bufotenine

Also known as 5-OH-DMT, dimethylserotonin, DM5-HT, N,N-dimethyl-5-HT, N,N-dimethylserotonin, Bufotenin, 3-[beta-(dimethylamino)ethyl]-5-hydroxyindole, 5-hydroxy-N,N-dimethyltryptamine

Bufotenin, also known as dimethylserotonin or as '5-hydroxy-N,N-dimethyltryptamine (5-HO-DMT'), is a serotonergic psychedelic of the tryptamine family. It is a derivative of the psychedelic dimethyltryptamine (DMT) and of the neurotransmitter serotonin (5-hydroxytryptamine; 5-HT). The compound is an alkaloid found in some species of mushrooms, plants, and toads. It is also found naturally in the human body in small amounts. Bufotenin, for instance derived from the trees Anadenanthera colubrina and Anadenanthera peregrina, has a long history of entheogenic use as a snuff in South America.

Key facts

Drug.Watchedfields: verified
Drug.verifiedrevid: 443669819
Drug.image: Bufotenin2DACS.svg
Drug.image_class: skin-invert-image
Drug.width: 225px
Drug.image2: Bufotenin-3d-sticks.png
Drug.image_class2: bg-transparent
Drug.width2: 225px
Drug.legal_AU: S9
Drug.legal_CA: Unscheduled
Drug.legal_DE: NpSG
Drug.legal_UK: Class A
Drug.legal_US: Schedule I
Drug.legal_status: Illegal in Sweden
Drug.routes_of_administration: Oral, intranasal/insufflation, inhalation, sublingual, rectal, intravenous
Drug.class: Serotonergic psychedelic; Hallucinogen; Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist
Drug.bioavailability: Weakly active (with or without )
Drug.metabolism: Deamination via and conjugation (glucuronidation, sulfation)

via Wikipedia infobox

Chemical data

Formula: C12H16N2O
Molecular weight: 204.27 g/mol
IUPAC name: 3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
SMILES: CN(C)CCC1=CNC2=C1C=C(C=C2)O
InChIKey: VTTONGPRPXSUTJ-UHFFFAOYSA-N
XLogP: 1.2
Polar surface area: 39.3 Å²
H-bond donors: 2
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

676 papers

Bufotenine: toward an understanding of possible psychoactive mechanisms.Journal of psychoactive drugs · 2000
Bufotenine use in drug facilitated sexual assult.Medicina clinica · 2022
Bufotenine esters.Journal of medicinal chemistry · 1979
In vitro effects of bufotenine against RNA and DNA viruses.Brazilian journal of microbiology : [publication of the Brazilian Society for Microbiology] · 2021
Bufotenine reconsidered.Acta psychiatrica Scandinavica · 1985

via PubMed

Wikidata facts

Mass: 204.126263

Show 3 more facts

chemical formula: C₁₂H₁₆N₂O
Commons category: Bufotenin
canonical SMILES: CN(C)CCC1=CNC2=C1C=C(C=C2)O

Sources (2)

via Wikidata · CC0

~28 min read

Article

39 sections

Contents

Use and effects
Fabing & Hawkins (1955)
Isbell (1956)
Turner & Merlis (1959)
Hofmann (1963)
McLeod and Sitaram (1985)
Shulgin (1997)
Ott (2001)
Morris (2020s)
Side effects
Overdose
Interactions
Pharmacology
Pharmacodynamics
Pharmacokinetics
Chemistry
Properties
Synthesis
Analogues and derivatives
Natural occurrence
Toads
''Anadenanthera'' seeds
Other sources
Occurrence in humans
Association with psychiatric conditions
History
Society and culture
Names
Recreational use
Legal status
Australia
Canada
Sweden
United Kingdom
United States
Research
See also
References
External links

The name bufotenin originates from the toad genus Bufo, which includes several species of psychoactive toads, most notably Incilius alvarius (formerly Bufo alvarius), that secrete bufotoxins from their parotoid glands. However, Bufo and related species like Incilius alvarius contain only trace amounts of bufotenin, with their major active component instead being 5-MeO-DMT. In addition to DMT and serotonin, bufotenin is similar in chemical structure to other psychedelics such as 5-MeO-DMT and psilocin (4-HO-DMT). These compounds also occur in some of the same fungus, plant, and animal species as bufotenin.