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1-Phenylethylamine

1-Phenylethylamine (1-PEA or α-PEA), also known as α-methylbenzylamine, is the organic compound with the formula C<sub>6</sub>H<sub>5</sub>CH(NH<sub>2</sub>)CH<sub>3</sub>. 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 is used to resolve 1-Phenylethylamine, a versatile resolving agent in its own right. 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

References