CHEBI:8614 - psilocybin

ChEBI IDCHEBI:8614
ChEBI Namepsilocybin
Stars
DefinitionA 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").
Last Modified27 October 2017
DownloadsMolfile
FormulaC12H17N2O4P
Net Charge0
Average Mass284.252
Monoisotopic Mass284.09259
SMILESCN(C)CCc1cnc2cccc(OP(=O)(O)O)c12
InChIInChI=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)
InChIKeyQVDSEJDULKLHCG-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Psilocybe (ncbitaxon:71950) - PubMed (25007546)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
antibacterial drug  A drug used to treat or prevent bacterial infections.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
anxiolytic drug  Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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.
appetite enhancer  A drug which increases appetite.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
hallucinogen  Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.
vulnerary  A drug used in treating and healing of wounds.
antipsychotic agent  Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
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.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
antibacterial drug  A drug used to treat or prevent bacterial infections.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
ChEBI Ontology
Outgoing Relation(s)
psilocybin (CHEBI:8614) has functional parent psilocin (CHEBI:8613)
psilocybin (CHEBI:8614) has role analgesic (CHEBI:35480)
psilocybin (CHEBI:8614) has role antibacterial drug (CHEBI:36047)
psilocybin (CHEBI:8614) has role antidepressant (CHEBI:35469)
psilocybin (CHEBI:8614) has role antineoplastic agent (CHEBI:35610)
psilocybin (CHEBI:8614) has role antipsychotic agent (CHEBI:35476)
psilocybin (CHEBI:8614) has role anxiolytic drug (CHEBI:35474)
psilocybin (CHEBI:8614) has role appetite enhancer (CHEBI:50779)
psilocybin (CHEBI:8614) has role fungal metabolite (CHEBI:76946)
psilocybin (CHEBI:8614) has role geroprotector (CHEBI:176497)
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) has role vulnerary (CHEBI:73336)
psilocybin (CHEBI:8614) is a aryl phosphate (CHEBI:36943)
psilocybin (CHEBI:8614) is a organic molecular entity (CHEBI:50860)
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 Relation(s)
psilocybin(1−) (CHEBI:139072) is conjugate base of psilocybin (CHEBI:8614)
IUPAC Name 
3-[2-(dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate
INNs  Source
psilocibinaChemIDplus
psilocybineChemIDplus
psilocybinumChemIDplus
Synonyms  Source
3-(2-(Dimethylamino)ethyl)-1H-indol-4-ol dihydrogen phosphate esterChemIDplus
3-(2-Dimethylaminoethyl)indol-4-yl dihydrogen phosphateChemIDplus
4-phosphoryloxy-N,N-dimethyltryptamineNIST Chemistry WebBook
COMP-360ChEMBL
COMP360ChEMBL
CY 39ChEMBL
Manual XrefsDatabases
C07576KEGG COMPOUND
PsilocybinWikipedia
Registry NumbersSources
Reaxys:273158Reaxys
CAS:520-52-5NIST Chemistry WebBook
CAS:520-52-5ChemIDplus
CAS:520-52-5KEGG COMPOUND
Citations