CHEBI:8613 - psilocin

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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
Monoisotopic Mass 204.126
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 phenols (CHEBI:33853)
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
HMDB0042000 HMDB
Psilocin Wikipedia
View more database links
Registry Numbers Types Sources
160503 Reaxys Registry Number Reaxys
160503 Beilstein Registry Number Beilstein
520-53-6 CAS Registry Number ChemIDplus
520-53-6 CAS Registry Number NIST Chemistry WebBook
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Last Modified
26 October 2017