Organic N-Chloramines: Chemistry and Toxicology

The stability of aqueous solutions of organic N-chloramines, suspected of contaminating chlorinated water, has been studied. Two factors influence the decomposition of solutions of N-chloropiperidine and N-chlorodiethylamine: a spontaneous decomposition and photodecomposition. Since solutions of these compounds are relatively long-lived, a need for an analytical method for their identification is discussed. A new method is described which involves reaction of organic N-chloramines with arenesulfinic acid salts. The method gives high yields of stable arenesulfonamides. Several toxicological studies of N-chloropiperidine are described. The compound is mutagenic by Ames assay in Salmonella typhimurium strain TA 100 and does not require metabolic activation as indicated in a total body fluids analysis using C57BL/J6 mice. N-Chloropiperidine was subjected to a modified in vitro cell transformation assay using diploid fibroblast cells from Syrian hamster fetuses. A maximum number of foci of 4 per dish was observed at a seeding of 5 X 10(3) cells/60 mm dish. Under similar conditions, MNNG-induced foci ranged from 4 to 7 per dish.