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| Names | |
|---|---|
| IUPAC name 2-chloro-2-phenylethanamine | |
Other names
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| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
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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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
2-chloro-2-phenylethylamine also known asβ-Chlorophenylethylamine —irreversible inhibitor orsuicidal inhibitor of theenzymemonoamine oxidase B (MAO-B)[1], irreversible inhibitor ofdopamine-beta-monooxygenase[2], aderivative ofphenylethylamine in which thehydrogen atom in theβ-position of theethyl chain is replaced by achlorine atom, This is asubstituted phenylethylamine[3][4][5], does not exhibit pronouncedpsychoactivity.
It is a related compound toN,N-Dimethyl-2-chloro-2-phenylethylamine (DMEA), is aprecursor inorganic synthesis.
the compound It is classified as a non-medical use, selectiveinhibitor ofmonoamine oxidase B (MAO-B) that acts as a "suicide inhibitor" bycovalently modifying theactive site of theenzyme and completely blocking itscatalytic activity[3].
During a standardenzymatic reaction,MAO-Boxidizes 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 freecarbanion at the C-1 atom.[3]
The mechanism of inactivation depends on the environment: under aerobic conditions, theenzyme iscovalently modified by theoxidation product (2-chloro-2-phenylacetaldehyde), while underanaerobic conditions, inactivation occurs through directalkylation by the parent compound.[1]
2-Chloro-2-phenylethylamine is asuicide inhibitor of dopamine beta-monooxygenase (Dopamine β-hydroxylase), which irreversiblyinactivates them via covalent modification of theactive site: in the case ofMAO-B, through directalkylation or the effect of analdehyde product; and in the case of dopamine beta-hydrooxygenase, a boundalpha-aminoacetophenone is formed, followed by an intramolecularredox reaction to form aketone-derived radical cation as an inhibitory substance[5][6].