From Baseline in PTSD Checklist 5 at 3-month Follow-up

PTSD self-report measure. Minimum = 0. Maximum = 80. Higher scores mean a worse outcome. (NCT02950467)
Timeframe: Baseline and 3-month follow-up

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-7.11

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Change From Baseline in PTSD Checklist 5 at End-of-treatment

PTSD self-report measure. Minimum = 0. Maximum = 80. Higher scores mean a worse outcome. (NCT02950467)
Timeframe: Baseline and end-of-treatment (7 weeks duration)

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-9

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Change From Baseline in State-Trait Anxiety Inventory (State) at 3-month Follow-up

State anxiety self-report measure. Minimum = 0. Maximum = 80. Higher scores mean a worse outcome. (NCT02950467)
Timeframe: Baseline and 3-month follow-up

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin1.06

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Change From Baseline in State-Trait Anxiety Inventory (State) at End-of-treatment

State anxiety self-report measure. Minimum = 0. Maximum = 80. Higher scores mean a worse outcome. (NCT02950467)
Timeframe: Baseline and end-of-treatment (7 weeks duration)

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-5.56

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Change From Baseline in State-Trait Anxiety Inventory (Trait) at 3-month Follow-up

Trait anxiety self-report measure. Minimum = 0. Maximum = 80. Higher scores mean a worse outcome. (NCT02950467)
Timeframe: Baseline and 3-month follow-up

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-3.39

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Change From Baseline in State-Trait Anxiety Inventory (Trait) at End-of-treatment

Trait anxiety self-report measure. Minimum = 0. Maximum = 80. Higher scores mean a worse outcome. (NCT02950467)
Timeframe: Baseline and end-of-treatment (7 weeks duration)

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-6.06

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Change in Average Score on Subscales of Group Questionnaire Pre-drug vs Post-drug

The Group Questionnaire is a self-report measure with three sub-scales that measure Positive Bonding, Positive Working and Negative Relationship dimensions of the relationships at 3 levels: between group members, between group members and group therapists, and between group members and the group as a whole. Each subscale score is calculated by summation of the ratings across all three levels for each subscale. Positive Bonding scores range from 13 to 91 with higher scores indicating a better outcome. Positive Working scores range 8 to 56 with higher scores indicating a better outcome. Negative Relationship scores range 9 to 63 with higher scores indicating worse outcomes. (NCT02950467)
Timeframe: Mean scores averaged over 2 weeks pre-medication compared to 3 weeks post-medication.

Interventionscore on a scale (Mean)
Positive Bonding (Overall)Positive Working (Overall)Negative Relationship (Overall)
Group Therapy Plus Psilocybin2.611.87-0.69

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Subject Recruitment and Retention

Two therapy groups of at least 4 subjects each will complete the study (NCT02950467)
Timeframe: Duration of study, about 24 months

InterventionParticipants (Count of Participants)
EnrolledCompleted Safety Assessment at End-of-treatmentCompleted Safety Assessment at 3-month follow-up
Group Therapy Plus Psilocybin181818

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Change From Baseline in Experiences in Closer Relationships-M16 (Avoidance) at 3-month Follow-up

Self-report measure of attachment avoidance. Minimum = 8. Maximum = 56. Higher scores mean worse outcomes. (NCT02950467)
Timeframe: Baseline and 3-month follow-up

Interventionunits on a scale (Mean)
Group Therapy Plus Psilocybin-0.06

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