A theoretical study of N‐nitrosamine metabolites: Possible alkylating species in carcinogenesis by N,N'‐dimethyl nitrosamine

Abstract

The results of ab initio calculations using a 4-21G basis set are reported for various possible metabolites of N,N'-dimethylnitrosarnine. The relevance of these results to the nature of the alkylating agent is discussed. Although the calculations widen the range of possible alkylating agents that need to be considered, the diazonium ion appears to be the most likely candidate.

Hydrated carbonium ions as possible nitrosamine metabolites: An ab initio study

“…Whereas most of the theoretical evidence suggests that diazonium ions are the most likely alkylating agents [ 16,[18][19][20][21][22], these conclusions have been biased towards diazonium ions by the neglect of solvent.…”

“…Elsewhere, a strategy has been proposed for differentiating more clearly between the different alkylating agents as a whole [14] (and the diazohydroxide in particular [22]); these studies suggest that alkyloxonium ions should be involved in such a study.…”

“…These studies have been no more conclusive than the experimental investigations; the various conclu-*To whom correspondence should be addressed. CCC 0020-7608/87/010123-09$04.~ sions have been discussed elsewhere [22]. This shows that the problem is complex and that all the different possible alkylating agents must be thoroughly investigated [14].…”