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 language | English (US) |
|---|---|
| Pages (from-to) | 1953-1957 |
| Number of pages | 5 |
| Journal | Journal of Medicinal Chemistry |
| Volume | 28 |
| Issue number | 12 |
| DOIs | |
| State | Published - Dec 1985 |
ASJC Scopus subject areas
- Molecular Medicine
- Drug Discovery