1-Benzylcyclopropylamine and 1-(Phenylcyclopropyl)methylamine: An Inactivator and a Substrate of Monoamine Oxidase

Richard B Silverman, Paul A. Zieske

Research output: Contribution to journalArticle

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)1953-1957
Number of pages5
JournalJournal of Medicinal Chemistry
Volume28
Issue number12
DOIs
StatePublished - Jan 1 1985

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ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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