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Nitroso(acetoxymethyl)methylamine

This compound is a precursor of NNK found in tobacco smoke; it exhibits immunosuppressive, mutagenic, and carcinogenic activities. In alveolar and bronchial epithelial cells, this compound inhibits production of IL-8 and MCP-1. This compound also induces the formation of tumors in vivo.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18949148

Cas No.

56856-83-8

Purity

≥98%

Formula

C4H8N2O3

Formula Wt.

132.12

Chemical Name

Acetoxymethyl methylnitrosamine

IUPAC Name

[methyl(nitroso)amino]methyl acetate

Synonym

Methyl(acetoxymethyl)nitrosamine; α-Acetoxy dimethylnitrosamine

Solubility

Soluble in water.

Appearance

Liquid

Proulx LI, Gaudreault M, Turmel V, et al. 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, a component of tobacco smoke, modulates mediator release from human bronchial and alveolar epithelial cells. Clin Exp Immunol. 2005 Apr;140(1):46-53. PMID: 15762874.

Cloutier JF, Drouin R, Castonguay A. Treatment of human cells with N-Nitroso(acetoxymethyl)methylamine: distribution patterns of piperidine-sensitive DNA damage at the nucleotide level of resolution are related to the sequence context. Chem Res Toxicol. 1999 Sep;12(9):840-9. PMID: 10490506.

Klein RG, Schmezer P, Komitowski D. Carcinogenicity of small doses of inhaled N-nitrosoacetoxymethyl-N-methylamine in Syrian golden hamsters. J Cancer Res Clin Oncol. 1986;111(2):108-9. PMID: 3700456.

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