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CHEBI:66964 - Δ9-tetrahydrocannabinol

ChEBI IDCHEBI:66964
ChEBI NameΔ9-tetrahydrocannabinol
Stars
ASCII NameDelta(9)-tetrahydrocannabinol
DefinitionA diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.
Secondary ChEBI IDCHEBI:4716
Last Modified22 February 2017
SubmitterKAX
DownloadsMolfile
FormulaC21H30O2
Net Charge0
Average Mass314.469
Monoisotopic Mass314.22458
SMILES[H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)Oc1cc(CCCCC)cc(O)c12
InChIInChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
InChIKeyCYQFCXCEBYINGO-IAGOWNOFSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Cannabis sativa (ncbitaxon:3483) aerial part (BTO:0001658) PubMed (21902175) Acetone extract of Dried, powdered and heated flowered aerial parts
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
epitope  The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
cannabinoid receptor agonist  An agonist that binds to and activates cannabinoid receptors.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
cannabinoid receptor agonist  An agonist that binds to and activates cannabinoid receptors.
cannabinoid receptor agonist  An agonist that binds to and activates cannabinoid receptors.
Applications:
hallucinogen  Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
ChEBI Ontology
Outgoing Relation(s)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role cannabinoid receptor agonist (CHEBI:67072)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role epitope (CHEBI:53000)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role hallucinogen (CHEBI:35499)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role metabolite (CHEBI:25212)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role non-narcotic analgesic (CHEBI:35481)
Δ9-tetrahydrocannabinol (CHEBI:66964) is a benzochromene (CHEBI:38920)
Δ9-tetrahydrocannabinol (CHEBI:66964) is a diterpenoid (CHEBI:23849)
Δ9-tetrahydrocannabinol (CHEBI:66964) is a phytocannabinoid (CHEBI:67196)
Δ9-tetrahydrocannabinol (CHEBI:66964) is a polyketide (CHEBI:26188)
Incoming Relation(s)
11-hydroxy-Δ9-tetrahydrocannabinol (CHEBI:77270) has functional parent Δ9-tetrahydrocannabinol (CHEBI:66964)
11-nor-9-carboxy-Δ9-tetrahydrocannabinol (CHEBI:77273) has functional parent Δ9-tetrahydrocannabinol (CHEBI:66964)
IUPAC Name 
(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
INN  Source
dronabinolKEGG DRUG
Synonyms  Source
DronabinolKEGG COMPOUND
delta9-TetrahydrocannabinolKEGG COMPOUND
TetrahydrocannabinolKEGG COMPOUND
Δ1-tetrahydrocannabinolSUBMITTER
Δ9-THCSUBMITTER
DronabinolumChemIDplus
Brand Name  Source
SyndrosChEBI
UniProt Name  Source
Δ9-tetrahydrocannabinolUniProt
Manual XrefsDatabases
C06972KEGG COMPOUND
CPD-7172MetaCyc
TCIPDBeChem
D00306KEGG DRUG
DB00470DrugBank
TetrahydrocannabinolWikipedia
HMDB0041865HMDB
C00002675KNApSAcK
4109DrugCentral
Registry NumbersSources
Reaxys:4354308Reaxys
CAS:1972-08-3KEGG COMPOUND
CAS:1972-08-3ChemIDplus
CAS:1972-08-3NIST Chemistry WebBook
Citations