DMT

Also known as N,N-dimethyltryptamine, 3-(2-dimethylaminoethyl)indole, N,N-dimethyl-1H-indole-3-ethylamine, 3-[2-(dimethylamino)ethyl]indole, 2-(3-indolyl)ethyldimethylamine, Indolalkylamine der, 2-(1H-Indol-3-yl)-N,N-dimethylethanamine (ACD/Name 4.0)

Dimethyltryptamine (DMT), also known as '''N,N-dimethyltryptamine (N,N-DMT'''), is a serotonergic hallucinogen and investigational drug of the tryptamine family that occurs naturally in many plants and animals. DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.

OverviewAI-generated

Dimethyltryptamine is a chemical compound with the formula C₁₂H₁₆N₂. Its IUPAC name is 2-(1H-indol-3-yl)-N,N-dimethylethanamine. The substance has a mass of 188.131349 and a density of 1.076. It melts at 47 and decomposes at 49. The boiling point is 332.12, and the pKa is 8.68.

Chemical properties include an xlogp of 2.5 and a topological polar surface area of 19. The molecule contains one hydrogen bond donor and one hydrogen bond acceptor, with a charge of 0. The canonical SMILES notation is CN(C)CCC1=CNC2=CC=CC=C21.

The compound is referenced by 2,999 other encyclopedia articles. A PubMed search for dimethyltryptamine yields a count of 1446.

Synthesized by Vinony from 22 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.width2: 200px
Drug.verifiedrevid: 623685269
Drug.Watchedfields: changed
Drug.drug_name: Dimethyltryptamine
Drug.image: DMT.svg
Drug.image_class: skin-invert-image
Drug.width: 175px
Drug.image2: Dimethyltryptamine molecule ball.png
Drug.image_class2: bg-transparenT
Drug.receptors: At least 13 receptors (e.g., serotonin, sigma, trace amine)
Drug.precursor: Tryptophan
Drug.source_tissues: Central nervous system (exact source tissues are not fully established)
Drug.target_tissues: Central nervous system
Drug.routes_of_administration: Oral (with ), inhalation (smoking or vaping), intramuscular, subcutaneous, intravenous (bolus or infusion)
Drug.class: Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Drug.dependency_liability: None or very low
Drug.addiction_liability: None or very low
Drug.ATC_prefix: None

via Wikipedia infobox

Chemical data

Formula: C12H16N2
Molecular weight: 188.27 g/mol
IUPAC name: 2-(1H-indol-3-yl)-N,N-dimethylethanamine
SMILES: CN(C)CCC1=CNC2=CC=CC=C21
InChIKey: DMULVCHRPCFFGV-UHFFFAOYSA-N
XLogP: 2.5
Polar surface area: 19 Å²
H-bond donors: 1
H-bond acceptors: 1
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule
Indications: stroke, major depressive disorder, depressive disorder

via ChEMBL · EBI

Research

1,446 papers

N,N-dimethyltryptamine and the pineal gland: Separating fact from myth.Journal of psychopharmacology (Oxford, England) · 2018
Dimethyltryptamine: Endogenous Role and Therapeutic Potential.Journal of psychoactive drugs · 2019
N,N-dimethyltryptamine and Amazonian ayahuasca plant medicine.Human psychopharmacology · 2022
Neuropharmacology of N,N-dimethyltryptamine.Brain research bulletin · 2016
Ayahuasca and Dimethyltryptamine Adverse Events and Toxicity Analysis: A Systematic Thematic Review.International journal of toxicology · 2024

via PubMed

Wikidata facts

Has part: hydrogen
Mass: 188.131349
Image: D-Tryp.jpg

Show 10 more facts

Commons category: Dimethyltryptamine
found in taxon: Phlegmariurus phlegmaria
chemical formula: C₁₂H₁₆N₂
density: 1.076
canonical SMILES: CN(C)CCC1=CNC2=CC=CC=C21
boiling point: 332.12
melting point: 47
subject has role: serotonin receptor agonists
decomposition point: 49
pKa: 8.68

Sources (4)

via Wikidata · CC0

Article · Svenska

DMT, N,N-Dimetyltryptamin alternativt N,N-dimetyl-(2-indolyl-(3)-etyl)amin, summaformel C12H16N2, är en kraftigt psykoaktiv enteogen ur klassen tryptaminer. DMT kan enbart intas genom parenterala vägar, det vill säga rökning eller injektion, utan kombinerat intag av MAO-hämmare. Om det intas oralt bryter kroppen ned det till fullo och drogens effekt uteblir. För att förhindra det kan man samtidigt inta en hämmare för det enzym som bryter ned drogen, en MAO-hämmare. I Sydamerika använder urbefolkningen en brygd, ayahuasca, gjord på två olika växter där den ena innehåller DMT och den andra en MAO-hämmare. Vid korrekt intag av drogen kan effekten vara mycket intensiv och ge starka upplevelser, däribland intensiva visioner eller hallucinationer där användaren helt förflyttas till en värld utan kontakt med verkligheten, något som kan leda till otrevliga upplevelser och djup rädsla, men även stark eufori och upplevelser av andlig mening. DMT framställdes först helt syntetiskt 1931. Länge trodde man att det var en helt syntetisk drog, tills man efter ungefär 20 år även hittade det i olika växter i naturen. Ämnet bildas vid normal metabolism och finns naturligt i människokroppen. I Norden går det att utvinna drogen ur rörflen, ett vanligt förekommande gräs. Den snarlika drogen DET är etylanalogen av DMT. DMT är narkotikaklassat och ingår i förteckning P I i 1971 års psykotropkonvention, samt i förteckning I i Sverige.

Abstract from DBpedia / Wikipedia · CC BY-SA