Date published: 2025-11-22

1-800-457-3801

SCBT Portrait Logo
Seach Input

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol (CAS 76014-81-8)

0.0(0)
Write a reviewAsk a question

Alternate Names:
α-[3-(Methylnitrosoamino)propyl]-3-pyridinemethanol; 4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl)butan-1-ol; rac NNAL
Application:
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol is a tobacco-specific nitrosamine NNK metabolite
CAS Number:
76014-81-8
Molecular Weight:
209.25
Molecular Formula:
C10H15N3O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

QUICK LINKS

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol, scientifically known as NNK, is a tobacco-specific nitrosamine belonging to the nitrosamine family. 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol is primarily formed during the combustion of tobacco products, resulting in its presence in the smoke. 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol plays a role in scientific investigations due to its carcinogenic properties. Researchers utilize 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol to explore the impact of tobacco smoke on human cells and tissues, as well as to delve into the mechanisms underlying carcinogenesis. Furthermore, 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol serves as useful in studying the effects of tobacco smoke on the immune system. Operating as a potent carcinogen, 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol exerts its influence by binding to DNA and inducing mutations. Metabolized by cytochrome P450 enzymes, it undergoes conversion into its active form, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK-N-oxide). Subsequently, NNK-N-oxide binds to DNA, leading to mutations that can initiate cancer development. This characteristic makes 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol a significant subject of research and investigation.


4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol (CAS 76014-81-8) References

  1. O-Glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1- (3-pyridyl)-1-butanol (NNAL) by human UDP-glucuronosyltransferases 2B7 and 1A9.  |  Ren, Q., et al. 2000. Drug Metab Dispos. 28: 1352-60. PMID: 11038164
  2. Analysis of N- and O-glucuronides of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human urine.  |  Carmella, SG., et al. 2002. Chem Res Toxicol. 15: 545-50. PMID: 11952341
  3. Comparative metabolism of the tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol by rat cytochrome P450 2A3 and human cytochrome P450 2A13.  |  Jalas, JR., et al. 2003. Drug Metab Dispos. 31: 1199-202. PMID: 12975327
  4. Analysis of total 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human urine.  |  Carmella, SG., et al. 2003. Cancer Epidemiol Biomarkers Prev. 12: 1257-61. PMID: 14652291
  5. Analysis of total 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in smokers' blood.  |  Carmella, SG., et al. 2005. Cancer Epidemiol Biomarkers Prev. 14: 2669-72. PMID: 16284395
  6. 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol and its glucuronides in the urine of infants exposed to environmental tobacco smoke.  |  Hecht, SS., et al. 2006. Cancer Epidemiol Biomarkers Prev. 15: 988-92. PMID: 16702381
  7. Mass spectrometric quantitation of nicotine, cotinine, and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in human toenails.  |  Stepanov, I., et al. 2006. Cancer Epidemiol Biomarkers Prev. 15: 2378-83. PMID: 17164359
  8. 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
  9. Formation and accumulation of pyridyloxobutyl DNA adducts in F344 rats chronically treated with 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and enantiomers of its metabolite, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol.  |  Lao, Y., et al. 2007. Chem Res Toxicol. 20: 235-45. PMID: 17305407
  10. Formation of formaldehyde adducts in the reactions of DNA and deoxyribonucleosides with alpha-acetates of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL), and N-nitrosodimethylamine (NDMA).  |  Cheng, G., et al. 2008. Chem Res Toxicol. 21: 746-51. PMID: 18205321
  11. Elimination kinetics of the tobacco-specific biomarker and lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol.  |  Goniewicz, ML., et al. 2009. Cancer Epidemiol Biomarkers Prev. 18: 3421-5. PMID: 19959691
  12. 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
  13. Absolute configuration of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol formed metabolically from 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone.  |  Hecht, SS., et al. 1997. Carcinogenesis. 18: 1851-4. PMID: 9328186

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol, 10 mg

sc-214216
10 mg
$340.00

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol, 50 mg

sc-214216A
50 mg
$505.00

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

sc-214216B
100 mg
$872.00

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol, 1 g

sc-214216C
1 g
$4248.00