Delta(9)-tetrahydrocannabinol (CHEBI:66964)

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ChEBI Name	Δ⁹-tetrahydrocannabinol

ChEBI ID	CHEBI:66964

ChEBI ASCII Name	Delta(9)-tetrahydrocannabinol

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	KAX

Secondary ChEBI IDs	CHEBI:4716

Supplier Information	ChemicalBook:CB6705020, eMolecules:518145, eMolecules:883971, ZINC000006661227

Download	Molfile XML SDF

Wikipedia	License
l-DOPA, also known as l-3,4-dihydroxyphenylalanine and used medically as levodopa, is made and used as part of the normal biology of some plants and animals, including humans. Humans, as well as a portion of the other animals that utilize l-DOPA, make it via biosynthesis from the amino acid l-tyrosine. l-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines. Furthermore, l-DOPA itself mediates neurotrophic factor release by the brain and CNS. In some plant families (of the order Caryophyllales), l-DOPA is the central precursor of a biosynthetic pathway that produces a class of pigments called betalains. l-DOPA can be manufactured and in its pure form is sold as a drug with the INNTooltip International Nonproprietary Name levodopa. Trade names include Sinemet, Pharmacopa, Atamet, and Stalevo. As a drug, it is used in the treatment of Parkinson's disease and dopamine-responsive dystonia, as well as restless leg syndrome. l-DOPA has a counterpart with opposite chirality, d-DOPA. As is true for many molecules, the human body produces only one of these isomers (the l-DOPA form). The enantiomeric purity of l-DOPA may be analyzed by determination of the optical rotation or by chiral thin-layer chromatography.
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Formula

C21H30O2

Net Charge

Average Mass

314.46170

Monoisotopic Mass

314.22458

InChI

InChI=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

InChIKey

CYQFCXCEBYINGO-IAGOWNOFSA-N

SMILES

[H][C@@]12CCC(C)=C[C@@]1([H])c1c(O)cc(CCCCC)cc1OC2(C)C

Metabolite of Species	Details
Cannabis sativa (NCBI:txid3483)	Found in aerial part (BTO:0001658). Acetone extract of Dried, powdered and heated flowered aerial parts See: PubMed

Roles Classification
Biological Role(s):	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. (via phytocannabinoid ) non-narcotic analgesic A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors. cannabinoid receptor agonist An agonist that binds to and activates cannabinoid receptors. (via cannabinoid )

Application(s):	non-narcotic analgesic A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors. hallucinogen Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.

ChEBI Ontology
Outgoing	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	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
dronabinol	KEGG DRUG

Synonyms	Sources
(-)-delta9-trans-Tetrahydrocannabinol	ChemIDplus
1-trans-delta-9-Tetrahydrocannabinol	ChemIDplus
3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,d)pyran-1-ol	ChemIDplus
6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol	NIST Chemistry WebBook
Δ¹-tetrahydrocannabinol	SUBMITTER
delta9-Tetrahydrocannabinol	KEGG COMPOUND
Δ⁹-tetrahydrocannabinol	UniProt
Δ⁹-THC	SUBMITTER
Dronabinol	KEGG COMPOUND
Dronabinolum	ChemIDplus
Tetrahydrocannabinol	KEGG COMPOUND

Brand Name	Source
Syndros	ChEBI

Last Modified

22 February 2017