Dexanabinol
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ATC code |
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ECHA InfoCard | 100.201.022 |
Chemical and physical data | |
Formula | C25H38O3 |
Molar mass | 386.576 g·mol−1 |
3D model (JSmol) | |
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Dexanabinol (HU-211 or ETS2101[1]) is a synthetic cannabinoid derivative in development by e-Therapeutics plc. It is the "unnatural" enantiomer of the potent cannabinoid agonist HU-210.[2] Unlike other cannabinoid derivatives, HU-211 does not act as a cannabinoid receptor agonist, but instead as an NMDA antagonist.[3] It therefore does not produce cannabis-like effects, but is anticonvulsant and neuroprotective, and is widely used in scientific research as well as currently being studied for applications such as treating head injury, stroke, or cancer.[4][5][6] It was shown to be safe in clinical trials[7] and is currently undergoing Phase I trials for the treatment of brain cancer[8] and advanced solid tumors.[9]
Clinical trials
[edit]Dexanabinol has been studied in IV administration and oral dosing.[10] e-Therapeutics is evaluating the compound in clinical trials for brain and solid cancers.[11] Phase II studies are planned based on the results of the current trials.
A phase 1b study for hepatocellular carcinoma and pancreatic cancer was started in 2015.[12]
Legal status
[edit]HU-211 is not listed in the schedules set out by the United Nations' Single Convention on Narcotic Drugs from 1961 nor their Convention on Psychotropic Substances from 1971,[13] so the signatory countries to these international drug control treaties are not required by said treaties to control HU-211.
United States
[edit]HU-211 is not listed in the list of scheduled controlled substances in the USA.[14] It is therefore not scheduled at the federal level in the United States, but it is possible that HU-211 could legally be considered an analog of Delta-8-THC (one of the THC isomers which is in Schedule I under the designation of "Tetrahydrocannabinols"), and therefore sales or possession could potentially be prosecuted under the Federal Analogue Act.[15]
HU-211 is a Schedule I controlled substance in Alabama.[16]
HU-211 is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[17]
Effective January 1, 2016, HU-211 is a regulated drug in Vermont designated as a "Hallucinogenic Drug."[18]
See also
[edit]References
[edit]- ^ "e-therapeutics Clinical Development Pipeline". Archived from the original on 2013-01-26. Retrieved 2012-10-23.
- ^ Pop E (September 2000). "Nonpsychotropic synthetic cannabinoids". Current Pharmaceutical Design. 6 (13): 1347–60. doi:10.2174/1381612003399446. PMID 10903397.
- ^ Feigenbaum JJ, Bergmann F, Richmond SA, Mechoulam R, Nadler V, Kloog Y, Sokolovsky M (December 1989). "Nonpsychotropic cannabinoid acts as a functional N-methyl-D-aspartate receptor blocker". Proceedings of the National Academy of Sciences of the United States of America. 86 (23): 9584–7. Bibcode:1989PNAS...86.9584F. doi:10.1073/pnas.86.23.9584. PMC 298542. PMID 2556719.
- ^ Biegon A, Joseph AB (August 1995). "Development of HU-211 as a neuroprotectant for ischemic brain damage". Neurological Research. 17 (4): 275–80. doi:10.1080/01616412.1995.11740326. PMID 7477742.
- ^ Darlington CL (October 2003). "Dexanabinol: a novel cannabinoid with neuroprotective properties". IDrugs. 6 (10): 976–9. PMID 14534855.
- ^ Vink R, Nimmo AJ (January 2009). "Multifunctional drugs for head injury". Neurotherapeutics. 6 (1): 28–42. doi:10.1016/j.nurt.2008.10.036. PMC 5084254. PMID 19110197.
- ^ Maas AI, Murray G, Henney H, Kassem N, Legrand V, Mangelus M, et al. (January 2006). "Efficacy and safety of dexanabinol in severe traumatic brain injury: results of a phase III randomised, placebo-controlled, clinical trial". The Lancet. Neurology. 5 (1): 38–45. doi:10.1016/S1474-4422(05)70253-2. PMID 16361021. S2CID 28268833.
- ^ University of California, San Diego "Synthetic Cannabinoid May Be Used as Brain Cancer Treatment". (28 September 2012) Laboratory Equipment. Retrieved 28 September 2012.
- ^ "A Phase 1 Study of Dexanabinol in Patients With Advanced Solid Tumours". ClinicalTrials.gov. NIH. January 26, 2015.
- ^ "e-Therapeutics Reports Progress in ETS2101 Phase 1a and Oral Dosing Studies" (PDF). 18 December 2014. Archived from the original (PDF) on 5 February 2015.
- ^ "Clinical Development Pipeline". Archived from the original on February 5, 2015. Retrieved Feb 5, 2015.
- ^ "A Study of Dexanabinol in Combination With Chemotherapy in Patients With Advanced Tumours - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2015-09-18.
- ^ "UN International Drug Control Conventions". Archived from the original on 2014-03-17. Retrieved 2016-08-07.
- ^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
- ^ Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary
- ^ "Alabama Senate Bill 333 - Controlled substances, Schedule I, additional synthetic controlled substances and analogue substances included in, trafficking in controlled substance analogues, requisite weight increased, Secs. 13A-12-231, 20-2-23 am'd". March 2014. Retrieved 2 February 2017.
- ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
- ^ Vermont DOH - Regulated Drug Rule 2016 .PDF