2-Chloro-2-phenylethylamine
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| IUPAC name
2-chloro-2-phenylethanamine
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Other names
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C8H10ClN | |
| Molar mass | 155.63 g·mol−1 |
| Density | 1.106 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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2-Chloro-2-phenylethylamine, also known as β-chlorophenethylamine, is an irreversible inhibitor or suicidal inhibitor of the enzyme dopamine-beta-monooxygenase,[1] 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,[2][3][4] 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.[4][5]
See also
References
- ^ 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". The Journal of Biological Chemistry. 265 (10): 5640–5647. ISSN 0021-9258. PMID 2318829.
- ^ Weyler, W. "2-Chloro-2-phenylethylamine as a mechanistic probe and active site-directed inhibitor of monoamine oxidase from bovine liver mitochondria". Archives of Biochemistry and Biophysics. 255 (2): 400–408. doi:10.1016/0003-9861(87)90408-5. ISSN 0003-9861. PMID 3592682.
- ^ PubChem. "2'-Chlorophenethylamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-07.
- ^ a b Mangold, J. B.; Klinman, J. P. (1984-06-25). "Mechanism-based inactivation of dopamine beta-monooxygenase by beta-chlorophenethylamine". The Journal of Biological Chemistry. 259 (12): 7772–7779. ISSN 0021-9258. PMID 6547439.
- ^ 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". Journal of Biological Chemistry. 265 (10): 5640–5647. doi:10.1016/S0021-9258(19)39410-4. ISSN 0021-9258.