1-Phenylethylamine (1-PEA or α-PEA), also known as α-methylbenzylamine, is the organic compound with the formula C6H5CH(NH2)CH3. This primary amine is a colorless liquid is often used in chiral resolutions. Like benzylamine, it is relatively basic and forms stable ammonium salts and imines.
Preparation and optical resolution 1-Phenylethylamine may be prepared by the reductive amination of acetophenone:
The Leuckart reaction, using ammonium formate, is another method for this transformation.
-malic acid, a versatile resolving agent in its own right, is used to resolve 1-Phenylethylamine. The dextrorotatory enantiomer crystallizes with the malate, leaving the levorotatory form in solution.
Pharmacology Similarly to benzylamine and analogues like pargyline, 1-phenylethylamine has been found to act as a very weak monoamine oxidase inhibitor (MAOI), as well as an inhibitor of semicarbazide-sensitive amine oxidase (SSAO).
See also 2-Phenylethylamine
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