2-Arachidonoyl Glycerol-d₅

2-Arachidonoyl glycerol-d₅ (2-AG-d₅) is intended for use as an internal standard for the quantification of 2-AG (Item No. 62160) by GC- or LC-MS. 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

WARNING This product is not for human or veterinary use.

1. Stella, N., Schweitzer, P., and Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388(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 compounds. The Journal of Biological Chemisty 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 mechanisms. FEBS Lett. 429(2), 152-156 (1998).

4. Dinh, T.P., Carpenter, D., Leslie, F.M., et al. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc. Natl. Acad. Sci. USA 99(16), 10819-10824 (2002).

Tufail, Y.Z., Guijas, C., Kummer, D.A., et al. Suppression of pain transmission and behavior by inhibition of peripheral diacylglycerol metabolism. Cell Chem. Bio. 33(1), 74-90.e19 (2025).

Shin, M., Buckner, A., Prince, J., et al. Diacylglycerol lipase-b is required for TNF-a response but not CD8⁺ T cell priming capacity of dendritic cells. Cell Chem. Bio. 26, 1-6 (2019).

Butler, C.R., Beck, E.M., Harris, A.R., et al. Azetidine and piperidine carbamates as efficient, covalent inhibitors of monoacylglycerol lipase. J. Med. Chem. 60(23), 9860-9873 (2017).