CHEBI:8613 - psilocin

Main ChEBI Ontology Automatic Xrefs
ChEBI Name psilocin
ChEBI ID CHEBI:8613
Definition A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional hydroxy substituent at position 4. A hallucinogenic alkaloid isolated in trace amounts from Psilocybe mushrooms (also known as Teonanácatl or "magic mushrooms").
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C12H16N2O
Net Charge 0
Average Mass 204.26820
InChI InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3
InChIKey SPCIYGNTAMCTRO-UHFFFAOYSA-N
SMILES CN(C)CCc1c[nH]c2cccc(O)c12
Roles Classification
Biological Role(s): serotonergic agonist
An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
drug metabolite

metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): hallucinogen
Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.
serotonergic agonist
An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
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ChEBI Ontology
Outgoing psilocin (CHEBI:8613) has functional parent N,N-dimethyltryptamine (CHEBI:28969)
psilocin (CHEBI:8613) has role drug metabolite (CHEBI:49103)
psilocin (CHEBI:8613) has role fungal metabolite (CHEBI:76946)
psilocin (CHEBI:8613) has role hallucinogen (CHEBI:35499)
psilocin (CHEBI:8613) has role human xenobiotic metabolite (CHEBI:76967)
psilocin (CHEBI:8613) has role serotonergic agonist (CHEBI:35941)
psilocin (CHEBI:8613) is a hydroxyindoles (CHEBI:84729)
psilocin (CHEBI:8613) is a tertiary amino compound (CHEBI:50996)
psilocin (CHEBI:8613) is a tryptamine alkaloid (CHEBI:48274)
Incoming psilocybin (CHEBI:8614) has functional parent psilocin (CHEBI:8613)
IUPAC Name
3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
Synonyms Sources
3-(2-(Dimethylamino)ethyl)indol-4-ol HMDB
4-hydroxy-N,N-dimethyltryptamine ChemIDplus
4-OH-DMT ChEBI
N,N-dimethyl-4-hydroxytryptamine NIST Chemistry WebBook
Psilocin KEGG COMPOUND
Psilocine HMDB
Psilotsin HMDB
Database Links Databases
C00001427 KNApSAcK
C08312 KEGG COMPOUND
HMDB42000 HMDB
Psilocin Wikipedia
View more database links
Registry Numbers Types Sources
160503 Beilstein Registry Number Beilstein
160503 Reaxys Registry Number Reaxys
520-53-6 CAS Registry Number ChemIDplus
520-53-6 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
21820980 PubMed citation CiteXplore
22138681 PubMed citation CiteXplore
23183899 PubMed citation CiteXplore
23851905 PubMed citation CiteXplore
24413570 PubMed citation CiteXplore
24904332 PubMed citation CiteXplore
4040953 PubMed citation CiteXplore
7194879 PubMed citation CiteXplore
Last Modified
09 February 2015