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psilocin

Structure via PubChem · Public domain (PubChem)

EntityQ409150· pop 32· linked from 2,254 articles

Also known as 4-HO-DMT, N,N-dimethyl-4-hydroxytryptamine, 4-hydroxy-N,N-dimethyltryptamine, 4-OH-DMT, Psilocine, 3-(2-(Dimethylamino)ethyl)indol-4-ol, Psilotsin

Psilocin, also known as '4-hydroxy-N,N-dimethyltryptamine (4-HO-DMT'), is a psychedelic drug and fungal alkaloid of the tryptamine and 4-hydroxytryptamine families. Along with its phosphate ester psilocybin, it is found in most species of psilocybin-containing mushrooms, such as Psilocybe cubensis and Psilocybe mexicana, and is the compound responsible for their hallucinogenic effects, although concentrations of psilocin are variably lower than those of psilocybin. The drug is taken orally and its effects include perceptual changes and visual effects, emotional changes, ego dissolution, time d

Key facts

Drug.Verifiedfields
verified
Drug.Watchedfields
verified
Drug.verifiedrevid
458622491
Drug.image
Psilocine skeletal formula.svg
Drug.image_class
skin-invert-image
Drug.width
175px
Drug.alt
Skeletal formula
Drug.image2
Psilocin-3D-balls.png
Drug.image_class2
bg-transparent
Drug.width2
200px
Drug.alt2
Ball-and-stick model
Drug.routes_of_administration
Oral, intravenous
Drug.class
Serotonergic psychedelic; Hallucinogen; Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist
Drug.ATC_prefix
None
Drug.legal_AU
S9
Drug.legal_BR
F2
Drug.legal_CA
Schedule III
Drug.legal_UK
Class A

via Wikipedia infobox

Chemical data

Formula
C12H16N2O
Molecular weight
204.27 g/mol
IUPAC name
3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
SMILES
CN(C)CCC1=CNC2=C1C(=CC=C2)O
InChIKey
SPCIYGNTAMCTRO-UHFFFAOYSA-N
XLogP
2.1
Polar surface area
39.3 Ų
H-bond donors
2
H-bond acceptors
2
Formal charge
0

via PubChem

Wikidata facts

Mass
204.126
Show 3 more facts
chemical formula
C₁₂H₁₆N₂O
Commons category
Psilocin
canonical SMILES
CN(C)CCC1=CNC2=C1C(=CC=C2)O
Sources (2)

via Wikidata · CC0

~12 min read

Article

24 sections
Contents
  • Use and effects
  • Contraindications
  • Side effects
  • Overdose
  • Interactions
  • Pharmacology
  • Pharmacodynamics
  • Pharmacokinetics
  • Chemistry
  • Synthesis
  • Stability
  • Analogues
  • History
  • Society and culture
  • Legal status
  • United Nations
  • Australia
  • Canada
  • Russia
  • United States
  • Research
  • See also
  • References
  • External links

Psilocin, also known as '4-hydroxy-N,N-dimethyltryptamine (4-HO-DMT'), is a psychedelic drug and fungal alkaloid of the tryptamine and 4-hydroxytryptamine families. Along with its phosphate ester psilocybin, it is found in most species of psilocybin-containing mushrooms, such as Psilocybe cubensis and Psilocybe mexicana, and is the compound responsible for their hallucinogenic effects, although concentrations of psilocin are variably lower than those of psilocybin. The drug is taken orally and its effects include perceptual changes and visual effects, emotional changes, ego dissolution, time dilation, and mystical experiences, among others. Psilocybin, as well as synthetic acyl esters such as 4-AcO-DMT (psilacetin; O-acetylpsilocin) and 4-PrO-DMT (O-propionylpsilocin), are prodrugs of psilocin and have similar properties and effects.

Psilocin acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor among others. The drug produces its hallucinogenic effects specifically via activation of the serotonin 5-HT2A receptor. However, other serotonin receptors, such as the serotonin 5-HT1A and 5-HT2C receptors, may also contribute to its effects. Notable analogues of psilocin include dimethyltryptamine (DMT), its positional isomer bufotenin (5-HO-DMT), its higher homologue 4-HO-MET (metocin), and others.

Gallery (3)

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