Dexanabinol

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]

Dexanabinol

Clinical data
ATC code	none
Identifiers
IUPAC name (6aS,10aS)-9-(Hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number	112924-45-5 Y
PubChem CID	107778
DrugBank	DB06444 Y
ChemSpider	96934 N
UNII	R6VT8U5372
ChEMBL	ChEMBL334533
CompTox Dashboard (EPA)	DTXSID40150235
ECHA InfoCard	100.201.022
Chemical and physical data
Formula	C25H38O3
Molar mass	386.576 g·mol−1
3D model (JSmol)	Interactive image
SMILES Oc2cc(cc1OC([C@H]3C/C=C(\C[C@@H]3c12)CO)(C)C)C(C)(C)CCCCCC
InChI 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
NY (what is this?)  (verify)

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]

Legal status

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

• Etonitazene
• Norbinaltorphimine