U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H16N2.ClH
Molecular Weight 224.73
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMETHYLTRYPTAMINE HYDROCHLORIDE

SMILES

Cl.CN(C)CCC1=CNC2=CC=CC=C12

InChI

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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C12H16N2
Molecular Weight 188.2688
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
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
A quantitative synthesis of the medicinal ethnobotany of the Malinké of Mali and the Asháninka of Peru, with a new theoretical framework.
2007 Dec 5
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
Prepulse inhibition of the startle reflex and its attentional modulation in the human S-ketamine and N,N-dimethyltryptamine (DMT) models of psychosis.
2007 May
Daytime Ayahuasca administration modulates REM and slow-wave sleep in healthy volunteers.
2008 Feb
Comparison of the separation of nine tryptamine standards based on gas chromatography, high performance liquid chromatography and capillary electrophoresis methods.
2008 Feb 15
A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation.
2008 Jan 15
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
N,N-Dimethyltryptamine and dichloromethane: rearrangement of quaternary ammonium salt product during GC-EI and CI-MS-MS analysis.
2008 May 12
Modification of the effects of 5-methoxy-N,N-dimethyltryptamine on exploratory behavior in rats by monoamine oxidase inhibitors.
2008 Nov
Reassessing the cultural and psychopharmacological significance of Banisteriopsis caapi: preparation, classification and use among the Piaroa of Southern Venezuela.
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
Optimization of separation and online sample concentration of N,N-dimethyltryptamine and related compounds using MEKC.
2009 Feb
The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator.
2009 Feb 13
Bioanalytical and clinical evaluation of 103 suspected cases of intoxications with psychoactive plant materials.
2009 Jul
Comparison of the discriminative stimulus effects of dimethyltryptamine with different classes of psychoactive compounds in rats.
2009 Jul
When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor.
2009 Mar 10
Gas chromatographic analysis of dimethyltryptamine and beta-carboline alkaloids in ayahuasca, an Amazonian psychoactive plant beverage.
2009 Mar-Apr
Predicting new molecular targets for known drugs.
2009 Nov 12
The neural correlates of religious and nonreligious belief.
2009 Oct 1
Sigma receptors in oncology: therapeutic and diagnostic applications of sigma ligands.
2010
Psychometric evaluation of the altered states of consciousness rating scale (OAV).
2010 Aug 31
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
Characterization of the synthesis of N,N-dimethyltryptamine by reductive amination using gas chromatography ion trap mass spectrometry.
2010 Jul
Alkaloids from Fissistigma latifolium (Dunal) Merr.
2010 Jun 24
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
Neuronal correlates of visual and auditory alertness in the DMT and ketamine model of psychosis.
2010 Oct
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 Dec 16 16:52:50 UTC 2022
Edited
by admin
on Fri Dec 16 16:52:50 UTC 2022
Record UNII
PRC2H3HFU4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIMETHYLTRYPTAMINE HYDROCHLORIDE
Systematic Name English
DMT HYDROCHLORIDE [INCB GREEN LIST]
Common Name English
1H-INDOLE-3-ETHANAMINE, N,N-DIMETHYL-, HYDROCHLORIDE (1:1)
Systematic Name English
1H-INDOLE-3-ETHANAMINE, N,N-DIMETHYL-, MONOHYDROCHLORIDE
Systematic Name English
N,N-DIMETHYLTRYPTAMINE HYDROCHLORIDE
Systematic Name English
INDOLE, 3-(2-(DIMETHYLAMINO)ETHYL)-, MONOHYDROCHLORIDE
Systematic Name English
Code System Code Type Description
FDA UNII
PRC2H3HFU4
Created by admin on Fri Dec 16 16:52:50 UTC 2022 , Edited by admin on Fri Dec 16 16:52:50 UTC 2022
PRIMARY
CAS
2826-93-9
Created by admin on Fri Dec 16 16:52:50 UTC 2022 , Edited by admin on Fri Dec 16 16:52:50 UTC 2022
PRIMARY
INCB IDS CODE
PD 004
Created by admin on Fri Dec 16 16:52:50 UTC 2022 , Edited by admin on Fri Dec 16 16:52:50 UTC 2022
PRIMARY
PUBCHEM
25944
Created by admin on Fri Dec 16 16:52:50 UTC 2022 , Edited by admin on Fri Dec 16 16:52:50 UTC 2022
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY