CHEBI:8613 - psilocin

ChEBI IDCHEBI:8613
ChEBI Namepsilocin
Stars
DefinitionA 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").
Last Modified26 October 2017
DownloadsMolfile
FormulaC12H16N2O
Net Charge0
Average Mass204.273
Monoisotopic Mass204.12626
SMILESCN(C)CCc1cnc2cccc(O)c12
InChIInChI=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
InChIKeySPCIYGNTAMCTRO-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
human xenobiotic metabolite  Any human metabolite produced by metabolism of a xenobiotic compound in humans.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
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.
hallucinogen  Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
PsilocinKEGG COMPOUND
N,N-dimethyl-4-hydroxytryptamineNIST Chemistry WebBook
4-hydroxy-N,N-dimethyltryptamineChemIDplus
PsilotsinHMDB
3-(2-(Dimethylamino)ethyl)indol-4-olHMDB
PsilocineHMDB
Manual XrefsDatabases
C08312KEGG COMPOUND
C00001427KNApSAcK
HMDB0042000HMDB
PsilocinWikipedia
Registry NumbersSources
Reaxys:160503Reaxys
CAS:520-53-6KEGG COMPOUND
CAS:520-53-6NIST Chemistry WebBook
CAS:520-53-6ChemIDplus
Citations