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

Names
IUPAC name 2-Chloro-N,N-dimethyl-2-phenylethanamine
Identifiers
CAS Number	6407-17-6
3D model (JSmol)	Interactive image
ChemSpider	180619
PubChem CID	208446
UNII	F2WN67C3SK
CompTox Dashboard (EPA)	DTXSID101283012
InChI InChI=1S/C10H14ClN/c1-12(2)8-10(11)9-6-4-3-5-7-9/h3-7,10H,8H2,1-2H3Key: BHDHMUNVUMGSIY-UHFFFAOYSA-N
SMILES CN(C)CC(c1ccccc1)Cl
Properties
Chemical formula	C10H14ClN
Molar mass	183.68 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

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.

See also

• Acetylcholinesterase inhibitor

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. 100 (1): 100–114. ISSN 0022-3565. PMID 14774797.
2. ^ Kreienkamp, HJ; Weise, C; Raba, R; Aaviksaar, A; Hucho, F (15 July 1991). "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. 88 (14): 6117–21. Bibcode:1991PNAS...88.6117K. doi:10.1073/pnas.88.14.6117. PMC 52033. PMID 2068091.
3. Weise, C; Kreienkamp, HJ; Raba, R; Pedak, A; Aaviksaar, A; Hucho, F (December 1990). "Anionic subsites of the acetylcholinesterase from Torpedo californica: affinity labelling with the cationic reagent N,N-dimethyl-2-phenyl-aziridinium". The EMBO Journal. 9 (12): 3885–8. doi:10.1002/j.1460-2075.1990.tb07607.x. PMC 552156. PMID 2249655.
4. Ferguson, F. C. (1958-11-01). "Relation of Ethyleneimmonium Ring Stability to Adrenergic Blocking Activity in Two Haloalkylamines". Experimental Biology and Medicine. 99 (2): 362–365. doi:10.3181/00379727-99-24351. ISSN 1535-3702. PMID 13601871. S2CID 34000963.

• Acetylcholinesterase inhibitors
• Nitrogen mustards
• Phenethylamines
• Organochlorides