File:DMT.svg · Wikimedia Commons · See Wikimedia Commons
Dimethyltryptamin
Sign in to saveAlso known as DMT, 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)
halluzinogene chemische Verbindung
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 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
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
Article · Deutsch
N,N-Dimethyltryptamin, kurz DMT, ist ein halluzinogenes Tryptamin-Alkaloid. Es findet u. a. Anwendung als Psychedelikum bzw. Entheogen, indem es geraucht (als Freibase), geschnupft (als Yopo) oder injiziert (als Fumaratsalz) wird. Eine Wirkung bei peroraler Aufnahme (etwa als Ayahuasca) ist nur bei gleichzeitiger bzw. vorheriger Einnahme von Monoaminooxidase-Hemmern (kurz MAOH oder MAOI) möglich, da DMT sehr rasch (First-Pass-Effekt) vom körpereigenen Enzym Monoaminooxidase (Typ A) abgebaut wird. Dimethyltryptamin wurde erstmals im Jahre 1931 von dem kanadischen Chemiker (1901–1977) synthetisiert.
Abstract from DBpedia / Wikipedia · CC BY-SA