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Conversion of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (mptp) and its 5-methyl analog into pyridinium salts

✍ Scribed by Wieslaw Gessner; Arnold Brossi; Rong-Sen Shen; Richard R. Fritz; Creed W. Abell

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
383 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Monoamine oxidase B metabolizes 1‐methyl‐4‐phenyl‐1,2,3,6‐tetrahydropyridine (MPTP; 1) first to 1‐methyl‐4‐phenyl‐2,3‐dihydropyridinium salt (MPDP^+^; 5), and then to 1‐methyl‐4‐phenylphridinium salt (MPP^+^; 7). Chemical synthesis of MPDP^+^ and its 5‐methyl analog 6 was accomplished from the N‐oxides 3 and 4 of MPTP and its 5‐methyl analog, respectively, by a Polonovski reaction. Oxidation of MPDP^+^ to MPPM^+^ was accomplished with air, and greatly accelerated by Pt catalyst. Reduction of MPDP^+^ and MPP^+^ with NaBH~4~ afforded MPTP.

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Primary cultures of mouse astrocytes were treated with both the monoamine oxidase (MAO) A inhibitor, clorgyline, and the MA0 B inhibitor, deprenyl, prior to the addition of the neurotoxicant 1 -methyl-4-phenyl-l,2,3,6-tetrahydropyridine (MPTP). Production of the 1-methyl-4-phenylpyridinium (MPP+) to