1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol
- CAS No.
- 112924-45-5
- Chemical Name:
- 1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol
- Synonyms
- Dexanabinol;1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol;(6aS,10aS)-3-(1,1-dimethylheptyl)-6,6-dimethyl-9-methylol-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol;(6aS,10aS)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol;(6aS)-6aα,7,10,10aβ-Tetrahydro-6,6-dimethyl-1-hydroxy-3-(1,1-dimethylheptyl)-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;[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)-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)-TRANS-3-(1,1-DIMETHYLHEPTYL)-6A,7,10,10A-TETRAHYDRO-1-HYDROXY-6,6-DIMETHYL-6H-DIBENZO[B,D]PYRAN-9-METHANOL
- CBNumber:
- CB2151489
- Molecular Formula:
- C25H38O3
- Molecular Weight:
- 386.57
- MDL Number:
- MFCD01074786
- MOL File:
- 112924-45-5.mol
| Melting point | 141-142° |
|---|---|
| alpha | D +227° (CHCl3) |
| Boiling point | 470.1±45.0 °C(Predicted) |
| Density | 1.030±0.06 g/cm3(Predicted) |
| storage temp. | −20°C |
| solubility | DMSO: soluble |
| pka | 9.72±0.60(Predicted) |
| form | solid |
| FDA UNII | R6VT8U5372 |
| NCI Drug Dictionary | dexanabinol |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS08,GHS07 |
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|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H332-H319-H315-H312-H361-H302-H335 | |||||||||
| Precautionary statements | P261-P271-P304+P340-P312-P264-P270-P301+P312-P330-P501-P264-P280-P305+P351+P338-P337+P313P-P201-P202-P281-P308+P313-P405-P501-P264-P280-P302+P352-P321-P332+P313-P362-P280-P302+P352-P312-P322-P363-P501 | |||||||||
| WGK Germany | 3 | |||||||||
| NFPA 704 |
|
1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol Chemical Properties,Uses,Production
Uses
HU 211-d6 is labelled HU-211 (H673505) which is a novel TNF-α inhibitor and an effective neuroprotectant. It might be a useful agent for the treatment of stroke patients, by protecting neuronal lysosomes from nitric oxide (NO)-mediated toxicity.
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.