Dronabinol
From Wikipedia, the free encyclopedia
- Marinol is also a commercial name for an ethanol-based liquid fuel sold for use in portable stoves, sold under this name at least in Finland. It can also refer to a brand-name fish oil concentrate supplement.
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Dronabinol
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| Systematic (IUPAC) name | |
| (−)-(6aR,10aR)-6,6,9-trimethyl-3-pentyl-
6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol |
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| Identifiers | |
| CAS number | |
| ATC code | A04 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C21H30O2 |
| Mol. mass | 314.462 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 5-20% (oral) |
| Protein binding | 97-99% |
| Metabolism | Hepatic |
| Half life | 25-36 hours |
| Excretion | Renal |
| Therapeutic considerations | |
| Pregnancy cat. |
C |
| Legal status | |
| Routes | Oral |
Dronabinol, sold as Marinol® (a registered trademark of Solvay Pharmaceuticals, Inc.), is the International Nonproprietary Name (INN) of Δ9-tetrahydrocannabinol (THC). THC is a naturally occurring component in cannabis. While THC is the main psychoactive substance in cannabis, dronabinol preparations do not contain the other significant chemical constituents present in cannabis.
Dronabinol is a FDA-approved cannabinoid and is prescribed as an appetite stimulant, primarily for AIDS, chemotherapy and gastric bypass patients. Dronabinol was also FDA approved as an anti-emetic, in order to better address the nausea experienced after chemotherapy treatments. Compare Sativex, a mouth spray for neuropathic pain of multiple sclerosis sufferers approved for use in Canada and in the US as of 2006. While dronabinol can serve as an anti-emetic and appetite booster, its immunomodulative effect should be taken into account in the treatment of any compromised immune condition[1].
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[edit] Comparisons to medicinal cannabis
Dronabinol is known to produce side-effects similar to cannabis intoxication. Some have posited that dronabinol lacks beneficial properties of cannabis, which contains more than 60 cannabinoids, including cannabidiol (CBD), thought to be the major anti-convulsant that helps multiple sclerosis patients, and cannabichromene (CBC), an anti-inflammatory which may contribute to the pain-killing effect of cannabis. Others have countered that the effects of all of cannabis's cannabinoids have not been completely studied and are not fully understood to be beneficial.
It takes over one hour for Marinol to reach full systemic effect, compared to minutes for smoked or vaporized cannabis. Some patients accustomed to inhaling just enough cannabis smoke to manage symptoms have complained of too-intense intoxication via Marinol's predetermined dosages. This powerful psychoactive effect, however, has led to recreational use of Marinol.[1] Many have said that Marinol produces a more acute psychedelic effect than cannabis and it has been speculated that this disparity can be explained by the moderating effect of the many non-THC cannibinoids present in cannabis. Mark Kleiman, director of the Drug Policy Analysis Program at UCLA's School of Public Affairs had this to say about Marinol-- "It wasn't any fun and made the user feel bad," Kleiman says, "so it could be approved without any fear that it would penetrate the recreational market, and then used as a club with which to beat back the advocates of whole cannabis as a medicine."[2] United States federal law currently registers Dronabinol as a Schedule III controlled substance, but all other Cannabis remains Schedule I, except Nabilone. Taking a Marinol pill to manage nausea can be ineffective because nausea can cause the pill to be ejected before it is absorbed by the body.
[edit] Regulatory history
Since at least 1986, the trend has been for THC in general, and especially the Marinol preparation, to be downgraded to less and less stringently-controlled schedules of controlled substances, in the U.S. and internationally.
On July 13, 1986, the Drug Enforcement Administration (DEA) issued a Final Rule and Statement of Policy authorizing the "Rescheduling of Synthetic Dronabinol in Sesame Oil and Encapsulated in Soft Gelatin Capsules From Schedule I to Schedule II"(DEA 51 FR 17476-78). This permitted medical use of Marinol, albeit with the severe restrictions associated with Schedule II status. For instance, refills of Marinol prescriptions were not permitted. At its 1045th meeting, on April 29, 1991, the Commission on Narcotic Drugs, in accordance with article 2, paragraphs 5 and 6, of the Convention on Psychotropic Substances, decided that Δ9-tetrahydrocannabinol (also referred to as Δ9-THC) and its stereochemical variants should be transferred from Schedule I to Schedule II of that Convention. This released Marinol from the restrictions imposed by Article 7 of the Convention[2].
An abstract published in the April-June 1998 issue of the Journal of Psychoactive Drugs found that "Healthcare professionals have detected no indication of scrip-chasing or doctor-shopping among the patients for whom they have prescribed dronabinol"[3]. The authors suggested that Marinol had a low potential for abuse.
In 1999, Marinol was rescheduled from Schedule II to III of the Controlled Substances Act, reflecting a finding that THC had a potential for abuse less than that of cocaine, and heroin. This rescheduling comprised part of the argument for a 2002 petition for cannabis rescheduling in the United States, in which petitioner Jon Gettman noted, "Cannabis is a natural source of dronabinol (THC), the ingredient of Marinol, a Schedule III drug. There are no grounds to schedule cannabis in a more restrictive schedule than Marinol"[4].
At its 33rd meeting, the World Health Organization Expert Committee on Drug Dependence recommended transferring tetrahydrocannabinol to Schedule IV of the Convention, citing its medical uses and low abuse potential. This would put THC in the Convention's least stringently-controlled Schedule.
[edit] External links
- http://www.marinol.com/
- Is Marinol better medicine than marijuana? Debate on Marinol in a pro-con format
[edit] References
- ^ Cabral GA, Staab A (2005). "Effects on the immune system". Handb Exp Pharmacol (168): 385–423. PMID 16596782.
- ^ Greenberg, Gary. "Respectable Reefer", Mother Jones, 2005-11-01. Retrieved on 2007-04-03.
- Calhoun, S. R., Galloway, G. P., and Smith, D. E. (1998). Abuse potential of dronabinol (Marinol). Journal of Psychoactive Drugs, 30, 187-196.
- DEA Moves Marinol To Schedule Three, But Leaves Marijuana in Schedule One. The Magic of Sesame Oil, Richard Cowan, MarijuanaNews.Com.
- Petition to Reschedule Cannabis (Marijuana) per 21 CFR §1308.44(b), Filed October 9, 2002 with the DEA by the Coalition for Rescheduling Cannabis.
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