Formation of 2-amino-3,7,8-trimethylimidazo [4,5-f]quinoxaline, a new mutagen, by heating a mixture of creatinine, glucose and glycine.
When a mixture of creatinine, glycine and glucose was heated for 2 h at 128 degrees 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-f]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-f]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 microgram, induced 163 000 and 9900 revertants of Salmonella typhimurium TA98 and TA100, respectively, with S9 mix.
D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D003404:Creatinine; D005947:Glucose; D005998:Glycine; D006358:Hot Temperature; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009152:Mutagenicity Tests; D009153:Mutagens / Q000138:chemical synthesis*; D009154:Mutation; D011804:Quinolines / Q000633:toxicity; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000633:toxicity; D012486:Salmonella typhimurium / Q000187:drug effects; D013056:Spectrophotometry, Ultraviolet
D009153:Mutagens; D011804:Quinolines; D011810:Quinoxalines; C042052:2-amino-3,7,8-trimethylimidazo(4,5-f)quinoxaline; D003404:Creatinine; C036989:2-amino-3,4-dimethylimidazo(4,5-f)quinoline; D005947:Glucose; D005998:Glycine