Arachidonoyl amide

Anandamide (AEA) is an endogenous cannabinoid that binds to both central cannabinoid (CB₁) and peripheral cannabinoid (CB₂) receptors. The biological actions of AEA are terminated by cellular uptake and hydrolysis of the amide bond by the enzyme fatty acid amide hydrolase (FAAH). Anandamide (AEA) is an endogenous cannabinoid that binds to both central cannabinoid (CB₁) and peripheral cannabinoid (CB₂) receptors. The biological actions of AEA are terminated by cellular uptake and hydrolysis of the amide bond by the enzyme fatty acid amide hydrolase (FAAH). Arachidonoyl amide is an analog of anandamide (AEA) that lacks the hydroxyethyl moiety. It is hydrolyzed by FAAH more effectively than AEA but exhibits significantly weaker binding to the human CB₁ receptor with a K_i of 9.6 µM.^1,2 Arachidonoyl amide and AEA exhibit similar binding and translocation into cells via the AEA transporter. It inhibits [³H]-AEA uptake into human astrocytoma cells with an IC₅₀ of 9 µM.³ Arachidonoyl amide also inhibits rat glial gap junction cell-cell communication by 90% at a concentration of 20 µM.⁴

WARNING This product is not for human or veterinary use.

1. Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc. Natl. Acad. Sci. USA 90(16), 7656-7660 (1993).

2. Lang, W., Qin, C., Lin, S., et al. Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase. J. Med. Chem. 42(5), 896-902 (1999).

3. Piomelli, D., Beltramo, M., Glasnapp, S., et al. Structural determinants for recognition and translocation by the anandamide transporter. Proc. Natl. Acad. Sci. USA 96(10), 5802-5807 (1999).

4. Boger, D.L., Sato, H., Lerner, A.E., et al. Arachidonic acid amide inhibitors of gap junction cell-cell communication. Bioorg. Med. Chem. Lett. 9(8), 1151-1154 (1999).