Dimethyltryptamine

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H16N2
Molecular Weight	188.2688
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCC1=CNC2=C1C=CC=C2

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	188.2688
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1a (5-HT1a) receptor 177 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1828347	Agonist 2752
Serotonin 2 receptors; 5-HT2a & 5-HT2c 7 Target ID: CHEMBL2096662 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9768567	Agonist 2752
Adrenergic receptor alpha-2 114 Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27216487	Binding Agent 1076
Adrenergic receptor alpha-1 171 Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27216487	Binding Agent 1076
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27216487	Binding Agent 1076

PubMed

Title	Date	PubMed
The hallucinogenic world of tryptamines: an updated review.	2015-08	25877327
The chemical basis of pharmacology.	2010-12-07	21058655
Neuronal correlates of visual and auditory alertness in the DMT and ketamine model of psychosis.	2010-10	19304859
Dimethyltryptamine (DMT): subjective effects and patterns of use among Australian recreational users.	2010-09-01	20570058
Psychometric evaluation of the altered states of consciousness rating scale (OAV).	2010-08-31	20824211
Characterization of the synthesis of N,N-dimethyltryptamine by reductive amination using gas chromatography ion trap mass spectrometry.	2010-07	20648523
Alkaloids from Fissistigma latifolium (Dunal) Merr.	2010-06-24	20657378
Tinnitus psychopharmacology: A comprehensive review of its pathomechanisms and management.	2010-06-24	20628627
Association between Serotonin-Related Polymorphisms in 5HT2A, TPH1, TPH2 Genes and Bipolar Disorder in Korean Population.	2010-03	20396435
Antioxidant effects of ethyl acetate extract of Desmodium gangeticum root on myocardial ischemia reperfusion injury in rat hearts.	2010-01-22	20180993
Sigma receptors in oncology: therapeutic and diagnostic applications of sigma ligands.	2010	21050178
Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter.	2009-12	19756361
Predicting new molecular targets for known drugs.	2009-11-12	19881490
The neural correlates of religious and nonreligious belief.	2009-10-01	19794914
Characterisation of a proposed internet synthesis of N,N-dimethyltryptamine using liquid chromatography/electrospray ionisation tandem mass spectrometry.	2009-08-14	19592003
Bioanalytical and clinical evaluation of 103 suspected cases of intoxications with psychoactive plant materials.	2009-07	19586355
Comparison of the discriminative stimulus effects of dimethyltryptamine with different classes of psychoactive compounds in rats.	2009-07	19288085
[Simple and rapid screening for psychotropic natural products using Direct Analysis in Real Time (DART)-TOFMS].	2009-06	19483414
A multi-component LC-MS/MS method for detection of ten plant-derived psychoactive substances in urine.	2009-04-15	19332394
When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor.	2009-03-10	19278957
Analysis of toxic alkaloids in body samples.	2009-03-10	19147309
The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator.	2009-02-13	19213917
Optimization of separation and online sample concentration of N,N-dimethyltryptamine and related compounds using MEKC.	2009-02	19137528
Gas chromatographic analysis of dimethyltryptamine and beta-carboline alkaloids in ayahuasca, an Amazonian psychoactive plant beverage.	2009-01-14	19140116
Serotonin 5-HT(2A) Receptor Function as a Contributing Factor to Both Neuropsychiatric and Cardiovascular Diseases.	2009	20029624
Pharmacological modulation of the neural basis underlying inhibition of return (IOR) in the human 5-HT2A agonist and NMDA antagonist model of psychosis.	2008-11	18649072
Modification of the effects of 5-methoxy-N,N-dimethyltryptamine on exploratory behavior in rats by monoamine oxidase inhibitors.	2008-11	18604652
Identification of N,N-dimethyltryptamine and beta-carbolines in psychotropic ayahuasca beverage.	2008-10	18506697
[Studies on constituents of rootsanel leaves from Desmodium blandum and their cytotoxic activity against growth of several tumor cells].	2008-09	19160788
Reassessing the cultural and psychopharmacological significance of Banisteriopsis caapi: preparation, classification and use among the Piaroa of Southern Venezuela.	2008-09	19004422
The globalization of ayahuasca: harm reduction or benefit maximization?	2008-08	18638702
Halogenated solvent interactions with N,N-dimethyltryptamine: formation of quaternary ammonium salts and their artificially induced rearrangements during analysis.	2008-07-04	18455334
Mismatch negativity generation in the human 5HT2A agonist and NMDA antagonist model of psychosis.	2008-07	18488201
The "vine of the soul" vs. the Controlled Substances Act: implications of the hoasca case.	2008-06	18720669
[Inhibition of return in schizophrenia: a review].	2008-06	18558147
[Hallucinogen-induced psychological disorders].	2008-06	18512184
Indolealkylamines: biotransformations and potential drug-drug interactions.	2008-06	18454322
N,N-Dimethyltryptamine and dichloromethane: rearrangement of quaternary ammonium salt product during GC-EI and CI-MS-MS analysis.	2008-05-12	18242916
Ayahuasca versus violence--a case report.	2008-05	18959142
Comparison of the separation of nine tryptamine standards based on gas chromatography, high performance liquid chromatography and capillary electrophoresis methods.	2008-02-15	18177659
Secondary metabolites from three Florida sponges with antidepressant activity.	2008-02	18217716
A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation.	2008-01-15	18371669
A quantitative synthesis of the medicinal ethnobotany of the Malinké of Mali and the Asháninka of Peru, with a new theoretical framework.	2007-12-05	18053260
DMT at fifty.	2007-12	18510265
Psychedelic effects of ketamine in healthy volunteers: relationship to steady-state plasma concentrations.	1998-01	9447860
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.	1996-12	8967979
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.	1996-01	8522988
Dose-response study of N,N-dimethyltryptamine in humans. I. Neuroendocrine, autonomic, and cardiovascular effects.	1994-02	8297216
[Antimycobacterial indole derivatives].	1994-02	8135641
A proposed mechanism for the visions of dream sleep.	1988-06	3412201

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:40:59 GMT 2025` Edited by `admin` on `Mon Mar 31 18:40:59 GMT 2025`
Record UNII	WUB601BHAA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Dimethyltryptamine

Official Name

English

N,N-DIMETHYLTRYPTAMINE

Preferred Name

English

DIMETHYLTRYPTAMINE [MART.]

Common Name

English

N-DIMETHYLTRYPTAMINE

Common Name

English

DMT

Common Name

English

2-(3-INDOLYL)ETHYLDIMETHYLAMINE

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

dimethyltryptamine [INN]

Common Name

English

N,N-DIMETHYLTRYPTAMINE [MI]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

813521