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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

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
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
The globalization of ayahuasca: harm reduction or benefit maximization?
2008 Aug
Secondary metabolites from three Florida sponges with antidepressant activity.
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
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
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
[Simple and rapid screening for psychotropic natural products using Direct Analysis in Real Time (DART)-TOFMS].
2009 Jun
When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor.
2009 Mar 10
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
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

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 Sat Dec 16 08:46:51 GMT 2023 , Edited by admin on Sat Dec 16 08:46:51 GMT 2023
PRIMARY
FDA UNII
EP5189LWFM
Created by admin on Sat Dec 16 08:46:51 GMT 2023 , Edited by admin on Sat Dec 16 08:46:51 GMT 2023
PRIMARY
CAS
68677-26-9
Created by admin on Sat Dec 16 08:46:51 GMT 2023 , Edited by admin on Sat Dec 16 08:46:51 GMT 2023
PRIMARY
PUBCHEM
60196335
Created by admin on Sat Dec 16 08:46:51 GMT 2023 , Edited by admin on Sat Dec 16 08:46:51 GMT 2023
PRIMARY
SMS_ID
300000047760
Created by admin on Sat Dec 16 08:46:51 GMT 2023 , Edited by admin on Sat Dec 16 08:46:51 GMT 2023
PRIMARY