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

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.^[1] 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.^{[2] [3]}

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.^[4]

See also

• Acetylcholinesterase inhibitor

Notes and References

1. Ferguson . Frank C. . Wescoe . W. Clarke . 1950-09-01 . The Pharmacology of N,n-Dimethyl 2-Chloro-2-Phenylethylamine . Journal of Pharmacology and Experimental Therapeutics . en . 100 . 1 . 100–114 . 0022-3565 . 14774797.
2. Weise . C . Kreienkamp . HJ . Raba . R . Pedak . A . Aaviksaar . A . Hucho . F . Anionic subsites of the acetylcholinesterase from Torpedo californica: affinity labelling with the cationic reagent N,N-dimethyl-2-phenyl-aziridinium. . The EMBO Journal . December 1990 . 9 . 12 . 3885–8 . 2249655 . 552156. 10.1002/j.1460-2075.1990.tb07607.x .
3. Kreienkamp . HJ . Weise . C . Raba . R . Aaviksaar . A . Hucho . F . Anionic subsites of the catalytic center of acetylcholinesterase from Torpedo and from cobra venom. . Proceedings of the National Academy of Sciences of the United States of America . 15 July 1991 . 88 . 14 . 6117–21 . 2068091 . 52033. 10.1073/pnas.88.14.6117 . 1991PNAS...88.6117K . free .
4. Ferguson . F. C. . 1958-11-01 . Relation of Ethyleneimmonium Ring Stability to Adrenergic Blocking Activity in Two Haloalkylamines. . Experimental Biology and Medicine . en . 99 . 2 . 362–365 . 10.3181/00379727-99-24351 . 13601871 . 34000963 . 1535-3702.