2-Arachidonoyl glycerol-d5 (2-AG-d5) contains five deuterium atoms at the 1, 1, 2, 3, and 3 positions of the glycerol moiety. It is intended for use as an internal standard for the quantification of 2-AG by GC- or LC-mass spectrometry. 2-Arachidonoyl glycerol (2-AG) is an endogenous agonist of the CB1 receptor.1,2 Unlike anandamide, 2-AG is present at relatively high levels in the central nervous system; it is the most abundant molecular species of monoacylglycerol found in rat brain.1,3 Formation of 2-AG is calcium-dependent and is mediated by the activities of PLC and DAG lipase.1 2-AG acts as a full agonist at the CB1 receptor. At a concentration of 0.3 nM, 2-AG induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells through a CB1 receptor-dependent mechanism.2 2-AG is metabolized in vitro by MAG lipase and fatty acid amide hydrolase, with MAG lipase likely being the principle metabolizing enzyme in vivo.4
1.Stella, N., Schweitzer, P., and Piomelli, D.A second endogenous cannabinoid that modulates long-term potentiationNature388(6644)773-778(1997)
2.Sugiura, T., Kodaka, T., Nakane, S., et al.Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compoundsJ. Biol. Chem.274(5)2794-2801(1999)
3.Kondo, S., Kondo, H., Nakane, S., et al.2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanismsFEBS Letters429(2)152-156(1998)
4.Dinh, T.P., Carpenter, D., Leslie, F.M., et al.Brain monoglyceride lipase participating in endocannabinoid inactivationProceedings of the National Academy of Sciences of the United States of America99(16)10819-10824(2002)
