psilocin (CHEBI:8613)

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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

Average Mass

204.26820

Monoisotopic Mass

204.12626

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
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

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.

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) psilocin (CHEBI:8613) is conjugate base of psilocinium (CHEBI:193059)

Incoming	psilocybin (CHEBI:8614) has functional parent psilocin (CHEBI:8613) psilocinium (CHEBI:193059) is conjugate acid of 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

Last Modified

26 October 2017