Trapping of reactive intermediates from the nitrosation of primary amines by a new type of scavenger reagent.
N-Methyl-N-nitrosoethanolamine has been used as a scavenger reagent for the in vitro detection of unstable alkylating intermediates. The nucleophilic hydroxy group of the scavenger reagent binds with electrophiles to yield chemically stable ethers, which are analysed using gas-liquid chromatography with the highly sensitive and specific chemiluminescence detector, the thermal energy analyser. In contrast to other test systems for the in vitro detection of alkylating species, non-physiological reaction conditions are avoided and direct conclusions on the structure of the reaction products can be drawn. This test system is shown to be effective for investigating the alkylating capacity of primary amines on nitrosation. From methylamine to butylamine the yield of alkylated scavenger is low, decreasing with elongation of the carbon chain. In contrast, nitrosation of aniline, benzylamine or phenylethylamine leads to much greater yields of alkylated scavenger. These compounds should therefore be included in risk assessment of endogenous nitrosation of primary amine precursors.
German Cancer Research Center, Institute for Toxicology and Chemotherapy, Heidelberg.
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Mende
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Spiegelhalder
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Wacker
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Preussmann
D000478:Alkylation; D000588:Amines; D000838:Anions; D002849:Chromatography, Gas; D004987:Ethers / Q000032:analysis; D007202:Indicators and Reagents; D008163:Luminescent Measurements; D009602:Nitrosamines
D000588:Amines; D000838:Anions; D004987:Ethers; D007202:Indicators and Reagents; D009602:Nitrosamines