Wiki Article
2-chloro-2-phenylethylamine
Nguồn dữ liệu từ Wikipedia, hiển thị bởi DefZone.Net
 | |
| Names | |
|---|---|
| IUPAC name
2-chloro-2-phenylethanamine
| |
Other names
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
PubChem CID
|
|
| |
| |
| 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).
| |
2-chloro-2-phenylethylamine also known as β-Chlorophenylethylamine — irreversible inhibitor or suicidal inhibitor of the enzyme monoamine oxidase B (MAO-B)[1], irreversible inhibitor of dopamine-beta-monooxygenase[2], 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[3][4][5], does not exhibit pronounced psychoactivity.
It is a related compound to N,N-Dimethyl-2-chloro-2-phenylethylamine (DMEA), is a precursor in organic synthesis.
Pharmacology
[edit]inhibition of monoamine oxidase B
[edit]the compound It is classified as a non-medical use, selective inhibitor of monoamine oxidase B (MAO-B) that acts as a "suicide inhibitor" by covalently modifying the active site of the enzyme and completely blocking its catalytic activity[3].
During a standard enzymatic reaction, MAO-B oxidizes the compound to 2-chloro-2-phenylacetaldehyde. The absence of significant amounts (less than 0.25 mol%) of 2-phenylacetaldehyde indicates that the reaction proceeds without the formation of a free carbanion at the C-1 atom.[3]
The mechanism of inactivation depends on the environment: under aerobic conditions, the enzyme is covalently modified by the oxidation product (2-chloro-2-phenylacetaldehyde), while under anaerobic conditions, inactivation occurs through direct alkylation by the parent compound.[1]
inhibition of Dopamine β-hydroxylase
[edit]2-Chloro-2-phenylethylamine is a suicide inhibitor of dopamine beta-monooxygenase (Dopamine β-hydroxylase), which irreversibly inactivates them via covalent modification of the active site: in the case of MAO-B, through direct alkylation or the effect of an aldehyde product; and in the case of dopamine beta-hydrooxygenase, a bound alpha-aminoacetophenone is formed, followed by an intramolecular redox reaction to form a ketone-derived radical cation as an inhibitory substance [5][6].
See also
[edit]Referens
[edit]- ^ a b Weyler, Walter (1987-06-01). "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.
- ^ 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.
- ^ a b c 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.