Mutagenicity of Quinoline Derivatives and Analogs—Quinoxaline 1,4-Dioxide is a Potent Mutagen

Quinoline derivatives and analogs were surveyed for their mutagenicity using the Salmonella/microsome assay. 4-Methylquinoline, 4-methylquinoline 1-oxide, quinoxaline 1-oxide, quinoxaline 1,4-dioxide, 2,3-dimethylquinoxaline 1,4-dioxide, benzo[f]quinoline, l-methylbenzo[f] quinoline, and 4-methylbenzo[h]quinoline were mutagenic on S. typhimu-rium TA 100 in the presence of the rat liver 9000 Xg supernatant (“S-9 mix”). Quinoxaline 1- oxide, quinoxaline 1,4-dioxide, and 2,3-dimethylquinoxaline 1,4-dioxide were also mutagenic on TA 100 in the absence of S-9 mix. 2-Methylquinoxaline was mutagenic on strain TA 98 in the presence of S-9 mix. Among these mutagenic compounds, quinoxaline 1,4-dioxide was the strongest mutagen. The following compounds showed no significant mutagenicity on TA 98 and TA 100 both in the presence and absence of S-9 mix: 2- methylquinoline, 2,4-dimethylquinoline, quinoline-2-carboxamide, 4-methylquinoline-2-carboxamide, N-methylquinoline-2-carboxamide, N,4-dimethylquinoline-2-carboxamide, 2-(2-pyrazinyl)quinoline, 2-(5-pyrimidinyl)quinoline, benzo[h] quinoline, 1,10-phenanthroline, quinoline 1-oxide, 2-methylquinoline 1-oxide, 2,4-dimethylquinoline 1-oxide, isoquinoline, 3-methylisoquinoline, isoquinoline-1-carboxamide, 4-chloroquinazoline, quinoxaline, 2,3-dimethylquinoxaline, 3-methylquinoxaline-2-carboxamide, 2,3-bis(2-pyridyl)-quinoxaline and acridine.