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4-(Methylnitrosamino)-1-(3-pyridyl-N-oxide)-1-butanol (CAS 85352-99-4)

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Alternate Names:
NNAL-N-Oxide
CAS Number:
85352-99-4
Molecular Weight:
225.24
Molecular Formula:
C10H15N3O3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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4-(Methylnitrosamino)-1-(3-pyridyl-N-oxide)-1-butanol is a metabolite of NNK, which is a tobacco-specific nitrosamine.


4-(Methylnitrosamino)-1-(3-pyridyl-N-oxide)-1-butanol (CAS 85352-99-4) References

  1. Tumorigenicity and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol enantiomers and metabolites in the A/J mouse.  |  Upadhyaya, P., et al. 1999. Carcinogenesis. 20: 1577-82. PMID: 10426810
  2. Disposition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in bile duct-cannulated rats: stereoselective metabolism and tissue distribution.  |  Wu, Z., et al. 2002. Carcinogenesis. 23: 171-9. PMID: 11756238
  3. Stereoselective metabolism and tissue retention in rats of the individual enantiomers of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL), metabolites of the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK).  |  Zimmerman, CL., et al. 2004. Carcinogenesis. 25: 1237-42. PMID: 14988218
  4. Investigation of the reaction of myosmine with sodium nitrite in vitro and in rats.  |  Hecht, SS., et al. 2007. Chem Res Toxicol. 20: 543-9. PMID: 17291014
  5. Synthesis of 4-[2-aminoethyl(nitrosamino)]-1-pyridin-3-yl-butan-1-one, a new NNK hapten for the induction of N-nitrosamine-specific antibodies.  |  Prodhomme, EJ., et al. 2007. Bioconjug Chem. 18: 2045-53. PMID: 17939731
  6. 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
  7. 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
  8. Metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in the patas monkey: pharmacokinetics and characterization of glucuronide metabolites.  |  Hecht, SS., et al. 1993. Carcinogenesis. 14: 229-36. PMID: 8435864
  9. Simultaneous solid-phase extraction and gas chromatographic-mass spectrometric determination of hemoglobin adducts from tobacco-specific nitrosamines and aromatic amines.  |  Kutzer, C., et al. 1997. J Chromatogr Sci. 35: 1-6. PMID: 8989869
  10. 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

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

4-(Methylnitrosamino)-1-(3-pyridyl-N-oxide)-1-butanol, 5 mg

sc-206777
5 mg
$330.00