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, 1-methylbenzo [f] quinoline, and 4-methylbenzo [h] quinoline were mutagenic on S. typhimurium TA 100 in the presence of the rat liver 9000×g 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.