2-Chloro-2-phenylethylamine

β-Chlorophenethylamine Β-Chlorophenethylamine.svg skin-invert-image 200px β-Chlorophenylethylamine 2'-Chlorophenethylamine 2-chloro-2-phenylethanamine 4633-92-5 74986 99095 C1=CC=C(C=C1)C(CN)Cl InChI=1S/C8H10ClN/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8H,6,10H2 IUAYUYABWKLCER-UHFFFAOYSA-N 8 10 1 1 1.106 2-Chloro-2-phenylethylamine, also known as β-chlorophenethylamine, is an irreversible inhibitor or suicidal inhibitor of the enzyme dopamine-beta-monooxygenase,Bossard M. J. Klinman J. P. 1990-04-05 Use of isotope effects to characterize intermediates in mechanism-based inactivation of dopamine beta-monooxygenase by beta-chlorophenethylamine https://pubmed.ncbi.nlm.nih.gov/2318829 The Journal of Biological Chemistry 265 10 5640–5647 0021-9258 2318829 a derivative of phenylethylamine in which the hydrogen atom in the β-position of the ethyl chain is replaced by a chlorine atom. This is a substituted phenylethylamine,Weyler W. 2-Chloro-2-phenylethylamine as a mechanistic probe and active site-directed inhibitor of monoamine oxidase from bovine liver mitochondria https://pubmed.ncbi.nlm.nih.gov/3592682 Archives of Biochemistry and Biophysics 255 2 400–408 10.1016/0003-9861(87)90408-5 0003-9861 3592682PubChem 2'-Chlorophenethylamine https://pubchem.ncbi.nlm.nih.gov/compound/99095 2026-02-07 pubchem.ncbi.nlm.nih.gov enMangold J. B. Klinman J. P. 1984-06-25 Mechanism-based inactivation of dopamine beta-monooxygenase by beta-chlorophenethylamine https://pubmed.ncbi.nlm.nih.gov/6547439 The Journal of Biological Chemistry 259 12 7772–7779 0021-9258 6547439 does not exhibit pronounced psychoactivity. It is a related compound to N,N-dimethyl-2-chloro-2-phenylethylamine (DMEA), a precursor in organic synthesis. Pharmacology Inhibition of dopamine β-hydroxylase 2-Chloro-2-phenylethylamine is a suicide inhibitor of dopamine β-hydroxylase, which irreversibly inactivates them via covalent modification of the active site: a bound alpha-aminoacetophenone is formed, followed by an intramolecular redox reaction to form a ketone-derived radical cation as an inhibitory substance.Bossard M J Klinman J P 1990-04-05 Use of isotope effects to characterize intermediates in mechanism-based inactivation of dopamine beta-monooxygenase by beta-chlorophenethylamine. https://www.sciencedirect.com/science/article/pii/S0021925819394104 Journal of Biological Chemistry 265 10 5640–5647 10.1016/S0021-9258(19)39410-4 0021-9258 free See also N,N-Dimethyl-2-chloro-2-phenylethylamine References Category:Dopamine beta hydroxylase inhibitors Category:Monoamine oxidase inhibitors Category:Phenethylamines Category:Organochlorides