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CHEBI:66964 - Δ9-tetrahydrocannabinol

Default Structure
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:
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
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.
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.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
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.
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:
antirheumatic drug  A drug used to treat rheumatoid arthritis.
antiemetic  A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
antipsychotic agent  Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
anti-anaemic agent  A compound which increases either the number of red cells or the amount of haemoglobin in the blood.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antispasmodic drug  A drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder.
hypoglycemic agent  A drug which lowers the blood glucose level.
appetite enhancer  A drug which increases appetite.
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.
hallucinogen  Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.
ChEBI Ontology
Outgoing Relation(s)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role analgesic (CHEBI:35480)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role anti-anaemic agent (CHEBI:75835)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role anti-HIV agent (CHEBI:64946)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role anti-inflammatory agent (CHEBI:67079)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role antidepressant (CHEBI:35469)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role antiemetic (CHEBI:50919)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role antineoplastic agent (CHEBI:35610)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role antipsychotic agent (CHEBI:35476)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role antirheumatic drug (CHEBI:35842)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role antispasmodic drug (CHEBI:53784)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role appetite enhancer (CHEBI:50779)
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 hypoglycemic agent (CHEBI:35526)
Δ9-tetrahydrocannabinol (CHEBI:66964) has role immunosuppressive agent (CHEBI:35705)
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
1-trans-delta-9-TetrahydrocannabinolChemIDplus
3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,d)pyran-1-olChemIDplus
6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-olNIST Chemistry WebBook
ABBOTT 40566ChEMBL
ABBOTT-40566ChEMBL
.delta.1-thcChEMBL
Brand Names  Source
Dronabinol component of ad-313ChEMBL
Dronabinol component of ad313ChEMBL
Dronabinol component of sci-110ChEMBL
SyndrosChEBI
UniProt Name  Source
Δ9-tetrahydrocannabinolUniProt
Manual XrefsDatabases
4109DrugCentral
C00002675KNApSAcK
C06972KEGG COMPOUND
CPD-7172MetaCyc
D00306KEGG DRUG
DB00470DrugBank
HMDB0041865HMDB
TCIPDBeChem
TetrahydrocannabinolWikipedia
Registry NumbersSources
Reaxys:4354308Reaxys
CAS:1972-08-3ChemIDplus
CAS:1972-08-3KEGG COMPOUND
CAS:1972-08-3NIST Chemistry WebBook
Citations