| Identification | Back Directory | [Name]
O-1918 | [CAS]
536697-79-7 | [Synonyms]
O-1918
1,3-DIMETHOXY-5-METHYL-2-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-BENZENE
Benzene, 1,3-dimethoxy-5-methyl-2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]- | [Molecular Formula]
C19H26O2 | [MDL Number]
MFCD08062137 | [MOL File]
536697-79-7.mol | [Molecular Weight]
286.41 |
| Chemical Properties | Back Directory | [Boiling point ]
383.9±42.0 °C(Predicted) | [density ]
0.981±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO > 10 mM | [form ]
Powder | [color ]
Colorless to light yellow |
| Hazard Information | Back Directory | [Uses]
O-1918 is a cannabidiol analog and a selective antagonist at the endothelial cannabidiol receptor. It is an inhibitor of GPR18. O-1918 can also induce endothelium-dependent vasodilation. | [Biological Activity]
Selective, silent antagonist of a putative endothelial anandamide receptor distinct from CB 1 or CB 2 receptors. Inhibits vasodilation and cell migration induced by abnormal-cannabidiol (abn-CBD; 4-[(1R,6R)-3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol). | [Enzyme inhibitor]
This endocannabinoid antagonist (FW = 286.42 g/mol; CAS 536697-79-7), systematically named 1,3-dimethoxy-5-methyl-2-[(1R,6R)-3-methyl-6-(1- methylethenyl)-2-cyclohexen-1-yl]benzene, is a cannabidinodiol analogue that selectively targets a putative G-coupled endothelial anandamide receptor that is distinct from CB1 or CB2 endocannabinoid receptors. O- 1918 does not bind to CB1 or CB2 receptors and does not cause vasorelaxation at concentrations up to 30 μM, but inhibits the vasorelaxant effects of abn-cbd and anandamide in a concentration-dependent manner (1- 30 μM). (See abn-cbd; Anandamide; Oleamide). While the atypical cannabinoids O-1602 and abn-cbd (or abnormal cannabidiol) stimulate GPR55-dependent GTPgS activity (EC50 ~ 2 nM), O-1918 antagonizes such effects. O-1918 is involved in the delayed hypotension induced by anandamide in anaesthetized rats. | [in vivo]
Decreases in HR, blood pressure, MBF and RBF by about 20 beats/min, 5-10 mmHg and 0.7 and 0.2 mL/min, respectively, are observed after injection of O1918 (3 μmol/kg). O1918 causes an inhibition of the anandamide-stimulated decreases in MBP, SBP and DBP by 55, 38 and 42% respectively. Similarly, this antagonist reduces the methanandamide-stimulated fall in SBP and DBP by 44 and 32%, respectively, and tends to diminish the decrease in MBP by 28%. O1918 also diminishes the fall in MBF and RBF induced by anandamide by 61 and 67% and that induced by methanandamide by 74 and 49% respectively. Cannabidiol does not affect basal cardiovascular parameters whereas O1918 decreases HR by about 15 beats/min and SBP, DBP and MBP by about 15 mmHg. In pithed rats anandamide (3 μmol/kg) causes only an increase in MBF and RBF. The anandamide-induced long-lasting fall in MBP, SBP and DBP is reduced by cannabidiol by 40-46% and by O-1918 by 55, 64 and 35, respectively[1]. | [storage]
Store at -20°C |
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