Mutagenicity and chemistry of N-nitroso-N-(p-substituted-benzyl)methylamines

The relative mutagenicities of N-nitroso-N-(p-substituted-benzyl)methylamines in Salmonella typhimurium TA 1535 were tested in order to determine whether biological activity is affected by the electron density at a nitrosamine alpha carbon. The order of potency was as follows: X = Cl greater than CN greater than Br greater than NO2 greater than H greater than CH3O greater than CH3 greater than F much greater than COOH. No direct correlation was apparent, nor was there any obvious correlation between biological activity and the extent of base-catalyzed hydrogen-deuterium exchange at the alpha carbons.