Deamination of aliphatic amines by type B monoamine oxidase and semicarbazide-sensitive amine oxidase; pharmacological implications

  • P. H. Yu
  • B. A. Davis
  • A. A. Boulton
  • D. M. Zuo
Conference paper
Part of the Journal of Neural Transmission book series (NEURAL SUPPL, volume 41)


Straight and branched chain aliphatic monoamines, which are not normal tissue constituents, are deaminated selectively by type B monoamine oxidase (MAO-B). They exhibit a high affinity towards the active site of MAO-B and this made them very useful pharmacologically. An anticon-vulsant prodrug, Milacemide [2-(N-pentyl)glycinamide] is deaminated by MAO-B and this facilitates a mechanism of delivering glycine into the CNS. We have found that 2-propyl-pentylamine (2-propyl-1-aminopentane) and N-(2-propylpentyl)glycinamide are also converted by MAO-B to valproic acid and glycine both in vitro and in vivo; these compounds, however, cause severe tremor. By attaching a propargylamine group the resultant series of aliphatic propargylamine derivatives have been shown to be very potent selective MAO-B inhibitors. They are chemically quite different from most other MAO-B inhibitors, since they do not possess any aromatic structures. The relatively short chain aliphatic propargylamines, i.e. N-2-pentyl-N-methylpropargylamine and N-2-hexyl-N-methylpropargylamine, are 4 to 5 times more potent and more selective than selegiline (1-deprenyl) with respect to the inhibition of MAO-B in brain following oral administration.


Monoamine Oxidase Aliphatic Amine Amine Oxidase Carbon Chain Length SSAO Activity 


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Copyright information

© Springer-Verlag 1994

Authors and Affiliations

  • P. H. Yu
    • 1
  • B. A. Davis
    • 1
  • A. A. Boulton
    • 1
  • D. M. Zuo
    • 1
  1. 1.Neuropsychiatric Research Unit, Department of PsychiatryUniversity of SaskatchewanSaskatoonCanada

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