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Chemical Compound Review:

MBNA N-butyl-N-methyl-nitrous amide

Synonyms: NMBA, CHEMBL348740, CCRIS 1122, AG-G-98820, N4007_SIGMA, ...

Lijinsky, W. et al., Suzuki, E. et al., Farrelly, J.G. et al., Gichner, T. et al., Huang, Q. et al.

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Disease relevance of N-butyl-N-methyl-nitrous amide

N-Nitromethyl-n-propylamine and N-nitrosomethyl-n-butylamine given in drinking water induced tumors of the upper gastrointestinal tract, mainly carcinomas of the esophagus, and appeared to be of comparable potency [1].

High impact information on N-butyl-N-methyl-nitrous amide

The carcinogenicity of N-nitrosomethyl-n-propylamine and five of its derivatives, including N-nitrosomethyl-n-butylamine, was compared by oral administration of the compounds to inbred F344 rats [1].
With the use of rat liver preparations, the in vitro microsomal metabolism of methylethylnitrosamine, methyl-n-butylnitrosamine, and methyl(2-phenylethyl)nitrosamine labeled with deuterium in the methyl and alpha-methylene positions has been compared with that of the parent (unlabeled) compounds [2].
Although an increased production of aldehydes was observed with the induced microsomes compared with the non-induced microsomes, no marked differences were noted between the two alkyl groups of these unsymmetric nitrosodialkylamines in regard to the extent of alpha-hydroxylation with the exception of N-nitroso-N-methylbutylamine (NMBA) [3].
Hydroxylation and dealkylation of methyl-n-butylnitrosamine and role of certain cytochrome P-450 isozymes in these reactions [4].
The organic solvents dimethylsulphoxide (DMSO), acetone, ethanol and dimethylformamide inhibited the mutagenic activity of the promutagens dimethylnitrosamine and methylbutylnitrosamine in a higher plant Arabidopsis thaliana [5].

References

Carcinogenesis in F344 rats by N-nitrosomethyl-n-propylamine derivatives. Lijinsky, W., Reuber, M.D., Saavedra, J.E., Singer, G.M. J. Natl. Cancer Inst. (1983) [Pubmed]
Relationship between carcinogenicity and in vitro metabolism of nitrosomethylethylamine, nitrosomethyl-N-butylamine, and nitrosomethyl-(2-phenylethyl)amine labeled with deuterium in the methyl and alpha-methylene positions. Farrelly, J.G., Stewart, M.L., Saavedra, J.E., Lijinsky, W. Cancer Res. (1982) [Pubmed]
Alpha-hydroxylation and mutagenicity of unsymmetrical N-nitrosodialkylamines with a butyl group. Suzuki, E., Mochizuki, M., Takeda, K., Okada, M. Jpn. J. Cancer Res. (1985) [Pubmed]
Hydroxylation and dealkylation of methyl-n-butylnitrosamine and role of certain cytochrome P-450 isozymes in these reactions. Huang, Q., Wang, S., Chen, S.C., Babcook, D.M., Park, S.S., Gelboin, H.V., Mirvish, S.S. Cancer Lett. (1993) [Pubmed]
Organic solvents inhibit the mutagenicity of promutagens dimethylnitrosamine and methylbutylnitrosamine in a higher plant Arabidopsis thaliana. Gichner, T., Velemínský, J. Mutagenesis (1986) [Pubmed]

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