Amines, carcinogenic

The use in consumer products of azo dyes that yield carcinogenic amines under reductive conditions is illegal in Germany. Detection of such carcinogenic amines in textiles is problematic, and a method was proposed combining TLC, automatic multiple development... 

Fig. 3.69. Chemical structures of the azo colourants together with the released carcinogenic amines investigated in this study. Reprinted with permission from C. S. Eskilsson et al. [140].

C.S. Eskilsson, R. Davidson and L. Mathiasson, Harmful azo colorants in leather. Determination based on their cleavage and extraction of corresponding carcinogenic amines using modern extraction techniques. J. Chromatogr.A, 955 (2002) 215-227. 

NCTR. 1979. Metabolism of azo dyes to potentially carcinogenic amines. National Center for Toxicological Research Technical Report, Experiment No. 196. 

However, since that time it has been recognised that the list of potentially carcinogenic amines is much longer and that these amines could actually be regenerated by metabolic (or chemical) reductive cleavage of those dyes that are made using these particular amines as their diazo components. (Figure 2.9 for Cl Acid Red 21.)... 

Table 8.4 lists the carcinogenic amines according to TRGS 614 (Limitation of use of dyes which are likely to cleave into carcinogenic aromatic amines) (March 2001) [36], which are classified as carcinogenic by TRGS 905 and 67/548/EEC Annex 1. 

The presence and amount of the carcinogenic amines are to be tested according to an official German test method [44], The test result leads to banning of the article if the trace amount of a listed amine exceeds 30 ppm. 

Biphenyldiamine NHj Not carcinogenic Amine group in 2 position missing 4-position... 

Carcinogenic amines are converted biochemically to A-hydroxyaryl amines, mainly in the liver, but also in erythrocytes, the intestine and other organs. This first, or initial,... 

The substrates of acetylation, schematized in Fig. 13.25, are mainly amines of medium basicity. Very few basic amines (primary or secondary) of medicinal interest have been reported to form N-acetylated metabolites (reaction 1), and when they did, the yields were low. In contrast, a large variety of primary aromatic amines are N-acetylated (reaction 2). Thus, several dmgs such as sulfonamides and para-aminosalicylic acid (30) (PAS Fig. 13.26) are acetylated to large extents, not to mention various carcinogenic amines such as benzidine. 

HPLC has also been applied to the analysis of trimethylolpropane and pentaerythritols in industrial synthesis solutions, 2-mercaptobenzothiazole in waste dump effluent, polythionates in mining waste water, isocyanates in working atmospheres, carcinogenic amines, aniline in waste water, polyethylene oxide fatty acid surfactants in industrial process waters and phthalate esters in river water. 

Because of their carcinogenicity, amines have to be monitored. For example, primary aromatic amines (PAAs) are substances that can be transferred from food packaging materials into foodstuffs. In the production of multilayer plastic materials it is common to use reactive adhesive mixtures containing aromatic isocyanate monomers. In cases of incomplete curing, residues of the aromatic isocyanates react with water to produce PAAs. Some of these amines, including... 

On the basis of quantitative data for aromatic amines in cigarette smoke, an etiological significance of these traces of carcinogenic amines in bladder cancer is questionable, even if one were to consider the total of the aromatic amines and their metabolites [see pp. 207-208 in (4010)]. 

Niemenen EH, Saarinen LH, Laakso JR. 1983. Simultaneous determination of aromatic isocyanates and some carcinogenic amines in the work atmosphere by reversed-phase high-performance liquid chromatography. J Liq Chromoatogr 6(3) 453-469. 

Chester Beatty Research Institute Precautions for Laboratory Workers who Handle Carcinogenic Amines, London, 1971... 

Kralecik, P. (1996). A new TLC/AMD method for testing of textiles for carcinogenic amines arising from azo dyes. GIT Spez. Chromatogr. 16 125-129. 

---