New pathways for the rapid formation of N-nitrosamines under neutral and alkaline conditions.
Ethylene glycol, several carbohydrates (sugars) and alkanolamines influence the formation of carcinogenic N-nitrosamines in neutral and alkaline aqueous solutions at 25 degrees C in presence of dissolved nitrosyl gases. These compounds either catalyse or inhibit the reactions (depending on the experimental conditions and reagent reactivities) by forming a nitrite ester intermediate, which reacts readily with secondary amines. The reactions may explain the origin of some N-nitrosamines in vivo and in consumer products, particularly those originating from NOX pollutants. N-Nitrosamines are also formed at ambient temperatures by the gamma-radiolysis of neutral aqueous solutions of either NaNO2 or NaNO3 and secondary amines. With NaNO3, N-nitroamines are in accompanying product. These reactions are considered to proceed via N2O3 and N2O4 intermediates, generated from NaNO2 and NaNO3, respectively.
D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D007700:Kinetics; D008722:Methods; D009602:Nitrosamines / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D007202:Indicators and Reagents; D009602:Nitrosamines