Identification of 2-amino-1,7-dimethylimidazo[4,5-g]quinoxaline: an abundant mutagenic heterocyclic aromatic amine formed in cooked beef.

ABSTRACT: A previously unknown isomer of the carcinogenic heterocyclic aromatic amine (HAA) 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (8-MeIQx) was recently discovered in the urine of meat eaters and subsequently detected in cooked ground beef (Holland, R.D., et al. (2004) Chem. Res. Toxicol. 17, 1121-1136). In this current investigation, the identity of the analyte was determined through a comparison of its chromatographic tR by HPLC and through UV and mass spectral comparisons to the synthesized isomers of 8-MeIQx. Angular tricyclic isomers of 8-MeIQx were excluded as potential structures of the newly discovered HAA, on the basis of dissimilar tR and product ion mass spectral data. The linear tricyclic isomers 2-amino-1,6-dimethylimidazo[4,5-g]quinoxaline (6-MeIgQx) and 2-amino-1,7-dimethylimi

SUBMITTER: Turesky RJ 

PROVIDER: S-EPMC2533101 | biostudies-literature | 2007 Mar

REPOSITORIES: biostudies-literature