10007517  N-Arachidonyl Maleimide

NAM

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2-Arachidonoyl glycerol (2-AG) is an endogenous agonist of the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors.1,2,3 2-AG is present at relatively high levels in the central nervous system and is the most abundant molecular species of monoacylglycerol found in rat brain.1,4 Monoacylglycerol lipase (MGL) hydrolyzes 2-AG to arachidonic acid and glycerol, thereby terminating its biological actions.5 N-Arachidonyl maleimide (NAM) is a potent, irreversible inhibitor of MGL or MGL-like activity in rat cerebellar membranes, exhibiting an IC50 value of 140 nM.6 Inhibition of MGL by the sulfhydryl-reactive maleimide group of NAM suggests a critical cysteine residue is present in the substrate-binding site of the enzyme.
1  Stella, N., Schweitzer, P., Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (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. J Biol Chem 274 2794-2801 (1999).
3  Ben-Shabat, S., Fride, E., Sheskin, T., et al. An entourage effect: Inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity. Eur J Pharmacol 353 23-31 (1998).
4  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 429 152-156 (1998).
5  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).
6  Saario, S.M., Salo, O.M.H., Nevalainen, T., et al. Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes. Chemistry & Biology 12 649-656 (2005).


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Pricing updated 2010-03-19.
Prices are subject to change without notice.

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