1-Benzylcyclopropylamine and 1-(phenylcyclopropyl)methylamine: an inactivator and a substrate of monoamine oxidase.
1-Benzylcyclopropylamine (1) and 1-(phenylcyclopropyl)methylamine (2), cyclopropane analogues of phenethylamine, were tested as inactivators for monoamine oxidase (MAO). Compound 1 is a potent competitive reversible inhibitor of the oxidation of benzylamine and also is a mechanism-based inactivator. It requires 2.3 equiv of 1 to inactivate 1 equiv of MAO. The excess equivalents of 1 are converted into benzyl vinyl ketone. A one-electron mechanism of inactivation is proposed. Compound 2 is a substrate for MAO and is converted into 1-phenylcyclopropanecarboxaldehyde without inactivation of the enzyme. Mechanistic consequences are discussed as a result of this observation.
D001596:Benzylamines / Q000378:metabolism; D001667:Binding, Competitive; D055598:Chemical Phenomena; D002621:Chemistry; D003521:Cyclopropanes / Q000378:metabolism / Q000494:pharmacology*; D005182:Flavin-Adenine Dinucleotide / Q000378:metabolism; D007700:Kinetics; D008995:Monoamine Oxidase / Q000378:metabolism*; D008996:Monoamine Oxidase Inhibitors / Q000494:pharmacology*
D001596:Benzylamines; D003521:Cyclopropanes; D008996:Monoamine Oxidase Inhibitors; D005182:Flavin-Adenine Dinucleotide; C047294:1-benzylcyclopropylamine; C047295:1-(phenylcyclopropyl)methylamine; C030796:benzylamine; D008995:Monoamine Oxidase