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:[1]

C6H5C(O)CH3 + NH3 + H2 → C6H5CH(NH2)CH3 + H2O

The Leuckart reaction, using ammonium formate, is another method for this transformation.[2]

L-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.[3]

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).[4][5]

See also

References

  1. ^ John C. Robinson, Jr. and H. R. Snyder (1943). "α-Phenylethylamine". Organic Syntheses. 23: 68. doi:10.15227/orgsyn.023.0068.
  2. ^ Mann, F. G.; Saunders, B. C. (1960). Practical Organic Chemistry, 4th Ed. London: Longman. pp. 223–224. ISBN 9780582444072.
  3. ^ A. W. Ingersoll (1937). "d- and l-α-Phenylethylamine". Organic Syntheses. 17: 80. doi:10.15227/orgsyn.017.0080.
  4. ^ Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T (January 2004). "Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives". Neurotoxicology. 25 (1–2): 223–232. Bibcode:2004NeuTx..25..223N. doi:10.1016/S0161-813X(03)00101-3. PMID 14697897.
  5. ^ Arai Y, Toyoshima Y, Kinemuchi H (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. 41 (2): 191–197. doi:10.1254/jjp.41.191.
Allikas: https://en.wikipedia.org/wiki/1-Phenylethylamine
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