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4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (Synonyms: NNK)

Katalog-Nr.GC46607

A tobacco-specific nitrosamine carcinogen

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4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone Chemische Struktur

Cas No.: 64091-91-4

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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is a tobacco-specific nitrosamine carcinogen.1 Reactive metabolites of NNK alkylate DNA, forming pyridyloxobutyl (POB) and pyridylhydroxybutyl (PHB) adducts, and induce DNA methylation. NNK (100 mg/kg, single dose) increases the protein levels of DNA methyltransferase 1 (DNMT1) in mouse bronchial epithelial cells within one day and increases hypermethylation of the tumor suppressor genes Chd13, Prdm2, and Runx3 in lung tissue within three days.2 It induces tumor formation preferentially in the lung via various routes of administration in animal models.3 NNK induces adenomas and adenocarcinomas, which are present after 16 and 50 weeks, respectively, in mouse lung when administered at a single dose of 10 µmol/animal. Lifetime administration of NNK (63.5 mg/animal) to rats results in a 90% incidence of lung tumors.4

1.Carlson, E.S., Upadhyaya, P., Villalta, P.W., et al.Analysis and identification of 2'-deoxyadenosine-derived adducts in lung and lover DNA of F-344 rats treated with the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and enantiomers of its metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanolChem. Res. Toxicol.31(5)358-370(2018) 2.Jin, H., Chen, J.X., Wang, H., et al.NNK-induced DNA methyltransferase 1 in lung tumorigenesis in A/J mice and inhibitory effects of (-)-epigallocatechin-3-gallateNutr. Cancer67(1)167-176(2016) 3.Hecht, S.S.Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosaminesChem. Res. Toxicol.11(6)559-603(1998) 4.Rivenson, A., Hoffmann, D., Prokopczyk, B., et al.Induction of lung and exocrine pancreas tumors in F344 rats by tobacco-specific and Areca-derived N-nitrosaminesCancer Res.48(23)6912-6917(1988)

Chemical Properties

Cas No. 64091-91-4 SDF
Überlieferungen NNK
Canonical SMILES O=C(CCCN(C)N=O)C1=CC=CN=C1
Formula C10H13N3O2 M.Wt 207.2
Löslichkeit DMF: 30 mg/ml, DMSO: 25 mg/ml, Ethanol: 25 mg/ml, Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 4.8263 mL 24.1313 mL 48.2625 mL
5 mM 0.9653 mL 4.8263 mL 9.6525 mL
10 mM 0.4826 mL 2.4131 mL 4.8263 mL
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