CHEBI:8614 - psilocybin

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ChEBI Name psilocybin
ChEBI ID CHEBI:8614
Definition A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional phosphoryloxy substituent at position 4. The major hallucinogenic alkaloid isolated 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 C12H17N2O4P
Net Charge 0
Average Mass 284.24810
Monoisotopic Mass 284.093
InChI InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)
InChIKey QVDSEJDULKLHCG-UHFFFAOYSA-N
SMILES CN(C)CCc1c[nH]c2cccc(OP(O)(O)=O)c12
Metabolite of Species Details
Psilocybe (NCBI:71950) See: PubMed
Roles Classification
Biological Role(s): 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.
(via alkaloid )
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing psilocybin (CHEBI:8614) has functional parent psilocin (CHEBI:8613)
psilocybin (CHEBI:8614) has role fungal metabolite (CHEBI:76946)
psilocybin (CHEBI:8614) has role hallucinogen (CHEBI:35499)
psilocybin (CHEBI:8614) has role prodrug (CHEBI:50266)
psilocybin (CHEBI:8614) has role serotonergic agonist (CHEBI:35941)
psilocybin (CHEBI:8614) is a organic phosphate (CHEBI:25703)
psilocybin (CHEBI:8614) is a tertiary amino compound (CHEBI:50996)
psilocybin (CHEBI:8614) is a tryptamine alkaloid (CHEBI:48274)
psilocybin (CHEBI:8614) is conjugate acid of psilocybin(1−) (CHEBI:139072)
Incoming psilocybin(1−) (CHEBI:139072) is conjugate base of psilocybin (CHEBI:8614)
IUPAC Name
3-[2-(dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate
INNs Sources
psilocibina ChemIDplus
psilocybine ChemIDplus
psilocybinum ChemIDplus
Synonyms Sources
3-(2-(Dimethylamino)ethyl)-1H-indol-4-ol dihydrogen phosphate ester ChemIDplus
3-(2-Dimethylaminoethyl)indol-4-yl dihydrogen phosphate ChemIDplus
4-phosphoryloxy-N,N-dimethyltryptamine NIST Chemistry WebBook
Indocybin ChemIDplus
O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine NIST Chemistry WebBook
psilocin phosphate ester ChemIDplus
Psilocybin KEGG COMPOUND
Psilocybine KEGG COMPOUND
Database Links Databases
C07576 KEGG COMPOUND
Psilocybin Wikipedia
View more database links
Registry Numbers Types Sources
273158 Beilstein Registry Number Beilstein
273158 Reaxys Registry Number Reaxys
520-52-5 CAS Registry Number KEGG COMPOUND
520-52-5 CAS Registry Number NIST Chemistry WebBook
520-52-5 CAS Registry Number ChemIDplus
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Last Modified
27 October 2017