Formation of 2-amino-3,7,8-trimethylimidazo[4,5-ƒ]quinoxaline, a new mutagen, by heating a mixture of creatinine, glucose and glycine

Abstract When a mixture of creatinine, glycine and glucose was heated for 2 h at 128°C in diethylene glycol containing 14% water, two mutagens were formed. One of them, responsible for 90% of the mutagenicity, has already been identified as 2-amino-3,8-dimethylimidazo[4,5-ƒ]quinoxaline (MeIQx). The other mutagen was purified and characterized. The UV absorption, mass and NMR spectra suggested that this mutagen was 2-amino-3,7,8-trimethylimidazo[4,5-ƒ]quinoxaline (7,8-DiMeIQx). Comparison of the spectral properties of the compound obtained from the heated model mixture with those of synthetic material confirmed this structure. 7,8-DiMeIQx is a newly identified compound which, at a dose of 1 μg, induced 163 000 and 9900 revertants of Salmonella typhimurium TA98 and TA100, respectively, with S9 mix.