Δ9-tetrahydrocannabinol   

GtoPdb Ligand ID: 2424

Abbreviated name: THC
Synonyms: Δ9-THC | Abbott 40566 | delta9-THC | Marinol® | tetrahydrocannabinol
Δ9-tetrahydrocannabinol is an approved drug (FDA (1985))
Comment: Δ9-tetrahydrocannabinol is the active ingredient found in cannabis plants (Cannabis sativa). Dronabinol is the INN for the pure, synthetically produced (-)-trans9-tetrahydrocannabinol isomer of tetrahydrocannabinol (shown here).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 0
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 29.46
Molecular weight 314.22
XLogP 6.47
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCCCCc1cc(O)c2c(c1)OC(C1C2C=C(C)CC1)(C)C
Isomeric SMILES CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2C=C(C)CC1)(C)C
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
InChI Key CYQFCXCEBYINGO-IAGOWNOFSA-N
No information available.
Summary of Clinical Use
Used in the treatment of anorexia in patients with AIDS, and treatment of nausea and vomiting associated with cancer chemotherapy in patients who have not reposnded to conventional antiemetic treatments. Clinical formulations of dronabinol are available in capsule form (Marinol®), and as of July 2016 (with US FDA apporval), as an oral solution (Syndros®).
Tetrahydrocannabinol, in a drug mixture containing cannabidiol (Sativex®, administered as an oromucosal spray), may also be used (in countries including the UK, Spain, Italy and Germany) to improve moderate to severe spastic symptoms in patients with multiple sclerosis (MS), and who have responded poorly to other anti-spasticity medications.
Mechanism Of Action and Pharmacodynamic Effects
The mechanism of action of THC is not completely understood. CB1 receptor agonist activity inhibits cyclic AMP production in areas of the central nervous system that mediate pain, memory, and other key functions, and is at least partially responsible for the physiological effects of cannabinoids. In addition, cannabidiol has been shown to stimulate vanilloid pain receptors (TRPVs), and to modulate cellular uptake and enzymatic hydrolysis of endogenous anandamide, effects which may contribute towards the pharmacological effects of cannabidiol [3].
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