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4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (CAS 64091-91-4) - chemical structure image
Molecular structure of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, CAS Number: 64091-91-4
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (CAS 64091-91-4) - chemical structure image
Molecular structure of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, CAS Number: 64091-91-4
Molecular structure of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, CAS Number: 64091-91-4

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (CAS 64091-91-4)

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Alternate Names:
NNK
Application:
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone is a nitrosamine present in smokeless tobacco that produces cancer in rats and hamsters
CAS Number:
64091-91-4
Molecular Weight:
207.23
Molecular Formula:
C10H13N3O2
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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SDS & Certificate of Analysis

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone present in the highest concentrations in smokeless tobacco out of the nitrosamines identified. Readily produces cancer in rats and hamsters. Reactive metabolites of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone have the ability to modify DNA through alkylation, resulting in the formation of pyridyloxobutyl (POB) and pyridylhydroxybutyl (PHB) adducts. These adducts can induce DNA methylation, a process where methyl groups are added to the DNA molecule. Furthermore, 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone belongs to the class of organic compounds called aryl alkyl ketones.


4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (CAS 64091-91-4) References

  1. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in human lung and liver microsomes and cytochromes P-450 expressed in hepatoma cells.  |  Smith, TJ., et al. 1992. Cancer Res. 52: 1757-63. PMID: 1312898
  2. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) by cytochrome P450IIB1 in a reconstituted system.  |  Guo, Z., et al. 1991. Carcinogenesis. 12: 2277-82. PMID: 1747927
  3. Extensive metabolic activation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers.  |  Stepanov, I., et al. 2008. Cancer Epidemiol Biomarkers Prev. 17: 1764-73. PMID: 18628430
  4. Biotransformation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in lung tissue from mouse, rat, hamster, and man.  |  Richter, E., et al. 2009. Chem Res Toxicol. 22: 1008-17. PMID: 19408892
  5. Effects of 8-methoxypsoralen on the metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in mice.  |  Feng, M., et al. 2015. Drug Metab Pharmacokinet. 30: 314-20. PMID: 26210672
  6. Contribution of Tobacco Use and 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone to Three Methyl DNA Adducts in Urine.  |  Wang, Y., et al. 2018. Chem Res Toxicol. 31: 836-838. PMID: 30136842
  7. Evaluation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) mutagenicity using in vitro and in vivo Pig-a assays.  |  Mittelstaedt, RA., et al. 2019. Mutat Res Genet Toxicol Environ Mutagen. 837: 65-72. PMID: 30595212
  8. Betel quid containing safrole enhances metabolic activation of tobacco specific 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK).  |  Tsou, HH., et al. 2019. Environ Pollut. 251: 13-21. PMID: 31071628
  9. 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone-Induced Histone Acetylation via α7nAChR-Mediated PI3K/Akt Activation and Its Impact on γ-H2AX Generation.  |  Shikata, M., et al. 2021. Chem Res Toxicol. 34: 2512-2521. PMID: 34784199
  10. 90-day nose-only inhalation toxicity study of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in Sprague-Dawley rats.  |  Hu, SC., et al. 2022. Food Chem Toxicol. 160: 112780. PMID: 34965465
  11. Determination of 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanone (NNK) arising from tobacco smoke in airborne particulate matter.  |  Aquilina, NJ., et al. 2022. Environ Int. 158: 106992. PMID: 34991253
  12. Toxicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in early development: A wide-scope metabolomics assay in zebrafish embryos.  |  Merino, C., et al. 2022. J Hazard Mater. 429: 127746. PMID: 35086039
  13. Chemopreventive effects and anti-tumorigenic mechanisms of Actinidia arguta, known as sarunashi in Japan toward 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)- induced lung tumorigenesis in a/J mouse.  |  Takata, J., et al. 2022. Genes Environ. 44: 26. PMID: 36494703
  14. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in isolated rat lung and liver.  |  Schrader, E., et al. 1998. Naunyn Schmiedebergs Arch Pharmacol. 357: 336-43. PMID: 9550307

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4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, 100 mg

sc-209854
100 mg
$364.00

We want to study the effects of NKK . So we will use NNK for cell and injection in mice. Do you have any reference that have use your in the last 10 years?

Asked by: Jorge2
Thank you for your question. Unfortunately we have no information regarding this use for our NNK biochemical, we do not have any references that discuss this use.
Answered by: Tech Service
Date published: 2021-04-16
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Rated 4 out of 5 by from Works greatSo far we have purchased twice and works as expected!
Date published: 2022-05-05
Rated 4 out of 5 by from Purchased materialI bouth this material and it work out well for us.
Date published: 2020-03-26
Rated 5 out of 5 by from Various publications cite the ability of 4Various publications cite the ability of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, a compound present in the highest concentrations in smokeless tobacco out of the nitrosamines identified, to readily produces cancer in rats and hamsters. -SCBT Publication Review
Date published: 2015-01-26
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4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone is rated 4.3 out of 5 by 3.
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