2-Amino-3,8-dimethylimidazo quinoxaline

In very heavily smoked products there may also be small amounts of HAs, usually less than 1 ng per g. The smoke-dried bonito (baikan) contains 2 to 3 ng HAs per g (Kikugawa et al., 1986). Smoke-dried mackerel, produced by smoke-drying at 80 to 140°C for two hours, repeated several times, has been found to contain 2-amino-3,8-dimethylimidazo[4,5-/ quinoxaline (0.8 ng per g), and a smaller quantity of 2-amino-3,4,8-trimethylimidazo[4,5-/ quinoxaline (ICato, Kikugawa and Hayatsu, 1986). 

Kato, T., Kikugawa, K. and Hayatsu, H. (1986). Occurrence of the mutagens 2-amino-3,8-dimethylimidazo[4,5-/ quinoxaline (MelQx) and 2-amino-3,4,8-trimethyli-midazo[4,5-/ quinoxaline (4,8-Me2lqx) in some Japanese smoked, dried fish products, /. Agric. Food Chem., 34, 810-814. 

Boyce A, Doehmer J, Gooderham NJ. 2004. Phytoalexin resveratrol attenuates the mutagenicity of the heterocyclic amines 2-amino-l-methyl-6-phenylimidazo [4,5-b]pyridine and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline. J Chromatogr B Analyt Technol Biomed Life Sci 802 217-223. 

L. M. Tikkanen, T. M. Sauri, and K. J. Latva-Kala, Screening of heat-processed Finnish foods for the mutagens 2-amino-3,4,8-dimethylimidazo[4,5-f]quinoxaline, 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, and 2-amino-l-methyl-6-phenylimidazo[4,5-b]pyri-dine, Food Chem. Toxic., 1993, 31, 717-721. 

Edenharder, R., Kurz, P., John, K., Burgard, S. and Seeger, K. (1 994) In vitro effect of vegetable and fruit juices on the mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline, 2-amino-3,4-dimethylimidazo[4,5-fjquinoline and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline. Food and Chemical Toxicology 32(5), 443 159. 

Langouet, S. Welti, D. H. Kerriguy, N. Fay, L. B. Huynh-Ba, T. Markovic, J. Guengerich, F. P. Guillouzo, A. Tur-esky, R. J. Metabolism of 2-Amino-3,8-dimethylimidazo[4,5-/ - quinoxaline in Human Hepatocytes 2-Amino-3-methy-limidazo[4,5/]quinoxaline-8-carboxylic Add Is a Major Detoxication Pathway Catalyzed by Cytochrome P450 1A2, Chem. Res. Toxicol. 2001, 14 (2), 211— 221. 

Figure 14.10 Structures of four of the most abundant HAA in cooked food. PhIP is 2-amino-l-methyl-6-phenylimidazo[4,5-6]pyridine, AocC is 2-amino-9/f-pyrido[2,3-Z)]indole, MelQx is 2-amino-3,8-dimethylimidazo[4,5-/]quinoxaline, and IFP is 2-amino-l,6-dimethylfuro[3,2-e]imidazo[4,5-6]pyridine.

Amino-l,3-dimethylimidazo[4,5-g]quinoxaline-2,4-dione (63) was obtained in 54% yield by the reductive cyclization of nitrohydrazine 62 (84JHC791). 

Gooderham N.J., Soames A., Rice J.C., Boobis A.R. and Davies D.S. Distribution and elimination of [2-14C]amino-3,8-dimethylimidazo[4,5-f] quinoxaline in mice. Human and Experimental Toxicology. 10,337.1991... 

Winton DJ, Gooderham NJ, Boobis AR, et al. 1990. Mutagenesis of mouse intestine in vivo using the Dlb-1 specific locus test studies with 1,2-dimethylhydrazine, dimethylnitrosamine, and the dietary mutagen 2-amino-3,8-dimethylimidazo[4,5-/ quinoxaline. Cancer Res 50 7992-7996. 

LOW-DOSE CARCINOGENICITY OF 2-AMINO-3,8-DIMETHYLIMIDAZO[4,5-f]QUINOXALINE (MeIQx) IN THE RAT LIVER... 

Murai, T, Mori, S., Kang, J. S., Morimura, K., Wanibuchi, H., Totsuka, Y., and Fukushima, S. (2008). Evidence of a threshold-effect for 2-amino-3,8-dimethylimidazo-[4,5-/ quinoxaline liver carcinogenicity in E344/DuCrj rats. Toxicol Pathol 36, 412-All. 

Y2. Yanagisawa, H., Manabe, S., Kitagawa, Y., et al., Present amino-3,8-dimethylimidazo [4,5-/]quinoxaline (MelOx) in dialysis patients with uremia. Biochem. Biophys. Res. Commun. 138, 1 (1986). 

Amino-3,4-dimethylimidazo[4,5-f] quinoline 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline... 

Three heterocyclic aromatic amines, 2-amino-3-methyl-imidazo[4, 5-f]quinoline (IQ),2-amino-3,4-dimethylimidazo[4,5-f]quinoxaline and 2-amino-3,4-dimethylimidazo[4,5-f]quinoline, have been found in boiled pork juice [109]. Six organosulfur compoimds - diallyl disulfide (DAD), dipropyl disulfide (DPD), diallyl sulftde (DAS), allyl methyl sulfide (AMS), allyl mercaptan (AM) and cysteine - were added separately to the pork juice before reflux boiling and then the mutagenicity of each sample was examined with the Salmonella typhimurium strain TA98 in the presence of S9 mix. All six compounds were found to inhibit the mutagenicity of boiled pork juice. The greatest inhibitory effect was observed with DAD and DPD, and this was 111-fold higher than that of... 

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