A TOXICOLOGICAL AND BIOCHEMICAL STUDY OF ω-FLUORO COMPOUNDS

Abstract

A series of ω-fluoro compounds have been examined for their toxicity to mice and their ability to cause accumulation of citric acid in vivo. It was found that the toxic members did cause citric acid accumulation. Since fluoroacetate causes citric acid accumulation, it was concluded that the activity of these compounds and their effect on citric acid levels is in agreement with the hypothesis that these compounds were degraded to a fluoroacetyl derivative. The findings suggested that mice can degrade to fluoroacetate, compounds containing the following terminal radicals: amine, nitro, nitrile, thiocyanate, isothiocyanate, mercaptan, fluoride, chloride, bromide, iodide, tosylate, mesylate, 2-ketone, sulphonyl chloride, 1-alkyne, ether, substituted urea, aldehyde, and carboxyl. When compared on a molar basis several of the toxic compounds containing four or more carbon atoms were more toxic than fluoroacetate. 6-Fluorohexylamiue and 6-fluorohexanoic acid, which were representative of this type of compound, were investigated in this regard. These compounds, like fluoroacetate, were not immediately reactive but appeared to be converted to the toxic end-product more efficiently. In the dog, death from 6-fluorohexylamine was due to respiratory failure.