Aromatic Amines and Amides

A2 Planar poly (hetero)-aromatic amines and amides Caffeine Furafulline TCDD, PAHs Many heterocyclic amines... 

Miller, J. A., Miller, E. C. The metabolic activation of carcinogenic aromatic amines and amides. Prog. Exp. Tumor Res. 2, 273 (1969). 

Nitrenium ions may occur during bioactivation of aromatic amines and amides, which are usuaUy A-oxidized into A-hydroxylated derivatives. By sulfation or esteriUca-tion foUowed by elimination of the newly formed leaving group, the latter may be transformed into highly reactive nitrenium ions. In the case of aromatic nitrenium ions they are in equiUbrium with their tautomeric aromatic carbocations, which react with ceUular nucleophiUc macromolecules (nucleic acids, etc.). 

BuiSnH, AIBN, benzene, reflux, 1-3.5 h. This method only cleaves Cbz groups from aromatic amines and amides. ... 

The FMO does not catalyze epoxidation reactions or hydroxylation at unactivated carbon atoms of xenobiotics. Primary aromatic amines and amides, aromatic heterocyclic amines and imines, and the aliphatic primary amine phentermine are N-oxidized by CYP450 to hydroxylamines. The CYP450 oxidizes carbon disulfide to carbon dioxide and hydrogen sulfide and the antipsychotic phenothiazines to sulfoxides. 

The metabolism of aliphatic and aromatic amines and amides was previously described in the report of the sixty-fifth meeting (Annex 1, reference 178). 

Table 1. Summary of the results of safety evaluations of aliphatic and aromatic amines and amides used as flavouring agents ... 

Table 1 summarizes the evaluations of the 12 aliphatic and aromatic amines and amides in this group. 

This monograph summarizes key aspects relevant to the safety evaluation of 12 flavouring agents that are additions to the aliphatic and aromatic amines and amides evaluated previously (see Table 1). The group contained one aliphatic amine six aliphatic amides, four of which contain ethanolamine and two of which contain ring structures and five aromatic amides, three of which contain oxalamide. 

Ford, G. P. and Scribner, J. D., MNDO molecular orbital study of nitrenium ions derived from carcinogenic aromatic amines and amides, /. Am. Chem. Soc., 103, 4281,1981. 

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