2944. Dexanabinol
Nomenclature
CAS number: 112924-45-5
(6aS,10aS)-3-(1,1-Dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9-methanol; (+)-(3S,4S)-7-hydroxy-Δ6-tetrahydrocannabinol-1,1-dimethylheptyl; (+)-11-OH-Δ8-THC-DMH; HU-211. C25H38O3; mol wt 386.57.
C 77.67%, H 9.91%, O 12.42%.
Description and 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-κB (NF-κB): 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°. [α]D +227° (CHCl3).Therapeutic Category
Neuroprotective.
Keywords
Neuroprotective; NMDA Receptor Antagonist