Dexanabinol

Title: Dexanabinol
CAS Registry Number: 112924-45-5
CAS Name: (6aS,10aS)-3-(1,1-Dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9-methanol
Additional Names: (+)-(3S,4S)-7-hydroxy-D6-tetrahydrocannabinol-1,1-dimethylheptyl; (+)-11-OH-D8-THC-DMH
Manufacturers' Codes: HU-211
Molecular Formula: C25H38O3
Molecular Weight: 386.57
Percent Composition: C 77.67%, H 9.91%, O 12.42%
Literature References: NMDA antagonist. Nonpsychotropic derivative of tetrahydrocannabinol, q.v. Prepn: R. Mechoulam et al., DE 3735990; eidem, US 4876276 (1988, 1989 both to Yissum Res. Dev. Co.); R. Mechoulam et al., Tetrahedron: Asymmetry 1, 315 (1990). Cannabinoid receptor binding study: A. C. Howlett et al., Neuropharmacology 29, 161 (1990). Inhibition of nuclear factor-kB (NF-kB): E. Jüttler et al., Neuropharmacology 47, 580 (2004). Pharmacology: N. Eshhar et al., Eur. J. Pharmacol. 283, 19 (1995). Clinical pharmacokinetics: M. E. Brewster et al., Int. J. Clin. Pharmacol. Ther. 35, 361 (1995). Clinical evaluation in severe head injury: N. Knoller et al., Crit. Care Med. 30, 548 (2002).
Properties: Crystals from pentane, mp 141-142°. [a]D +227° (CHCl3).
Melting point: mp 141-142°
Optical Rotation: [a]D +227° (CHCl3)
Therap-Cat: Neuroprotective.
Keywords: Neuroprotective; NMDA Receptor Antagonist.
Dexetimide Dexmedetomidine Dextran Dextran Sulfate Sodium Dextranase

Dexanabinol
HU-211 structure.png
Systematic (IUPAC) name
(6aS,10aS)-9-(Hydroxymethyl)- 6,6-dimethyl- 3-(2-methyloctan-2-yl)- 6a,7,10,10a-tetrahydrobenzo [c]chromen-1-ol
Clinical data
Legal status  ?
Identifiers
CAS number 112924-45-5 YesY
ATC code None
PubChem CID 107778
ChemSpider 96934 N
UNII R6VT8U5372 YesY
Chemical data
Formula C25H38O3 
Mol. mass 386.567 g/mol
 N (what is this?)  (verify)

Dexanabinol (HU-211 or ETS2101[1]) is a synthetic cannabinoid derivative that 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 has NMDA antagonist effects.[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 practical applications such as treatment of head injury or 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]