A tobacco-specific nitrosamine carcinogen
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4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone

Item No. 16414

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-(methylnitrosoamino)-1-(3-pyridinyl)-1-butanone
CAS Number
64091-91-4
Synonyms
  • NNK
Molecular Formula
C10H13N3O2
Formula Weight
207.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 25 mg/mlEthanol: 25 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
229 nm
SMILES
O=C(CCCN(C)N=O)C1=CC=CN=C1
InChi Code
InChI=1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3
InChi Key
FLAQQSHRLBFIEZ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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-butanol. Chem. 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-gallate. Nutr. Cancer 67(1), 167-176 (2016).

    3. Hecht, S.S. Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines. Chem. 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-nitrosamines. Cancer Res. 48(23), 6912-6917 (1988).