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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 of DIMETHYLTRYPTAMINE

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
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Agonist
2678
Binding Agent
1064
Binding Agent
1064
Binding Agent
1064
PubMed

PubMed

TitleDatePubMed
A proposed mechanism for the visions of dream sleep.
1988 Jun
[Antimycobacterial indole derivatives].
1994 Feb
5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens.
2002 May
Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L.
2004
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
Transient reinforcing effects of phenylisopropylamine and indolealkylamine hallucinogens in rhesus monkeys.
2004 Mar
Endogenous psychoactive tryptamines reconsidered: an anxiolytic role for dimethyltryptamine.
2005
Phytochemical analyses of Banisteriopsis caapi and Psychotria viridis.
2005 Jun
NMR spectral assignments of a new chlorotryptamine alkaloid and its analogues from Acacia confusa.
2007 Apr
DMT at fifty.
2007 Dec
Halogenated solvent interactions with N,N-dimethyltryptamine: formation of quaternary ammonium salts and their artificially induced rearrangements during analysis.
2008 Jul 4
Indolealkylamines: biotransformations and potential drug-drug interactions.
2008 Jun
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
Predicting new molecular targets for known drugs.
2009 Nov 12
The chemical basis of pharmacology.
2010 Dec 7
Neuronal correlates of visual and auditory alertness in the DMT and ketamine model of psychosis.
2010 Oct
The hallucinogenic world of tryptamines: an updated review.
2015 Aug
Patents

Patents

JP4641942B2
8
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:09:05 GMT 2023
Edited
by admin
on Fri Dec 15 17:09:05 GMT 2023
Record UNII
WUB601BHAA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIMETHYLTRYPTAMINE
MART.   WHO-DD  
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
MI  
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
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
WIKIPEDIA TiHKAL
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
DEA NO. 7435
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
Code System Code Type Description
WIKIPEDIA
DIMETHYLTRYPTAMINE
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-508-4
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID60110053
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
NSC
63795
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
CAS
61-50-7
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
PUBCHEM
6089
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
CHEBI
28969
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
FDA UNII
WUB601BHAA
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
MERCK INDEX
m4558
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY Merck Index
HSDB
8017
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
SMS_ID
100000126254
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
INCB IDS CODE
PD 004
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
DRUG BANK
DB01488
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
EVMPD
SUB33250
Created by admin on Fri Dec 15 17:09:05 GMT 2023 , Edited by admin on Fri Dec 15 17:09:05 GMT 2023
PRIMARY
Related Record Type Details
5-HYDROXYTRYPTAMINE RECEPTOR 2A
TARGET->PARTIAL AGONIST
Ki
Structure of DIMETHYLTRYPTAMINE FUMARATE
SALT/SOLVATE -> PARENT
PSYCHOTRIA VIRIDIS LEAF
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
5-HYDROXYTRYPTAMINE RECEPTOR 1A
TARGET -> AGONIST
AGONIST
Ki
PSYCHOTRIA VIRIDIS WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
5-HYDROXYTRYPTAMINE RECEPTOR 2C
TARGET -> AGONIST
Ki
AMINE OXIDASE (FLAVIN-CONTAINING) A
METABOLIC ENZYME -> SUBSTRATE
MAJOR
5-HYDROXYTRYPTAMINE RECEPTOR 2A
TARGET -> AGONIST
all of the tryptamines, including DMT but with the exception of psilocin, were more potent agonists at the 5-HT2A receptor than LSD in the assay that was used in the present study. LSD and psilocin were 5-HT2A receptor partial agonists, with 28% and 16% activation efficacy, respectively, whereas all of the other compounds presented higher 5-HT2A receptor activation efficacies (up to >80% for DiPT and 5-MeO-MiPT). DMT has 40 maximal receptor activation.
EC50
Structure of DIMETHYLTRYPTAMINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of Dimethyltryptamine N-oxide
METABOLITE -> PARENT
Structure of INDOLEACETIC ACID
METABOLITE INACTIVE -> PARENT
Related Record Type Details
Structure of DIMETHYLTRYPTAMINE
ACTIVE MOIETY
NIH
NCATS
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