Dronabinol

Effects

Overview

Synthetically created Δ9-THC, the main psychoactive ingredient in cannabis. TS

Dronabinol (INN (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 and antiemetic 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.[1][2][3] WP

Dronabinol is the principal psychoactive constituent enantiomer form, (−)-trans-Δ⁹-tetrahydrocannabinol, found in Cannabis sativa L. plants, but can also be synthesized in the laboratory. Dronabinol does not include any other tetrahydrocannabinol (THC) isomers or any cannabidiol (CBD).[4] WP

History

History

While dronabinol was initially approved by the United States Food and Drug Administration (FDA) on May 31, 1985, it was not until May 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.[5][6] WP

On April 29, 1991, the Commission on Narcotic Drugs, in accordance with article 2, paragraphs 5 and 6, of the Convention on Psychotropic Substances of 1971, 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 Δ⁹-THC from many of the restrictions imposed by the convention, facilitating its marketing as medication.[7] WP

An article published in the April–June 1998 issue of the Journal of Psychoactive Drugs found that "Healthcare professionals have detected no indication of script-chasing or doctor-shopping among the patients for whom they have prescribed dronabinol". The authors state that Marinol has a low potential for abuse.[8] WP⚠ Wikipedia itself has flagged this text: better source needed.

In 1999, in the United States, Marinol was rescheduled from Schedule II to Schedule III of the Controlled Substances Act, reflecting a finding that dronabinol had a potential for abuse less than that of cocaine and heroin. This rescheduling constituted part of the argument for a 2002 petition for removal of cannabis from Schedule I of the Controlled Substances Act, 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".[5][9] WP⚠ Wikipedia itself has flagged this text: better source needed.

In 2003, the World Health Organization Expert Committee on Drug Dependence recommended transferring THC to Schedule IV of the convention, citing its medical uses and low abuse potential. In 2019, the Committee recommended transferring Δ⁹-THC to Schedule I of the Single Convention on Narcotic Drugs of 1961, but its recommendations were rejected by the United Nations Commission on Narcotic Drugs.[10][11] WP

Legal status

Brand names

Dronabinol is marketed as Marinol and Syndros, a registered trademark of Solvay Pharmaceuticals. Dronabinol is also marketed, sold, and distributed by PAR Pharmaceutical Companies under the terms of a license and distribution agreement with SVC pharma LP, an affiliate of Rhodes Technologies for Marinol and Insys Pharmaceuticals for Syndros. Dronabinol is available as a prescription drug (under Marinol and Syndros) in several countries including the United States, Germany, South Africa and Australia. In Canada, Tetra Bio-Pharma filed a New Drug Submission (NDS) with Health Canada for its Dronabinol Soft Gel capsules to be marketed as Reduvo. Tetra has two other dronabinol drugs with new routes of administration which limit first-pass metabolism; an inhaled THC-based dronabinol drug and their mucoadhesive-delivery dronabinol drug Adversa, which are both in the accelerated 505(b)(2) New Drug Application (NDA) pathway for the U.S. and Canadian markets.[12–16] WP⚠ Wikipedia itself has flagged this text: citation needed.

In the United States, Marinol is a Schedule III drug, available by prescription, considered to be non-narcotic and to have a low risk of physical or mental dependence. Efforts to get cannabis rescheduled as analogous to Marinol have not succeeded thus far, though a 2002 petition has been accepted by the DEA. As a result of the rescheduling of Marinol from Schedule II to Schedule III, refills are now permitted for this substance. Marinol's U.S. Food and Drug Administration (FDA) approval for medical use has raised much controversy as to why cannabis is still illegal at the federal level.[17][18] WP

Pharmacology

Chemistry

Formula

C21H30O2 PC

CAS number

1972-08-3 PC

Molar mass (g/mol)

314.5 PC

IUPAC name (computed by PubChem)

(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol PC

SMILES

CCCCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O PC

InChIKey

CYQFCXCEBYINGO-IAGOWNOFSA-N PC

PubChem CID

16078

Pop culture

No references added yet.

References

1. Journal / agency Marinol (Dronabinol). September 2004
2. Other Cannabis and Cannabinoids. 2011-10-24
3. Journal / agency Badowski ME. 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. September 2017. doi:10.1007/s00280-017-3387-5 · PMID 28780725 · PMC5573753
4. Other List of psychotropic substances under international control
5. Other 1999 - Rescheduling of the Food and Drug Administration Approved Product Containing Synthetic Dronabinol [(-)-D9-(trans)-Tetrahydrocannabinol] in Sesame Oil and Encapsulated in Soft Gelatin Capsules From Schedule II to Schedule III. 1999-07-02
6. Other 51 Fed. Reg. 17476 (1986), Tuesday, May 13, 1986, pages 17476-17478
7. Other Riboulet-Zemouli K, Krawitz MA, Ghehiouèche F. The Crimson Digest (Vol. 1), Briefing on the international scientific assessment of Cannabis: Processes, stakeholders and history. 2018
8. Journal / agency Calhoun SR, Galloway GP, Smith DE. Abuse potential of dronabinol (Marinol). Journal of Psychoactive Drugs. 1998. doi:10.1080/02791072.1998.10399689 · PMID 9692381
9. Harm reduction site Petition to Reschedule Cannabis (Marijuana). 9 October 2002
10. Journal / agency WHO Expert Committee on Drug Dependence
11. Journal / agency Riboulet-Zemouli K, Krawitz MA, Ghehiouèche F. History, Science, and Politics of International Cannabis Scheduling, 2015–2021. FAAAT editions. 2021
12. Other EMCDDA, ELDD Comparative Study, May 2002
13. Other Marinol – the Legal Medical Use for the Marijuana Plant
14. Other Marijuana and Medicine: Cesamet, Marinol, Sativex
15. Other Tetra Bio-Pharma Files New Drug Submission for REDUVO™ in Canada. 30 December 2020
16. Other Tetra Bio-Pharma Hits Another Milestone Before Year End: Inhaled Dronabinol & MucoAdhesive Dronabinol 'Adversa'. 16 December 2020
17. Other Downs D. War on marijuana unconstitutional, doctors testify in federal court Monday. 21 October 2014
18. Other Eustice C. Medicinal Marijuana: A Continuing Controversy. 12 August 1997

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), TripSit factsheets, PubChem (public domain). Each value links to the exact revision it came from.