Chemicals and Drugs

Bufotenin

A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic.

Chemical Identity

Chemical Information

Molecular Formula
C12H16N2O
Molecular Weight
204.27 g/mol
CAS Registry No.
487-93-4
IUPAC Name
3-[2-(dimethylamino)ethyl]-1H-indol-5-ol
InChIKey
VTTONGPRPXSUTJ-UHFFFAOYSA-N
SMILES
CN(C)CCC1=CNC2=C1C=C(C=C2)O
MeSH Unique ID
D002027
Source
PubChem CID 10257

MeSH Record

Classification

Broader headings

Narrower headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

8 entry terms
  • 5-Hydroxy-N,N-dimethyltryptamine
  • Bufotenine
  • Dimethylserotonin
  • Mappin
  • Mappine
  • N,N-Dimethyl-5-hydroxytryptamine
  • 5 Hydroxy N,N dimethyltryptamine
  • N,N Dimethyl 5 hydroxytryptamine

MeSH Record

Aspects Covered

28 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, physiology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

Indexing Annotation

/biosyn permitted if by toads, mushrooms, etc.

MeSH Record

History Note

91(75); was see under SEROTONIN 1975-90; was see under HALLUCINOGENS 1966-74

MeSH Hierarchy

Tree Numbers

  1. D03w.633.100.473.914w.237w.150w
  2. D03w.633.100.473.914w.814w.150w
  3. D20.888w.033.163w
  4. D23.946w.833w.033.163w

AMA Style

References

  1. National Library of Medicine. Bufotenin. Medical Subject Headings (MeSH). 2026. Unique ID D002027. http://id.nlm.nih.gov/mesh/2026/D002027
  2. Bufotenin. In: Wikipedia. https://en.wikipedia.org/wiki/Bufotenin
  3. Bufotenin. In: Wikidata. https://www.wikidata.org/wiki/Q408915
  4. Bufotenin. In: PubChem Compound. CID 10257. https://pubchem.ncbi.nlm.nih.gov/compound/10257