STRUCTURAL CONSIDERATIONS IN THE METABOLISM OF NITRILES TO CYANIDE INVIVO

  • 1 January 1982
    • journal article
    • research article
    • Vol. 10  (5) , 495-498
Abstract
In order to investigate structure-activity relationships that influence metabolism of nitriles to CN-, thiocyanate was measured, as an index of CN- release, in urine of rats given equimolar doses of nitriles. Significantly more SCN- was excreted after oral than after i.p. administration of saturated (C2-C5) nitriles, but SCN- excretion was the same after both routes for n-hexanenitrile. Among saturated nitriles, SCN- excretion was maximal for the C3 and C4 compounds, propionitrile, n-butyronitrile and isobutyronitrile, after oral and i.p. administration. SCN- excretion was not elevated after administration of the tertiary nitrile trimethylacetonitrile. Administration (oral) of the unsaturated nitriles acrylonitrile, crotonitrile and 3-butenenitrile yielded 37, 5.6 and 29% of the dose as SCN-; after i.p. injection 4.5, 4.6 and 18% of the doses were excreted as SCN-, respectively. After i.v. injection of acrylonitrile, urinary SCN- content was not elevated; 45% of an i.v. dose of the saturated analog propionitrile was excreted as SCN-. Length of the C chain, presence of substituents at the .alpha.-C, position of double bonds and, for some compounds, route of administration, were important factors influencing the release of CN- from nitriles.