N-Arachidonoyl-L-Serine-d₈

N-Arachidonoyl-L-serine-d₈ (ARA-S-d₈) contains eight deuterium atoms at the 5, 6, 8, 9, 11, 12, 14, and 15 positions. It is intended for use as an internal standard for the quantification of ARA-S (Item No. 10005455) by GC- or LC-mass spectrometry. Arachidonoyl amides of both amino acids and neurotransmitters such as dopamine have been previously reported in the literature.¹ ARA-S is one such recently isolated endocannabinoid with an unusual activity profile. ARA-S does not bind to CB₁ and CB₂ receptors or vanilloid receptor 1. Like cannabidiol (Item No. 90080), ARA-S (5 mg/kg) antagonizes the hypotensive effects of a 10 mg/kg IV bolus of abnormal cannabidiol (Abn-CBD, CAY10429 Item No. 10004259) 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 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.

WARNING This product is not for human or veterinary use.

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).

Naoe, S., Tsugawa, H., Takahashi, M., et al. Characterization of lipid profiles after dietary intake of polyunsaturated fatty acids using integrated untargeted and targeted lipidomics. Metabolites 9(10), 241 (2019).