2- Phenylcyclopropylamine, monoamine oxidase

Table 4. IC50 values and inhibition type of 2-fluoro-2-phenylcyclopropylamines for recombinant human liver monoamine oxidases (MAO) A and [134a], Adapted by permission of Elsevier Ltd. Copyright 2004.

For some years the mitochondrial flavoenzyme monoamine oxidase (MAO) was the target of selective inhibition in the development of tranquillizing drugs " One potent inhibitory class was that of cyclopropylamines of which tranylcypramine (164) (trans-2-phenylcyclopropylamine) was a successful, albeit clinically dangerous and eventually unusable agent °. Tranylcypramine (164) and analogous cyclopropylamines turn out to... 

The most outstanding effect of rrans-2-phenylcyclopropylamine (5) (generic names tranylcypromine, transamine) is the inhibition of monoamine oxidase (MAO) ... 

For reviews see. (a) Welch, J. T. (1987) Tetrahedron report number 221 Advances in the preparation of biologically active organofluorine compounds. Tetrahedron, 43, 3123-3197. (b) Resnati, G. (1993) Synthesis of chiral and bioactive fluoroorganic compounds, Tetrahedron, 49, 9385-9445. (c) Soloshonok, V. A. (ed.) (1999) Enantiocontrolled Synthesis of Fluoroorganic Compounds Stereochemical Challenges and Biomedicinal Targets, John Wiley Sons, Ltd, Chichester, UK. (d) Rosen, T. C., Yoshida, S., Kirk, K. L. and Haufe, G. (2004) Fluorinated phenylcyclopropylamines as inhibitors of monoamine oxidases. ChemBioChem., 5, 1033-1043. 

Song, Y., Yoshida, S., Frohlich, R., et al. (2005) Fluorinated phenylcyclopropylamines. Part 4 Effects of aryl substituents and stereochemistry on the inhibition of monoamine oxidases by... 

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