1-Arachidonoyl-d5-rac-glycerol

1-Arachidonyl-d5-rac-glycerol (1-AG-d5) is intended for use as an internal standard for the quantification of 1-AG (Item No. 62150) by GC- or LC-MS. The glyceryl esters of arachidonic acid have been proposed as endogenous cannabinoid ligands.1 2-AG is 10 to 100 times more potent than 1-AG in ligand binding affinity and agonist activity at the CB1 receptor,2 and is thus considered to be the natural ligand. However, 2-AG is chemically unstable and undergoes rapid isomerization to 1-AG (synonymous with 1(3)-AG) both in vitro and in vivo. 1-AG is a frequent contaminant in synthetic 2-AG preparations, and can markedly reduce their cannabinergic potency. 1-AG is a weak CB1 receptor agonist and may have other pharmacologic properties.WARNING This product is not for human or veterinary use.

[1] TAKAYUKI SUGIURA . 2-Arachidonoylglycerol, a Putative Endogenous Cannabinoid Receptor Ligand, Induces Rapid, Transient Elevation of Intracellular Free Ca2+in Neuroblastoma × Glioma Hybrid NG108-15 Cells[J]. Biochemical and biophysical research communications, 1996, 229 1: Pages 58-64. DOI: 10.1006/bbrc.1996.1757
[2] T SUGIURA. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor Structural requirements for triggering a Ca2+ transient in NG108-15 cells.[J]. Journal of biochemistry, 1997, 122 4: 890-895. DOI: 10.1093/oxfordjournals.jbchem.a021838
[3] ANNE-SOPHIE ARCHAMBAULT. Human and Mouse Eosinophils Differ in Their Ability to Biosynthesize Eicosanoids, Docosanoids, the Endocannabinoid 2-Arachidonoyl-glycerol and Its Congeners.[J]. Cells, 2022. DOI: 10.3390/cells11010141