Dronabinol
| Clinical data | |
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| Trade names | Marinol, Syndros |
| Other names | (−)-trans-Δ9-tetrahydrocannabinol |
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| Dependence liability | Physical: Low Psychological: Low–moderate |
| Addiction liability | Relatively low |
| Routes of administration | By mouth |
| Drug class | Cannabinoid |
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| Pharmacokinetic data | |
| Bioavailability | PO: 6–20% |
| Onset of action | PO: 0.5–1 hour |
| Elimination half-life | 25–36 hours |
| Duration of action | PO: 4–6 hours |
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| Chemical and physical data | |
| Formula | C21H30O2 |
| Molar mass | 314.469 g·mol−1 |
| 3D model (JSmol) | |
| Specific rotation | −152° (ethanol) |
| Boiling point | 155–157 °C (311–315 °F) 0.05mmHg,[1] 157–160°C @ 0.05mmHg[2] |
| Solubility in water | 0.0028 mg/mL (23 °C)[3] |
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| Cannabis |
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Dronabinol (INN), 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 US 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 (CBD).
- ^ 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