N,N-Dimethyl-2-chloro-2-phenylethylamine

N,N-Dimethyl-2-chloro-2-phenylethylamine (DMEA) is chemical compound that irreversibly inhibits the enzyme acetylcholinesterase. DMEA can cause intoxication in cats, resulting in respiratory failure to death, and progressive damage to the central nervous system in rats. Synthesis of DMEA can be obtained by treating N,N-dimethyl-2-hydroxy-2-phenylethylamine with thionyl chloride (SOCl2).

DMEA, when dissolved water, decomposes into a highly reactive aziridinium ion, N,N-dimethyl-2-phenylaziridinium (DPA). DPA binds to the anionic site of acetylcholinesterase, where it alkylates and irreversibly inhibits the enzyme.

DMEA has been compared to N,N-dimethyl-2-chloro-2-phenyl-1-methylethyl-amine (M-DMEA) and the results show that there is a difference between the degree of adrenergic blocking activity and their immonium ring stability in vitro.