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: 9%
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	Oral: 6–20%
Onset of action	Oral: 0.5–1 hour
Elimination half-life	25–36 hours
Duration of action	Oral: 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^[4] and is approved by the U.S. Food and Drug Administration (FDA) as safe and effective for HIV/AIDS-induced anorexia and chemotherapy-induced nausea and vomiting.^[5]^[6]^[7]

Dronabinol is the principal psychoactive constituent enantiomer form, (−)-trans-Δ⁹-tetrahydrocannabinol, found in Cannabis sativa L. plants,^[8] but can also be synthesized in laboratory. Dronabinol does not include any other tetrahydrocannabinol (THC) isomers or any cannabidiol.

^ Gaoni Y, Mechoulam R (April 1964). "Isolation, Structure, and Partial Synthesis of an Active Constituent of Hashish". Journal of the American Chemical Society. 86 (8): 1646–47. Bibcode:1964JAChS..86.1646G. doi:10.1021/ja01062a046.
^ Adams R, Cain CK, McPhee WD, Wearn RB (August 1941). "Structure of Cannabidiol. XII. Isomerization to Tetrahydrocannabinols". Journal of the American Chemical Society. 63 (8): 2209–13. Bibcode:1941JAChS..63.2209A. doi:10.1021/ja01853a052.
^ Garrett ER, Hunt CA (July 1974). "Physiochemical properties, solubility, and protein binding of delta9-tetrahydrocannabinol". Journal of Pharmaceutical Sciences. 63 (7): 1056–64. doi:10.1002/jps.2600630705. PMID 4853640.
^ Schütz SG, Dunn A, Braley TJ, Pitt B, Shelgikar AV (June 2021). "New frontiers in pharmacologic obstructive sleep apnea treatment: A narrative review". Sleep Medicine Reviews. 57. Elsevier BV: 101473. doi:10.1016/j.smrv.2021.101473. PMID 33853035. S2CID 233242139. Initial rodent studies showed that injections of dronabinol, a synthetic form of delta-9-tetrahydrocannabinol, in the nodose ganglia suppressed serotonin induced reflex apneas and increased upper airway dilating muscle activity during sleep. Limited studies in humans with moderate-to-severe OSA have demonstrated significant reduction in AHI with dronabinol use.
^ "Marinol (Dronabinol)" (PDF). US Food and Drug Administration. September 2004. Retrieved 14 January 2018.
^ "Cannabis and Cannabinoids". National Cancer Institute. 2011-10-24. Retrieved 12 January 2014.
^ Badowski ME (September 2017). "A review of oral cannabinoids and medical marijuana for the treatment of chemotherapy-induced nausea and vomiting: a focus on pharmacokinetic variability and pharmacodynamics". Cancer Chemotherapy and Pharmacology. 80 (3): 441–449. doi:10.1007/s00280-017-3387-5. PMC 5573753. PMID 28780725.
^ "List of psychotropic substances under international control". International Narcotics Control Board. Retrieved 25 April 2018. This international non-proprietary name refers to only one of the stereochemical variants of delta-9-tetrahydrocannabinol, namely (−)-trans-delta-9-tetrahydrocannabinol

[1] Gaoni Y, Mechoulam R (April 1964). "Isolation, Structure, and Partial Synthesis of an Active Constituent of Hashish". Journal of the American Chemical Society. 86 (8): 1646–47. Bibcode:1964JAChS..86.1646G. doi:10.1021/ja01062a046.

[2] Adams R, Cain CK, McPhee WD, Wearn RB (August 1941). "Structure of Cannabidiol. XII. Isomerization to Tetrahydrocannabinols". Journal of the American Chemical Society. 63 (8): 2209–13. Bibcode:1941JAChS..63.2209A. doi:10.1021/ja01853a052.

[Garrett1974-3] Garrett ER, Hunt CA (July 1974). "Physiochemical properties, solubility, and protein binding of delta9-tetrahydrocannabinol". Journal of Pharmaceutical Sciences. 63 (7): 1056–64. doi:10.1002/jps.2600630705. PMID 4853640.

[Schütz_2021-4] Schütz SG, Dunn A, Braley TJ, Pitt B, Shelgikar AV (June 2021). "New frontiers in pharmacologic obstructive sleep apnea treatment: A narrative review". Sleep Medicine Reviews. 57. Elsevier BV: 101473. doi:10.1016/j.smrv.2021.101473. PMID 33853035. S2CID 233242139. Initial rodent studies showed that injections of dronabinol, a synthetic form of delta-9-tetrahydrocannabinol, in the nodose ganglia suppressed serotonin induced reflex apneas and increased upper airway dilating muscle activity during sleep. Limited studies in humans with moderate-to-severe OSA have demonstrated significant reduction in AHI with dronabinol use.

[fda-5] "Marinol (Dronabinol)" (PDF). US Food and Drug Administration. September 2004. Retrieved 14 January 2018.

[6] "Cannabis and Cannabinoids". National Cancer Institute. 2011-10-24. Retrieved 12 January 2014.

[7] Badowski ME (September 2017). "A review of oral cannabinoids and medical marijuana for the treatment of chemotherapy-induced nausea and vomiting: a focus on pharmacokinetic variability and pharmacodynamics". Cancer Chemotherapy and Pharmacology. 80 (3): 441–449. doi:10.1007/s00280-017-3387-5. PMC 5573753. PMID 28780725.

[8] "List of psychotropic substances under international control". International Narcotics Control Board. Retrieved 25 April 2018. This international non-proprietary name refers to only one of the stereochemical variants of delta-9-tetrahydrocannabinol, namely (−)-trans-delta-9-tetrahydrocannabinol

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Dronabinol

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