arachidonoyl-2'-chloroethylamine

Arachidonoyl-2'-chloroethylamine (AC) is a synthetic small molecule analog of the endocannabinoid anandamide (AEA). It was developed to investigate the structural requirements for AEA-mediated cytotoxicity in cancer cells, specifically those overexpressing cyclooxygenase-2 (COX-2). The molecule features a substitution of the terminal hydroxyl group of the ethanolamine chain with a chlorine atom, a modification intended to enhance solubility and potentially alter its metabolic profile by resisting degradation by fatty acid amide hydrolase (FAAH). In preclinical research presented at AACR 2017, AC was tested against tumorigenic keratinocytes but failed to demonstrate significant anti-proliferative activity compared to other analogs like Arvanil or R1-methanandamide, leading to its exclusion from further metabolic studies in that specific research program.

Other names

N-(2-chloroethyl)arachidonylamide