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Details

Stereochemistry ACHIRAL
Molecular Formula C12H16N2
Molecular Weight 188.2693
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMETHYLTRYPTAMINE

SMILES

CN(C)CCc1c[nH]c2ccccc12

InChI

InChIKey=DMULVCHRPCFFGV-UHFFFAOYSA-N
InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C12H16N2
Molecular Weight 188.2693
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
A proposed mechanism for the visions of dream sleep.
1988 Jun
Dose-response study of N,N-dimethyltryptamine in humans. I. Neuroendocrine, autonomic, and cardiovascular effects.
1994 Feb
[Antimycobacterial indole derivatives].
1994 Feb
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-hydroxytryptamine and [3H]alniditan.
1996 Dec
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.
1996 Jan
Psychedelic effects of ketamine in healthy volunteers: relationship to steady-state plasma concentrations.
1998 Jan
Various alkaloid profiles in decoctions of Banisteriopsis caapi.
2005 Jun
A fatal intoxication following the ingestion of 5-methoxy-N,N-dimethyltryptamine in an ayahuasca preparation.
2005 Nov-Dec
Urinary excretion of dietary contaminants in horses.
2006 Aug
The mysterious trace amines: protean neuromodulators of synaptic transmission in mammalian brain.
2006 Aug
The adverse effects of hallucinogens from intramural perspective.
2006 Dec
Detection and determination of abused hallucinogens in biological material.
2006 Dec
Increased frontal and paralimbic activation following ayahuasca, the pan-Amazonian inebriant.
2006 May
Not imagining it. Research into hallucinogens cautiously resumes.
2006 Nov
NMR spectral assignments of a new chlorotryptamine alkaloid and its analogues from Acacia confusa.
2007 Apr
DMT at fifty.
2007 Dec
Risk assessment of ritual use of oral dimethyltryptamine (DMT) and harmala alkaloids.
2007 Jan
Effects of ayahuasca on psychometric measures of anxiety, panic-like and hopelessness in Santo Daime members.
2007 Jul 25
Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors.
2007 Mar 15
Secondary metabolites from three Florida sponges with antidepressant activity.
2008 Feb
Daytime Ayahuasca administration modulates REM and slow-wave sleep in healthy volunteers.
2008 Feb
A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation.
2008 Jan 15
Mismatch negativity generation in the human 5HT2A agonist and NMDA antagonist model of psychosis.
2008 Jul
Halogenated solvent interactions with N,N-dimethyltryptamine: formation of quaternary ammonium salts and their artificially induced rearrangements during analysis.
2008 Jul 4
The "vine of the soul" vs. the Controlled Substances Act: implications of the hoasca case.
2008 Jun
[Inhibition of return in schizophrenia: a review].
2008 Jun
[Hallucinogen-induced psychological disorders].
2008 Jun
Indolealkylamines: biotransformations and potential drug-drug interactions.
2008 Jun
Ayahuasca versus violence--a case report.
2008 May
N,N-Dimethyltryptamine and dichloromethane: rearrangement of quaternary ammonium salt product during GC-EI and CI-MS-MS analysis.
2008 May 12
Pharmacological modulation of the neural basis underlying inhibition of return (IOR) in the human 5-HT2A agonist and NMDA antagonist model of psychosis.
2008 Nov
Modification of the effects of 5-methoxy-N,N-dimethyltryptamine on exploratory behavior in rats by monoamine oxidase inhibitors.
2008 Nov
Identification of N,N-dimethyltryptamine and beta-carbolines in psychotropic ayahuasca beverage.
2008 Oct
[Studies on constituents of rootsanel leaves from Desmodium blandum and their cytotoxic activity against growth of several tumor cells].
2008 Sep
Serotonin 5-HT(2A) Receptor Function as a Contributing Factor to Both Neuropsychiatric and Cardiovascular Diseases.
2009
A multi-component LC-MS/MS method for detection of ten plant-derived psychoactive substances in urine.
2009 Apr 15
Characterisation of a proposed internet synthesis of N,N-dimethyltryptamine using liquid chromatography/electrospray ionisation tandem mass spectrometry.
2009 Aug 14
Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter.
2009 Dec
The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator.
2009 Feb 13
Comparison of the discriminative stimulus effects of dimethyltryptamine with different classes of psychoactive compounds in rats.
2009 Jul
[Simple and rapid screening for psychotropic natural products using Direct Analysis in Real Time (DART)-TOFMS].
2009 Jun
Analysis of toxic alkaloids in body samples.
2009 Mar 10
The neural correlates of religious and nonreligious belief.
2009 Oct 1
Sigma receptors in oncology: therapeutic and diagnostic applications of sigma ligands.
2010
The chemical basis of pharmacology.
2010 Dec 7
Antioxidant effects of ethyl acetate extract of Desmodium gangeticum root on myocardial ischemia reperfusion injury in rat hearts.
2010 Jan 22
Tinnitus psychopharmacology: A comprehensive review of its pathomechanisms and management.
2010 Jun 24
Association between Serotonin-Related Polymorphisms in 5HT2A, TPH1, TPH2 Genes and Bipolar Disorder in Korean Population.
2010 Mar
Dimethyltryptamine (DMT): subjective effects and patterns of use among Australian recreational users.
2010 Sep 1
The hallucinogenic world of tryptamines: an updated review.
2015 Aug
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Jun 25 21:30:21 UTC 2021
Edited
by admin
on Fri Jun 25 21:30:21 UTC 2021
Record UNII
WUB601BHAA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIMETHYLTRYPTAMINE
MART.   WHO-DD  
Systematic Name English
DIMETHYLTRYPTAMINE [MART.]
Common Name English
N-DIMETHYLTRYPTAMINE
Common Name English
DMT
Common Name English
2-(3-INDOLYL)ETHYLDIMETHYLAMINE
Systematic Name English
N,N-DIMETHYLTRYPTAMINE
MI  
Systematic Name English
NSC-63795
Code English
3-(2-(DIMETHYLAMINO)ETHYL)INDOLE
Systematic Name English
3-(2-DIMETHYLAMINOETHYL)INDOLE
Systematic Name English
DEA NO. 7435
Code English
DIMETHYLTRYPTAMINE [WHO-DD]
Common Name English
N,N-DIMETHYL-1H-INDOLE-3-ETHANAMINE
Systematic Name English
N,N-DIMETHYLTRYPTAMINE [MI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 813521
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
DEA NO. 7435
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
Code System Code Type Description
WIKIPEDIA
DIMETHYLTRYPTAMINE
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-508-4
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
PRIMARY
EPA CompTox
61-50-7
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
PRIMARY
CAS
61-50-7
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
PRIMARY
PUBCHEM
6089
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
PRIMARY
FDA UNII
WUB601BHAA
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
PRIMARY
MERCK INDEX
M4558
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
PRIMARY Merck Index
HSDB
8017
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
PRIMARY
INCB IDS CODE
PD 004
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
PRIMARY
DRUG BANK
DB01488
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
PRIMARY
EVMPD
SUB33250
Created by admin on Fri Jun 25 21:30:21 UTC 2021 , Edited by admin on Fri Jun 25 21:30:21 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
TARGET -> AGONIST
AGONIST
Ki
PARENT -> CONSTITUENT ALWAYS PRESENT
TARGET -> AGONIST
all of the tryptamines, including DMT but with the exception of psilocin, were more potent agonists at the 5-HT2A receptor than LSD in the assay that was used in the present study. LSD and psilocin were 5-HT2A receptor partial agonists, with 28% and 16% activation efficacy, respectively, whereas all of the other compounds presented higher 5-HT2A receptor activation efficacies (up to >80% for DiPT and 5-MeO-MiPT).
EC50
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY