Structure via PubChem · Public domain (PubChem)
psilocin
Sign in to saveAlso 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
Research
426 papers- Metabolism of psilocybin and psilocin: clinical and forensic toxicological relevance.Drug metabolism reviews · 2017
- Psychedelic effects of psilocybin correlate with serotonin 2A receptor occupancy and plasma psilocin levels.Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology · 2019
- Psilocybin and psilocin regulate microglial immunomodulation and support neuroplasticity via serotonergic and AhR signaling.International immunopharmacology · 2025
- Psilocybin: from ancient magic to modern medicine.The Journal of antibiotics · 2020
- Psilocybin treatment extends cellular lifespan and improves survival of aged mice.npj aging · 2025
via PubMed
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 sectionsContents
- 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.