N-Arachidonoyl-L-Serine

Arachidonoyl amides of both amino acids and neurotransmitters such as dopamine have been previously reported in the literature.¹ N-Arachidonoyl-L-serine (ARA-S) is one such recently isolated endocannabinoid with an unusual activity profile. ARA-S does not bind to central cannabinoid (CB₁) and peripheral cannabinoid (CB₂) receptors or vanilloid receptor 1 (VR1). Like cannabidiol, ARA-S (5 mg/kg) antagonizes the hypotensive effects of a 10 mg/kg IV bolus of abnormal cannabidiol (Abn-CBD) in an anesthetized rat blood pressure model.² However, similar to Abn-CBD, ARA-S relaxes isolated rat mesenteric arteries and abdominal aorta as well as increases phosphorylation of Akt and mitogen-activated protein kinase (MAPK) in HUVEC.³ The precise mechanisms of action by ARA-S and Abn-DBD in various vascular preparations appears to be different and requires further investigation.

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1. Bisogno, T., Melck, D., Bobrov, M.Y., et al. N-acyl-dopamines: Novel synthetic CB₁ cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo. Biochem. J. 351(Pt 3), 817-824 (2001).

2. Milman, G., Maor, Y., Horowitz, M., et al. Arachidonoyl-serine, an endocannabinoid-like bioactive constituent of rat brain. 14th Annual Symposium on the Cannabinoids 133 (2004).

3. Milman, G., Maor, Y., Abu-Lafi, S., et al. N-arachidonoyl L-serine, an endocannabinoid-like brain constituent with vasodilatory properties. Proc. Natl. Acad. Sci. USA 103(7), 2428-2433 (2006).