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1-Phenylethylamine

| 1-Phenylethylamine | α-Phenylethylamine | α-Methylbenzylamine | 1-PEA | α-PEA (S)-(−)- (CAS [2627-86-3])

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 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 monoamine oxidase inhibitor (MAOI), as well as an inhibitor of semicarbazide-sensitive amine oxidase (SSAO).

References

References

  1. John C. Robinson, Jr. and H. R. Snyder. (1943). "α-Phenylethylamine".
  2. (1960). "Practical Organic Chemistry, 4th Ed.". Longman.
  3. A. W. Ingersoll. (1937). "d- and l-α-Phenylethylamine". Organic Syntheses.
  4. (January 2004). "Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives". Neurotoxicology.
  5. (June 1986). "Studies of monoamine oxidase and semicarbazide-sensitive amine oxidase. II. Inhibition by alpha-methylated substrate-analogue monoamines, alpha-methyltryptamine, alpha-methylbenzylamine and two enantiomers of alpha-methylbenzylamine". Jpn J Pharmacol.
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