112924-45-5

Basic information

• Product Name: 1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol
• Synonyms: (6AR)-TRANS-3-(1,1-DIMETHYLHEPTYL)-6A,7,10,10A-TETRAHYDRO-1-HYDROXY-6,6-DIMETHYL-6H-DIBENZO[B,D]PYRAN-9-METHANOL;(6AR,10AR)-3-(1,1'-DIMETHYLHEPTYL)-6A,7,10,10A-TETRAHYDRO-1-HYDROXY-6,6-DIMETHYL-6H-DIBENZO[B,D]PYRAN-9-METHANOL;(6AR,10AR)-3(1,1-DIMETHYLHEPTYL)-6A,7,10,10A-TETRAHYDRO-1-HYDROXY-6,6-DIMETHYL-6H-DIBENZO[B,D]PYRAN-9-METHANOL;1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol;Dexanabinol;(6aS)-6aα,7,10,10aβ-Tetrahydro-6,6-dimethyl-1-hydroxy-3-(1,1-dimethylheptyl)-6H-dibenzo[b,d]pyran-9-methanol;[6aS,(+)]-6a,7,10,10aβ-Tetrahydro-1-hydroxy-6,6-dimethyl-3-(1,1-dimethylheptyl)-6H-dibenzo[b,d]pyran-9-methanol;(6aS,10aS)-3-(1,1-dimethylheptyl)-6,6-dimethyl-9-methylol-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
• CAS NO: 112924-45-5
• Molecular Formula: C₂₅H₃₈O₃
• Molecular Weight: 386.57
• Mol File: 112924-45-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 141-142°
• Boiling Point: 470.1 °C at 760 mmHg
• Flash Point: 238.1 °C
• Appearance: /solid
• Density: 1.03g/cm³
• Vapor Pressure: 1.22E-09mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: −20°C
• Solubility: DMSO: soluble
• PKA: 9.72±0.60(Predicted)
• CAS DataBase Reference: 1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol(112924-45-5)
• EPA Substance Registry System: 1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol(112924-45-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 112924-45-5(Hazardous Substances Data)

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

• 18309-32-5 Verbenone 
• 113473-31-7 [(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl 2,2-dimethylpropanoate 
• 6712-78-3 myrtenol 
• 56469-10-4 5-(1',1'-dimethyl-n-heptyl)-1,3-dihydroxybenzene 
• 113449-78-8 dexanabinol pivalate 
• 76163-95-6 (1R,5S)-2-[(2,2-dimethylpropoyloxy)methyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene 
• 19894-97-4 (1R)-Myrtenol 
• 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 
• 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 
• 76163-97-8 2,2-Dimethyl-propionic acid (1R,5R)-4-hydroxy-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethyl ester 
• 926645-58-1 [(1S,5R)-4-hydroxy-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methyl 2,2-dimethylpropanoate 
• 113473-32-8 [(1S,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]hept-2-en-2-yl]methyl 2,2-dimethylpropanoate 

Downstream Products

• 140835-14-9 [3H]-HU 243 

Relevant articles and documents

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.

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.