Dronabinol

Dronabinol
Clinical data
Trade names	Marinol, Syndros
Other names	(−)-trans-Δ9-tetrahydrocannabinol
License data	US FDA: Dronabinol;
Dependence; liability	Physical: Low ; Psychological: Low–moderate
Addiction; liability	Relatively low
Routes of; administration	By mouth
Drug class	Cannabinoid
ATC code	A04AD10 (WHO) ;
Legal status
Legal status	US: Schedule II as Syndros, Schedule III as Marinol;
Pharmacokinetic data
Bioavailability	POTooltip Oral administration: 6–20%
Onset of action	PO: 0.5–1 hour
Elimination half-life	25–36 hours
Duration of action	PO: 4–6 hours
Identifiers
	IUPAC name (6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol;
CAS Number	1972-08-3 ;
PubChem CID	16078;
IUPHAR/BPS	2424;
DrugBank	DB00470 ;
ChemSpider	15266 ;
UNII	7J8897W37S;
KEGG	D00306 ;
ChEBI	CHEBI:66964 ;
ChEMBL	ChEMBL465 ;
Chemical and physical data
Formula	C21H30O2
Molar mass	314.469 g·mol−1
3D model (JSmol)	Interactive image;
Specific rotation	−152° (ethanol)
Boiling point	155–157 °C (311–315 °F) 0.05mmHg, 157–160°C @ 0.05mmHg
Solubility in water	0.0028 mg/mL (23 °C)
	SMILES CCCCCc1cc(c2c(c1)OC([C@H]3[C@H]2C=C(CC3)C)(C)C)O;
	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 ; Key:CYQFCXCEBYINGO-IAGOWNOFSA-N ;

Dronabinol (INNTooltip International Nonproprietary Name), sold under the brand names Marinol and Syndros, is the generic name for the molecule of (−)-trans-Δ⁹-tetrahydrocannabinol (THC) in the pharmaceutical context. It has indications as an appetite stimulant, antiemetic, and sleep apnea reliever and is approved by the US Food and Drug Administration (FDA) as safe and effective for HIV/AIDS-induced anorexia and chemotherapy-induced nausea and vomiting.

Dronabinol is the principal psychoactive constituent enantiomer form, (−)-trans-Δ⁹-tetrahydrocannabinol, found in Cannabis sativa L. plants, but can also be synthesized in laboratory. Dronabinol does not include any other tetrahydrocannabinol (THC) isomers or any cannabidiol (CBD).