Nabilone

Nabilone
	Top: (R,R)-(−)-nabilone,; Center: (S,S)-(+)-nabilone,; Bottom: Space-filling model of (R,R)-(−)-nabilone
Clinical data
Trade names	Cesamet, others
AHFS/Drugs.com	Monograph
MedlinePlus	a607048
Routes of; administration	By mouth
Drug class	Cannabinoid
ATC code	A04AD11 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled drug); CA: Schedule II; DE: Anlage III (Special prescription form required); UK: POM (Prescription only); US: Schedule II; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	20% after first-pass by the liver
Protein binding	similar to THC (±97%)
Elimination half-life	2 hours, with metabolites around 35 hours
Identifiers
	IUPAC name rel-(6aR,10aR)-1-Hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6,6a,7,8,10,10a-hexahydro-9H-benzo[c]chromen-9-one;
CAS Number	51022-71-0 ;
PubChem CID	5284592;
DrugBank	DB00486 ;
ChemSpider	4447641 ;
UNII	2N4O9L084N;
KEGG	D05099 ;
ChEMBL	ChEMBL947 ;
ECHA InfoCard	100.164.824
Chemical and physical data
Formula	C24H36O3
Molar mass	372.549 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C3CC[C@@H]1[C@H](c2c(OC1(C)C)cc(cc2O)C(C)(C)CCCCCC)C3;
	InChI InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3/t18-,19-/m1/s1 ; Key:GECBBEABIDMGGL-RTBURBONSA-N ;
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Nabilone, sold under the brand name Cesamet among others, is a synthetic cannabinoid with therapeutic use as an antiemetic and as an adjunct analgesic for neuropathic pain. It mimics tetrahydrocannabinol (THC) and hexahydrocannabinol (HHC), two compounds found naturally in the plant genus Cannabis.

The Food and Drug Administration (FDA) in the United States has approved nabilone solely for the treatment of chemotherapy-induced nausea/vomiting. In other countries, such as Canada, it is widely used as an adjunct therapy for chronic pain management. Numerous clinical trials and case studies have demonstrated modest effectiveness in fibromyalgia and multiple sclerosis.