Structure-activity relationships for ulcerogenic and adrenocorticolytic effects of alkyl nitriles, amines, and thiols.
In rats, a single administration of acrylonitrile (vinyl cyanide) produces a rapidly occurring bilateral adrenal apoplexy. Structure-activity studies have shown that a close derivative, propionitrile (ethyl cyanide), causes duodenal ulcer without markedly affecting the adrenal glands. Prolonging the two-carbon chain of propionitrile by a methyl group (n-butyronitrile) enhances, replacing the methyl by bromide or nitrile decreases, while substitution by an amino group abolistes the ulcerogenic potency and variably affects the adrenocorticolytic action. On assaying a large number of nonnitrile compounds as well for ulcerogenic effect, such as thiols and amines, this effect was found to be related to a two-carbon structure bearing electronegative radicals on one or both ends of the chain.
D000303:Adrenal Cortex Diseases / Q000139:chemically induced*; D000307:Adrenal Gland Diseases / Q000139:chemically induced*; D000588:Amines / Q000633:toxicity*; D000818:Animals; D004381:Duodenal Ulcer / Q000139:chemically induced*; D005260:Female; D009570:Nitriles / Q000633:toxicity*; D051381:Rats; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds / Q000633:toxicity*
D000588:Amines; D009570:Nitriles; D013438:Sulfhydryl Compounds