N-Arachidonylglycine-d8 is a deuterated labeled N-Arachidonylglycine[1]. N-Arachidonylglycine (NA-Gly), a carboxylic analog of the endocannabinoid anandamide (AEA), is a GPR18 agonist (EC50 = 44.5 nM). Unlike AEA, N-Arachidonylglycine has no activity at either CB1 or CB2 receptors. N-Arachidonylglycine inhibits GLYT2 (IC50 = 5.1 μM). N-Arachidonylglycine also is an effective activator of endometrial cell migration[2][3].
Arachidonoyl glycine-d8 (NAGly-d8) contains eight deuterium atoms at the 5, 6, 8, 9, 11, 12, 14, and 15 positions. It is intended for use as an internal standard for the quantification of NAGly by GC- or LC-mass spectrometry. NAGly has been isolated from cell cultures treated with arachidonoyl ethanolamide (AEA),1 from extracts of mammalian brain,2,3 and has also been synthesized as an analog of AEA for structure/activity testing.4 NAGly may be produced endogenously via oxidation of AEA, or by transacylation of arachidonoyl coenzyme A. NAGly is reported to have analgesic activities in whole animal experiments.1,2,3 Since it seems to be a very poor ligand for the CB1 receptor,4 these effects are probably mediated via other signalling pathways.
1.Burstein, S.H., Rossetti, R.G., Yagen, B., et al.Oxidative metabolism of anandamideProstaglandins & Other Lipid Mediators6129-41(2000)
2.Huang, S.M., Bisogno, T., Petros, T.J., et al.Identification and characterization of an endogenous anandamide-like compound: N-arachidonylglycine (NAGly)ICRS 2001 Symposium on the Cannabinoids78(2001)
3.Huang, S.M., Bisogno, T., Petros, T.J., et al.Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits painThe Journal of Biological Chemisty276(46)42639-42644(2001)
4.Sheskin, T., Hanus, L., Slager, J., et al.Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptorJournal of Medicinal Chemistry40659-667(1997)
