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Details

Stereochemistry ACHIRAL
Molecular Formula C12H16N2.C4H4O4
Molecular Weight 304.341
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DIMETHYLTRYPTAMINE FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.CN(C)CCC1=CNC2=CC=CC=C12

InChI

InChIKey=OHMVTPSXVQQKPA-WLHGVMLRSA-N
InChI=1S/C12H16N2.C4H4O4/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12;5-3(6)1-2-4(7)8/h3-6,9,13H,7-8H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
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
Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L.
2004
Potentially hallucinogenic 5-hydroxytryptamine receptor ligands bufotenine and dimethyltryptamine in blood and tissues.
2005
Endogenous psychoactive tryptamines reconsidered: an anxiolytic role for dimethyltryptamine.
2005
Fast and slow metabolizers of Hoasca.
2005 Jun
Psychological effects of (S)-ketamine and N,N-dimethyltryptamine (DMT): a double-blind, cross-over study in healthy volunteers.
2005 Nov
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
Detection and determination of abused hallucinogens in biological material.
2006 Dec
Pharmacologic analysis of non-synonymous coding h5-HT2A SNPs reveals alterations in atypical antipsychotic and agonist efficacies.
2006 Jan-Feb
Increased frontal and paralimbic activation following ayahuasca, the pan-Amazonian inebriant.
2006 May
Not imagining it. Research into hallucinogens cautiously resumes.
2006 Nov
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
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
The globalization of ayahuasca: harm reduction or benefit maximization?
2008 Aug
Secondary metabolites from three Florida sponges with antidepressant activity.
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
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
Reassessing the cultural and psychopharmacological significance of Banisteriopsis caapi: preparation, classification and use among the Piaroa of Southern Venezuela.
2008 Sep
A multi-component LC-MS/MS method for detection of ten plant-derived psychoactive substances in urine.
2009 Apr 15
Optimization of separation and online sample concentration of N,N-dimethyltryptamine and related compounds using MEKC.
2009 Feb
Analysis of toxic alkaloids in body samples.
2009 Mar 10
Gas chromatographic analysis of dimethyltryptamine and beta-carboline alkaloids in ayahuasca, an Amazonian psychoactive plant beverage.
2009 Mar-Apr
The neural correlates of religious and nonreligious belief.
2009 Oct 1
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
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
Patents

Patents

Substance Class Chemical
Created
by admin
on Sun Dec 18 00:14:36 UTC 2022
Edited
by admin
on Sun Dec 18 00:14:36 UTC 2022
Record UNII
EP5189LWFM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIMETHYLTRYPTAMINE FUMARATE
Systematic Name English
1H-INDOLE-3-ETHANAMINE, N,N-DIMETHYL-, (2E)-2-BUTENEDIOATE (1:1)
Systematic Name English
N,N-DIMETHYLTRYPTAMINE FUMARATE
Systematic Name English
1H-INDOLE-3-ETHANAMINE, N,N-DIMETHYL-, (E)-2-BUTENEDIOATE (1:1)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID0048896
Created by admin on Sun Dec 18 00:14:36 UTC 2022 , Edited by admin on Sun Dec 18 00:14:36 UTC 2022
PRIMARY
FDA UNII
EP5189LWFM
Created by admin on Sun Dec 18 00:14:36 UTC 2022 , Edited by admin on Sun Dec 18 00:14:36 UTC 2022
PRIMARY
CAS
68677-26-9
Created by admin on Sun Dec 18 00:14:36 UTC 2022 , Edited by admin on Sun Dec 18 00:14:36 UTC 2022
PRIMARY
PUBCHEM
60196335
Created by admin on Sun Dec 18 00:14:36 UTC 2022 , Edited by admin on Sun Dec 18 00:14:36 UTC 2022
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY