Aromatic amine heterocyclic

UK Ministry of Agriculture Fisheries and Food and Flealth and Safety Executive, Annual Report of the Working Party on Pesticide Residues in Food (1997), MAFF Publications, London, 1997. lARC, Monographs on the Evabiation of the Carcinogenic Risk of Chemicals to Hnmans Volume 56 Some Naturally Occurring Substances Food Items and Constituents, Heterocyclic Aromatic Amines and Mycotoxins, WFIO, Geneva, 1979, p. 397. 

BRITT c, GOMAA E A, GRAY j I and BOOREN A M (1998) Influence of cherry tissue on lipid oxidation and heterocyclic aromatic amine formation in groimd beef patties, JAgric Food Chem, 46, 4891-7. 

With aliphatic amines, the decomposition catalysis is moderate with heterocyclic aromatic amines (pyridine, quinoline), 0.1 % of amine is sufficient to cause maleic anhydride to decompose. An accident has also been mentioned with NaOH. This decomposition also takes place in the presence of sodium, lithium, ammonium, potassium, calcium, barium, magnesium and beryllium cations. 

Oxidation of heterocyclic aromatic amines, N-oxide reduction... 

Some Naturally Occurring Substances Food Items and Constituents, Heterocyclic Aromatic Amines and Mycotoxins... 

Imidazole and its derivatives form an interesting and important class of heterocyclic aromatic amines. Imidazole is approximately 100 times more basic than pyridine. 

IARC. Some naturally occurring substances food items and constituents, heterocyclic aromatic amines and mycotoxins. Monographs on the evaluation of carcinogenic risks to humans. 56 489-521, 1993. 

Some Naturally Occurring Substances. Food Items and Constituents, Heterocyclic Aromatic Amines and Mycotoxins (IARC Monographs on the Evaluations of Carcinogenic Risks to Humans), No. 56, International Agency for Research on Cancer, Lyon, 1993, pp. 489-521. 

Murray S, Lake BG, Gray S, Edwards AJ, Springall C, Bowey EA, Williamson G, Boobis AR, Gooderham NJ. Effect of cruciferous vegetable consumption on heterocyclic aromatic amine metabolism in man. Carcinogenesis 2001 22 1413-1420. 

Structures 6.1 Structures of some heterocyclic aromatic amines... 

S. Zochling, and M. Murkovic, Formation of the heterocyclic aromatic amine PhIP Idenfication of precursors and intermediates, Food Chem., 2002, 79, 125-134. 

B. Zimmerli, P. Rhyn, O. Zoller, and J. Schlatter, Occurrence of heterocyclic aromatic amines in the Swiss diet analytical method, exposure estimation and risk assessment, Food Add. Contam., 2001, 18, 533-551. 

R. D. Klassen, D. Lewis, B. P.-Y. Lau, and N. P. Sen, Heterocyclic aromatic amines in cooked hamburgers and chicken obtained from local fast food outlets in the Ottawa region, Food Res. Int., 2002, 35, 837-847. 

Figure 13.10. NAT-mediated metabolic activation of heterocyclic aromatic amines. 2-AF is not a NAT substrate for A-aectylation (compare with 2-NA, 4-ABP A-acetylation in Figure 13.9). 2-AF is detoxified by P4502B1 ring hydroxylation. 2-AF is also metabolized via P4501A2-mediated A-hydroxylation. The resultant A-hydroxy 2-AF is a good substrate of conjugation reactions by NATs as well as by UGTs and SULTs and is converted to reactive metabolites for DNA adduct formation.

Tavan, E., Cayuela, C., et al. Effects of dairy products on heterocyclic aromatic amine-induced rat colon carcinogenesis. Carcinogenesis 23(3), 477-483, 2002. 

Krul, C. A. M., Luiten-Schuite, A., Baan, R., Verhagen, H., Mohn, G., Feron, V., and Havenaar, R. (2000), Application of a dynamic in vitro gastrointestinal tract model to study the availability of food mutagens, using heterocyclic aromatic amines as model compounds, Food Chem. Toxicol., 38,783-792. 

In a similar way, the use of formic acid/ammonium formate was shown to be superior to the use of acetic acid/ammonium acetate in the RP HPLC-ESI MS/MS analysis of a number of heterocyclic aromatic amines [7]. It is clear from numerous other examples in the literature that HPLC resolution and MS sensitivity can be dramatically influenced by the correct selection of mobile phases, organic modifiers, and ion-pairing additives. 

Rivera, L., Curto, M. J. C., Pais, P., Galceran, M. T. Puignou, L. (1996). Solid-phase extraction for the selective isolation of polycyclic aromatic hydrocarbons, azaarenes and heterocyclic aromatic amines in charcoal-grilled meat. Journal of Chromatography A, 731, 85-94. 

Bianchi, F. et al. Investigation of the separation of heterocyclic aromatic amines by reversed phase ion-pair hquid chromatography coupled with tandem mass spectrometry the role of ion-pair reagents on LC-MS/MS sensitivity. J. Chromatogr. B. 2005, 825, 193-200. 

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