The Action of Nitrous Acid Upon Creatinine and Some of Its Derivatives

Abstract

The work discussed in the present paper is an attempt to determine the reactivity of nitrous acid with creatinine and several of its derivatives and to consider the significance of the results for the formulation of the constitution of these substances.

Creatinine: a food component that is nitrosated-denitrosated to yield methylurea

“…CRN is known to be nitrosated to give CRN 5-oxime and 1 -methylhydantoin 5-oxime (Figure 3) (Greenwald and Levy, 1948;Archer et al, 1971), and these could be intermediates in the production of MU. Accordingly, we nitrosated samples of these oximes and also of CRN, this time using only 100 mM nitrite.…”

The Chemistry Of The Glycocyamidines

“…The behavior of glycocyamidine is analogous to that of creatinine (137). The behavior of V2,3-dimethylcreatinine is interesting; although all its nitrogen atoms are blocked by methylation, it nevertheless evolves nitrogen with nitrous acid quite rapidly.…”

“…The same benzoylcreatinine may be obtained by similar treatment from creatine (303). Later a product obtained from creatinine by treatment with benzoyl chloride was thought erroneously to be an isomer of the benzoylcreatinine already known ( 129), but finally it proved to be either a mixture of mono-and tribenzoylcreatinines (168) or another crystalline modification of benzoylcreatinine (137). By using benzoyl chloride in great excess, tribenzoylcreatinine (CV) could be obtained in pure form (129); it is considered to be a derivative of the enolic form of creatinine (129).…”

“…On treating creatinine in acetic acid solution with nitrous acid, one atom of nitrogen is split off; this reaction is hindered by mineral acids (137,236,319). Therefore, by performing the reaction in 23 per cent nitric acid both "1-methylhydantoin oxime" (CXXXII) and some "creatinine oxime" (CXXXIII) are obtained from creatinine (268).…”

“…W2-Acetyl-and W2-benzoylcreatinines, containing neither a free amino nor a free imino group, evolve nitrogen with nitrous acid only very slowly; this can be explained by assuming slow hydrolysis of the acyl group (137). With nitrous acid JV2-benzoylcreatinine furnishes an oxime (CXXXIX) (137).…”