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N-076 Cerilliant

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) solution

1.0 mg/mL in methanol, ampule of 1 mL, certified reference material

Synonym: 4-(Methylnitrosamino)-1-(3-pyridinyl)-1-butanone, 4-(Methylnitrosoamino)-1-(3-pyridinyl)-1-butanone, NNK

  • CAS Number 64091-91-4

  • Empirical Formula (Hill Notation) C10H13N3O2

  • Molecular Weight 207.23

  •  MDL number MFCD00274580

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Properties

Related Categories Analytical Standards, Analytical/Chromatography, Certified Reference Materials (CRMs), Certified Reference Materials from Cerilliant, Stimulants (non-amphetamine) More...
grade   certified reference material
feature   Snap-N-Spike®/Snap-N-Shoot®
packaging   ampule of 1 mL
concentration   1.0 mg/mL in methanol
storage temp.   −20°C

Description

General description

A Certified Spiking Solution® suitable for use in nicotine testing, environmental monitoring, or clinical and diagnostic testing of nicotine biomarkers by LC-MS/MS or GC/MS. Also known as nicotine-derived nitrosamine ketone, NNK is a potent carcinogen and biomarker of exposure to cigarette smoke. NNK, produced upon the curing of tobacco, is found in a variety of tobacco products including chewing tobacco, snuff, cigarettes, and cigars.

Legal Information

CERTIFIED SPIKING SOLUTIONS is a registered trademark of Cerilliant Corporation

Snap-N-Shoot is a registered trademark of Cerilliant Corporation

Snap-N-Spike is a registered trademark of Cerilliant Corporation

Price and Availability

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
F,T
Risk Statements (Europe) 
Safety Statements (Europe) 
16-36/37-45
WGK Germany 
1
Flash Point(F) 
48.2 °F
Flash Point(C) 
9 °C

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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Nicotine and gastrointestinal disorders: its role in ulceration and cancer development. Chu KM, Cho CH, and Shin VY Curr. Pharm. Des. 19(1), 5-10, (2013)

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Alteration of serum miR-206 and miR-133b is associated with lung carcinogenesis induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Wu J, Yang T, Li X, et al. Toxicol. Appl. Pharmacol. 267(3), 238-46, (2013)

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Formation and repair of pyridyloxobutyl DNA adducts and their relationship to tumor yield in A/J mice. Urban AM, Upadhyaya P, Cao Q, et al. Chem. Res. Toxicol. 25(10), 2167-78, (2012)

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Prevention of tobacco carcinogen-induced lung cancer in female mice using antiestrogens. Stabile LP, Rothstein ME, Cunningham DE, et al. Carcinogenesis 33(11), 2181-9, (2012)

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The tobacco carcinogen nitrosamine induces a differential gene expression response in tumour susceptible A/J and resistant C3H mouse lungs. Gordon W, Galitovskiy V, Edwards R, et al. Eur. J. Cancer 49(3), 725-33, (2013)

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Tobacco carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone initiates and enhances pancreatitis responses. Alexandre M, Uduman AK, Minervini S, et al. Am. J. Physiol. Gastrointest. Liver Physiol. 303(6), G696-704, (2012)

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Chemoprevention by N-acetylcysteine of low-dose CT-induced murine lung tumorigenesis. Miller MS, Moore JE, Walb MC, et al. Carcinogenesis 34(2), 319-24, (2013)

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Comparison of genotoxicant-modified transcriptomic responses in conventional and epigenetically stabilized primary rat hepatocytes with in vivo rat liver data. Doktorova TY, Ellinger-Ziegelbauer H, Vinken M, et al. Arch. Toxicol. 86(11), 1703-15, (2012)

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Carcinogenicity and DNA adduct formation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and enantiomers of its metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in F-344 rats. Balbo S, Johnson CS, Kovi RC, et al. Carcinogenesis 35(12), 2798-806, (2014)

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The impact of water pipe and tobacco marketing on young people. Printz C Cancer 120(19), 2941, (2014)

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Royal sun medicinal mushroom Agaricus brasiliensis (higher Basidiomycetes) and the attenuation of pulmonary inflammation induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Croccia C, Lopes AJ, Pinto LF, et al. Int. J. Med. Mushrooms 15(4), 345-55, (2013)

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A simple identification of novel carbonyl reducing enzymes in the metabolism of the tobacco specific carcinogen NNK. Skarydova L, Zverinova M, Stambergova H, et al. Drug Metab. Lett. 6(3), 174-81, (2012)

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Metabolism of nicotine and 4-(methylnitrosamino)-l-(3-pyridyl)-lbutanone (NNK) in menthol and non-menthol cigarette smokers. Sarkar M, Wang J, and Liang Q Drug Metab. Lett. 6(3), 198-206, (2012)

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Apigenin inhibits NNK-induced focal adhesion kinase activation in pancreatic cancer cells. Pham H, Chen M, Takahashi H, et al. Pancreas 41(8), 1306-15, (2012)

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Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone binding and access channel in human cytochrome P450 2A6 and 2A13 enzymes. DeVore NM and Scott EE J. Biol. Chem. 287(32), 26576-85, (2012)

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Chemoprevention of lung tumorigenesis by intranasally administered diindolylmethane in A/J mice. Qian X, Song JM, Melkamu T, et al. Carcinogenesis 34(4), 841-9, (2013)

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Simultaneous determination of NNK and its seven metabolites in rabbit blood by hydrophilic interaction liquid chromatography-tandem mass spectrometry. Lang H, Wang S, Zhang Q, et al. Anal. Bioanal. Chem 405(6), 2083-9, (2013)

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4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism-related enzymes gene polymorphisms, NNK metabolites levels and urothelial carcinoma. Chung CJ, Pu YS, Shiue HS, et al. Toxicol. Lett. 216(1), 16-22, (2013)

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Mesenchymal and stem-like cell properties targeted in suppression of chronically-induced breast cell carcinogenesis. Rathore K and Wang HC Cancer Lett. 333(1), 113-23, (2013)

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Kinetics of O(6)-pyridyloxobutyl-2'-deoxyguanosine repair by human O(6)-alkylguanine DNA alkyltransferase. Kotandeniya D, Murphy D, Yan S, et al. Biochemistry 52(23), 4075-88, (2013)

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Joint effect of arsenic methylation profile and NNK metabolites on urothelial carcinoma. Wu CC, Su CT, Lee HL, et al. J. Urol. 188(5), 1701-5, (2012)

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The application of hepatic P450 reductase null gpt delta mice in studying the role of hepatic P450 in genotoxic carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced mutagenesis. Luan Y, Xing G, Qi X, et al. Arch. Toxicol. 86(11), 1753-61, (2012)

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4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) regulates CTL activation and memory programming. Sun Z and Xiao Z Biochem. Biophys. Res. Commun. 435(3), 472-6, (2013)

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Tobacco-specific N-nitrosamine exposures and cancer risk in the Shanghai Cohort Study: remarkable coherence with rat tumor sites. Stepanov I, Sebero E, Wang R, et al. Int. J. Cancer 134(10), 2278-83, (2014)

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Deficiency of CCAAT/enhancer binding protein family DNA binding prevents malignant conversion of adenoma to carcinoma in NNK-induced lung carcinogenesis in the mouse. Kimura S, Paiz J, Yoneda M, et al. Mol. Cancer 11, 90, (2012)

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Proteomic analysis of differentially expressed proteins in lung cancer in Wistar rats using NNK as an inducer. Chaudhary N, Bhatnagar S, Malik S, et al. Chem. Biol. Interact. 204(2), 125-34, (2013)

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Achaete-scute complex homolog-1 promotes DNA repair in the lung carcinogenesis through matrix metalloproteinase-7 and O(6)-methylguanine-DNA methyltransferase. Wang XY, Jensen-Taubman SM, Keefe KM, et al. PLoS ONE 7(12), e52832, (2012)

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4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone induces retinoic acid receptor β hypermethylation through DNA methyltransferase 1 accumulation in esophageal squamous epithelial cells. Wang J, Zhao SL, Li Y, et al. Asian Pac. J. Cancer Prev. 13(5), 2207-12, (2012)

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Suppressive oligodeoxynucleotides reduce lung cancer susceptibility in mice with silicosis. Bode C, Kinjo T, Alvord WG, et al. Carcinogenesis 35(5), 1078-83, (2014)

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Chronic exposure of lung alveolar epithelial type II cells to tobacco-specific carcinogen NNK results in malignant transformation: a new in vitro lung carcinogenesis model. Mennecier G, Torres LN, Cogliati B, et al. Mol. Carcinog. 53(5), 392-402, (2014)

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