Studies on the Formation of Nitrosamines (III)

The Reaction Products of Glycocyamine and Sodium Nitrite

Abstract

The reaction products of glycocyamine, one of the naturally occurring guanidines, and nitrite under acidic conditions were explored. The main product was identified as carboxymethylnitrosourea, a derivative of hydantoic acid whose secondary amino group was nitrosated, by elemental analysis and NMR spectrum. The structure was further confirmed by mixed analysis and by comparing IR and absorption spectra with the reaction product of hydantoic acid and nitrite.
A nitrosocyanamide was expected to be one of the reaction products, but it could not be detected in various conditions examined. Stability and the decomposition products of carboxymethylnitrosourea were also discussed.