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=CC=CC=C12

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1828347	Agonist 2678
Serotonin 2 receptors; 5-HT2a & 5-HT2c 7 Target ID: CHEMBL2096662 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9768567	Agonist 2678
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27216487	Binding Agent 1064
Adrenergic receptor alpha-1 169 Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27216487	Binding Agent 1064
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27216487	Binding Agent 1064

PubMed

Title	Date	PubMed
A versatile linkage strategy for solid-phase synthesis of N,N-dimethyltryptamines and beta-carbolines.	2002 Nov 14	12423079
Determination of N,N-dimethyltryptamine and beta-carboline alkaloids in human plasma following oral administration of Ayahuasca.	2002 Nov 5	12361741
Application of transcerebral, weak (1 microT) complex magnetic fields and mystical experiences: are they generated by field-induced dimethyltryptamine release from the pineal organ?	2003 Dec	15002845
Human pharmacology of ayahuasca: subjective and cardiovascular effects, monoamine metabolite excretion, and pharmacokinetics.	2003 Jul	12660312
Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L.	2004	15270248
Effects of the South American psychoactive beverage ayahuasca on regional brain electrical activity in humans: a functional neuroimaging study using low-resolution electromagnetic tomography.	2004	15179026
Transient reinforcing effects of phenylisopropylamine and indolealkylamine hallucinogens in rhesus monkeys.	2004 Mar	15096915
Hallucinogens and dissociative agents naturally growing in the United States.	2004 May	15163594
Clinical investigations of the therapeutic potential of ayahuasca: rationale and regulatory challenges.	2004 May	15163593
A general screening and confirmation approach to the analysis of designer tryptamines and phenethylamines in blood and urine using GC-EI-MS and HPLC-electrospray-MS.	2004 Sep	15516287
Potentially hallucinogenic 5-hydroxytryptamine receptor ligands bufotenine and dimethyltryptamine in blood and tissues.	2005	16095048
Endogenous psychoactive tryptamines reconsidered: an anxiolytic role for dimethyltryptamine.	2005	15780487
Variation in the accumulation levels of N,N-dimethyltryptamine in micropropagated trees and in in vitro cultures of Mimosa tenuiflora.	2005 Jan	15700647
Fast and slow metabolizers of Hoasca.	2005 Jun	16149329
Can psychedelics have a role in psychiatry once again?	2005 Jun	15928353
Psychological effects of (S)-ketamine and N,N-dimethyltryptamine (DMT): a double-blind, cross-over study in healthy volunteers.	2005 Nov	16342002
The mysterious trace amines: protean neuromodulators of synaptic transmission in mammalian brain.	2006 Aug	16962229
Inhibition of return in the human 5HT2A agonist and NMDA antagonist model of psychosis.	2006 Feb	16123739
NMR spectral assignments of a new chlorotryptamine alkaloid and its analogues from Acacia confusa.	2007 Apr	17310474
DMT at fifty.	2007 Dec	18510265
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	18053260
The globalization of ayahuasca: harm reduction or benefit maximization?	2008 Aug	18638702
Secondary metabolites from three Florida sponges with antidepressant activity.	2008 Feb	18217716
Daytime Ayahuasca administration modulates REM and slow-wave sleep in healthy volunteers.	2008 Feb	18030450
Comparison of the separation of nine tryptamine standards based on gas chromatography, high performance liquid chromatography and capillary electrophoresis methods.	2008 Feb 15	18177659
A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation.	2008 Jan 15	18371669
Mismatch negativity generation in the human 5HT2A agonist and NMDA antagonist model of psychosis.	2008 Jul	18488201
Halogenated solvent interactions with N,N-dimethyltryptamine: formation of quaternary ammonium salts and their artificially induced rearrangements during analysis.	2008 Jul 4	18455334
The "vine of the soul" vs. the Controlled Substances Act: implications of the hoasca case.	2008 Jun	18720669
[Inhibition of return in schizophrenia: a review].	2008 Jun	18558147
[Hallucinogen-induced psychological disorders].	2008 Jun	18512184
Indolealkylamines: biotransformations and potential drug-drug interactions.	2008 Jun	18454322
Ayahuasca versus violence--a case report.	2008 May	18959142
N,N-Dimethyltryptamine and dichloromethane: rearrangement of quaternary ammonium salt product during GC-EI and CI-MS-MS analysis.	2008 May 12	18242916
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	18649072
Modification of the effects of 5-methoxy-N,N-dimethyltryptamine on exploratory behavior in rats by monoamine oxidase inhibitors.	2008 Nov	18604652
Identification of N,N-dimethyltryptamine and beta-carbolines in psychotropic ayahuasca beverage.	2008 Oct	18506697
[Studies on constituents of rootsanel leaves from Desmodium blandum and their cytotoxic activity against growth of several tumor cells].	2008 Sep	19160788
Reassessing the cultural and psychopharmacological significance of Banisteriopsis caapi: preparation, classification and use among the Piaroa of Southern Venezuela.	2008 Sep	19004422
Characterisation of a proposed internet synthesis of N,N-dimethyltryptamine using liquid chromatography/electrospray ionisation tandem mass spectrometry.	2009 Aug 14	19592003
Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter.	2009 Dec	19756361
Optimization of separation and online sample concentration of N,N-dimethyltryptamine and related compounds using MEKC.	2009 Feb	19137528
The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator.	2009 Feb 13	19213917
Bioanalytical and clinical evaluation of 103 suspected cases of intoxications with psychoactive plant materials.	2009 Jul	19586355
When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor.	2009 Mar 10	19278957
Analysis of toxic alkaloids in body samples.	2009 Mar 10	19147309
Gas chromatographic analysis of dimethyltryptamine and beta-carboline alkaloids in ayahuasca, an Amazonian psychoactive plant beverage.	2009 Mar-Apr	19140116
The neural correlates of religious and nonreligious belief.	2009 Oct 1	19794914
Alkaloids from Fissistigma latifolium (Dunal) Merr.	2010 Jun 24	20657378
Tinnitus psychopharmacology: A comprehensive review of its pathomechanisms and management.	2010 Jun 24	20628627

Patents

Name

Type

Language

DIMETHYLTRYPTAMINE

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

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