Arachidonoyl Serinol

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Background

Arachidonoyl Serinol is an amide bond-containing analogue of 2-arachidonoylglycerol, exhibited only weak CB1 receptor agonistic activity. 2-Arachidonoyl glycerol (2-AG), a product of increased inositol phospholipid metabolism, is the natural endocannabinoid ligand for the CB1 receptor [1][2][3]. Cannabinoid receptor (CB1) was first identified in rat brain in 1988. N-arachidonoylethanolamine (anandamide) binds to the cannabinoid receptor and exhibits various cannabimimetic activities. Anandamide inhibits calcium currents in N18 neuroblastoma cells, inhibits forskolin-stimulated adenylase cyclase activity, electrically evokes twitch response of the mouse vas deferens, and causes analgesia, hypothermia, hypoactivity, and catalepsy [3]. Anandamide acts as a weak agonist and 2-arachidonoylglycerol may be an endogenous cannabinoid receptor agonist in nervous tissues [1]. Replacement of the sn-2 oxygen in the glycerol moiety of 2-AG with a nitrogen atom produces Arachidonoyl Serinol. In NG108-15 cells, Arachidonoyl Serinol induced a weak elevation of [Ca2+]I [1][2].

[1]. Sugiura T, Kodaka T, Kondo S, et al. 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma x glioma hybrid NG108-15 cells. Biochem Biophys Res Commun. 1996 Dec 4;229(1):58-64.
[2]. Sugiura T1, Kodaka T, Kondo S, et al. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J Biochem. 1997 Oct;122(4):890-5.
[3]. Khanolkar AD, Abadji V, Lin S, et al. Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J Med Chem. 1996 Oct 25;39(22):4515-9.