112924-45-5

Usage

Biological Activity

NMDA antagonist (IC 50 = 11 μ M for inhibition of [ 3 H]MK-801 binding to rat forebrain membranes). Protects against NMDA- and quisqualate-induced neurotoxicity (EC 50 = 3.8 μ M) and enhances dopamine D 1 receptor activity. Inhibits NF- κ B, reducing TNF- α , IL-6 and nitric oxide production, and acts as a free radical scavenger. Exhibits beneficial effects in experimental models of multiple sclerosis, bacterial meningitis, septic shock, epilepsy, and traumatic and ischemic brain injury. Brain penetrant.

references

[1]. eshhar n, striem s, biegon a. hu-211, a non-psychotropic cannabinoid, rescues cortical neurones from excitatory amino acid toxicity in culture. neuroreport, 1993, 5(3): 237-240.[2]. bar-joseph a, berkovitch y, adamchik j, et al. neuroprotective activity of hu-211, a novel nmda antagonist, in global ischemia in gerbils. mol chem neuropathol, 1994, 23(2-3): 125-135.[3]. shohami e, novikov m, bass r. long-term effect of hu-211, a novel non-competitive nmda antagonist, on motor and memory functions after closed head injury in the rat. brain res, 1995, 674(1): 55-62.[4]. gallily r, yamin a, waksmann y, et al. protection against septic shock and suppression of tumor necrosis factor alpha and nitric oxide production by dexanabinol (hu-211), a nonpsychotropic cannabinoid. j pharmacol exp ther, 1997, 283(2): 918-924.

InChI:InChI=1/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

Upstream product

• 113418-02-3 2,2-Dimethyl-propionic acid (6aR,10aR)-3-(1,1-dimethyl-heptyl)-1-hydroxy-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-9-ylmethyl ester 
• 19894-97-4 (1R)-Myrtenol 
• 113449-78-8 dexanabinol pivalate 
• 6712-78-3 myrtenol 
• 56469-10-4 5-(1',1'-dimethyl-n-heptyl)-1,3-dihydroxybenzene 
• 95925-03-4 10-hydroxyverbenone 
• 113473-32-8 [(1S,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]hept-2-en-2-yl]methyl 2,2-dimethylpropanoate 
• 926645-58-1 [(1S,5R)-4-hydroxy-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl 2,2-dimethylpropanoate 
• 18309-32-5 Verbenone 
• 113473-31-7 [(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl 2,2-dimethylpropanoate 
• 76163-95-6 (1R,5S)-2-[(2,2-dimethylpropoyloxy)methyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene 
• 76163-96-7 4-oxo-myrtenyl pivalate 
• 76163-97-8 4-hydroxy-myrtenyl pivalate 
• 76163-96-7 2,2-Dimethyl-propionic acid (1R,5R)-6,6-dimethyl-4-oxo-bicyclo[3.1.1]hept-2-en-2-ylmethyl ester 

Downstream Products

• 140835-14-9 [3H]-HU 243 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF 3-SUBSTITUTED CANNABINOID COMPOUNDS

There is described a method of preparing a compound of formula I, and optical isomers thereof: in which R1 is hydrogen or a protecting group; said method comprising oxidising verbenone and optical isomers thereof.

High enantiomeric purity dexanabinol for pharmaceutical compositions

The present invention relates to a synthetic cannabinoid, dexanabinol, of enantiomeric purity in excess of 99.90%, or to a pharmaceutically acceptable salt, ester or solvate of said compound. The present invention also relates to pharmaceutical grade compositions comprising said compound of high enantiomeric purity, and uses thereof for prevention and treatment of neurological disorders, chronic degenerative diseases, CNS poisoning, cognitive impairment, inflammatory diseases or disorders, autoimmune diseases or disorders, pain, emesis, glaucoma and wasting syndromes.

Dexanabinol derivatives and their use as neuroprotective pharmaceutical compositions

PCT No. PCT/US95/01470 Sec. 371 Date Sep. 28, 1998 Sec. 102(e) Date Sep. 28, 1998 PCT Filed Feb. 6, 1995 PCT Pub. No. WO95/20958 PCT Pub. Date Aug. 10, 1995The present invention relates to pharmaceutical compositions for preventing or alleviating neurotoxicity. Said pharmaceutical compositions comprise as their active ingredient the stereospecific (+) enantiomers, having (3S,4S) configuration, of DELTA 6-tetrahydrocannabinol (THC) type compounds of general formula (I), as defined hereinbelow.

SYNTHESIS OF THE INDIVIDUAL, PHARMACOLOGICALLY DISTINCT, ENANTIOMERS OF A TETRAHYDROCANNABINOL DERIVATIVE

The individual enantiomers of the 1,1-dimethylheptyl homolog of 7-hydroxy-Δ6-tetrahydrocannabinol, (1) and (2a), which exhibit distinct pharmacological profiles, have been obtained with very high e.e. by synthesis from the antipodes of myrtenol.