536697-79-7 Usage
Description
O-1918 is a cannabidiol analog and a selective antagonist at the endothelial cannabidiol receptor, specifically targeting the GPR18 receptor. It possesses the ability to induce endothelium-dependent vasodilation, making it a potential candidate for various medical applications.
Uses
Used in Pharmaceutical Industry:
O-1918 is used as a pharmaceutical agent for its ability to selectively target the endothelial cannabidiol receptor (GPR18). This selective antagonism may have potential therapeutic applications in treating conditions related to the endothelial cannabidiol receptor's function.
Used in Cardiovascular Applications:
O-1918 is used as a vasodilator for its ability to induce endothelium-dependent vasodilation. This property may be beneficial in treating cardiovascular conditions where improved blood flow and reduced strain on the heart are desired.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 536697-79-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 5,3,6,6,9 and 7 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 536697-79:
(8*5)+(7*3)+(6*6)+(5*6)+(4*9)+(3*7)+(2*7)+(1*9)=207
207 % 10 = 7
So 536697-79-7 is a valid CAS Registry Number.
InChI:InChI=1/C19H26O2/c1-12(2)15-8-7-13(3)9-16(15)19-17(20-5)10-14(4)11-18(19)21-6/h9-11,15-16H,1,7-8H2,2-6H3/t15-,16+/m0/s1
536697-79-7Relevant articles and documents
Selective ligands and cellular effectors of a G protein-coupled endothelial cannabinoid receptor
Offertaler, Laszlo,Mo, Fong-Ming,Batkai, Sandor,Liu, Jie,Begg, Malcolm,Razdan, Raj K.,Martin, Billy R.,Bukoski, Richard D.,Kunos, George
, p. 699 - 705 (2003)
The cannabinoid analog abnormal cannabidiol [abn-cbd; (-)-4-(3-3,4-trans-p-menthadien-[1,8]-yl)-olivetol] does not bind to CB1 or CB2 receptors, yet it acts as a full agonist in relaxing rat isolated mesenteric artery segments. Vasorelaxation by abn-cbd is endothelium-dependent, pertussis toxin-sensitive, and is inhibited by the BKca channel inhibitor charybdotoxin, but not by the nitric-oxide synthase inhibitor Nω-nitro-L-arginine methyl ester or by the vanilloid VR1 receptor antagonist capsazepine. The cannabidiol analog O-1918 does not bind to CB1 or CB2 receptors and does not cause vasorelaxation at concentrations up to 30 μM, but it does cause concentration-dependent (1-30 μM) inhibition of the vasorelaxant effects of abn-cbd and anandamide. In anesthetized mice, O-1918 dose-dependently inhibits the hypotensive effect of abn-cbd but not the hypotensive effect of the CB1 receptor agonist (-)-11-Δ9-tetrahydro-cannabinol dimethylheptyl. In human umbilical vein endothelial cells, abn-cbd induces phosphorylation of p42/44 mitogen-activated protein kinase and protein kinase B/Akt, which is inhibited by O-1918, by pertussis toxin or by phosphatidylinositol 3 (PI3) kinase inhibitors. These findings indicate that abn-cbd is a selective agonist and that O-1918 is a selective, silent antagonist of an endothelial anandamide receptor , which is distinct from CB1 or CB2 receptors and is coupled through Gi/Go to the PI3 kinase/Akt signaling pathway.