Ester hydrolysis and nitrosative deamination of novocaine in aqueous solutions.

In aqueous solutions, the kinetic features of both the hydrolysis reaction of the ester function of novocaine in alkaline medium and the nitrosation reaction of the primary amine group of novocaine in mild acid medium were investigated by UV/vis spectroscopy. The ester hydrolysis shows first-order kinetics with respect to both the drug and the nucleophile, OH-, concentrations, thus following a typical S(N)2 (Ac) mechanism. The rate of the reaction decreases strongly with the polarity of the reaction media, analyzed for both dioxane-water and Me2SO-water mixtures.