Dexanabinol

Dexanabinol
Clinical data
ATC code
  • none
Identifiers
  • (6aS,10aS)-9-(Hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.201.022
Chemical and physical data
FormulaC25H38O3
Molar mass386.576 g·mol−1
3D model (JSmol)
  • Oc2cc(cc1OC([C@H]3C/C=C(\C[C@@H]3c12)CO)(C)C)C(C)(C)CCCCCC
  • InChI=1S/C25H38O3/c1-6-7-8-9-12-24(2,3)18-14-21(27)23-19-13-17(16-26)10-11-20(19)25(4,5)28-22(23)15-18/h10,14-15,19-20,26-27H,6-9,11-13,16H2,1-5H3/t19-,20-/m0/s1 ☒N
  • Key:SSQJFGMEZBFMNV-PMACEKPBSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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

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]

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

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

References

  1. ^ "e-therapeutics Clinical Development Pipeline". Archived from the original on 2013-01-26. Retrieved 2012-10-23.
  2. ^ Pop E (September 2000). "Nonpsychotropic synthetic cannabinoids". Current Pharmaceutical Design. 6 (13): 1347–60. doi:10.2174/1381612003399446. PMID 10903397.
  3. ^ 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.
  4. ^ 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.
  5. ^ Darlington CL (October 2003). "Dexanabinol: a novel cannabinoid with neuroprotective properties". IDrugs. 6 (10): 976–9. PMID 14534855.
  6. ^ 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.
  7. ^ 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.
  8. ^ University of California, San Diego "Synthetic Cannabinoid May Be Used as Brain Cancer Treatment". (28 September 2012) Laboratory Equipment. Retrieved 28 September 2012.
  9. ^ "A Phase 1 Study of Dexanabinol in Patients With Advanced Solid Tumours". ClinicalTrials.gov. NIH. January 26, 2015.
  10. ^ "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.
  11. ^ "Clinical Development Pipeline". Archived from the original on February 5, 2015. Retrieved Feb 5, 2015.
  12. ^ "A Study of Dexanabinol in Combination With Chemotherapy in Patients With Advanced Tumours - Full Text View - ClinicalTrials.gov". clinicaltrials.gov. Retrieved 2015-09-18.
  13. ^ "UN International Drug Control Conventions". Archived from the original on 2014-03-17. Retrieved 2016-08-07.
  14. ^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  15. ^ Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary
  16. ^ "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.
  17. ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
  18. ^ Vermont DOH - Regulated Drug Rule 2016 .PDF
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