Home Aminos 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol

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

CAS No.:
76014-81-8
Catalog Number:
AG0058WH
Molecular Formula:
C10H15N3O2
Molecular Weight:
209.2450
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Purity
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Product Description
Catalog Number:
AG0058WH
Chemical Name:
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol
CAS Number:
76014-81-8
Molecular Formula:
C10H15N3O2
Molecular Weight:
209.2450
MDL Number:
MFCD00870462
IUPAC Name:
N-(4-hydroxy-4-pyridin-3-ylbutyl)-N-methylnitrous amide
InChI:
InChI=1S/C10H15N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8,10,14H,3,5,7H2,1H3
InChI Key:
OGRXKBUCZFFSTL-UHFFFAOYSA-N
SMILES:
O=NN(CCCC(c1cccnc1)O)C
Properties
Complexity:
190  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
209.116g/mol
Formal Charge:
0
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
209.249g/mol
Monoisotopic Mass:
209.116g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
65.8A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
0.7  
Literature
Title Journal
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4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism-related enzymes gene polymorphisms, NNK metabolites levels and urothelial carcinoma. Toxicology letters 20130110
The impact of Michigan's Dr Ron Davis smoke-free air law on levels of cotinine, tobacco-specific lung carcinogen and severity of self-reported respiratory symptoms among non-smoking bar employees. Tobacco control 20121101
Development, validation, and application of a liquid chromatography-tandem mass spectrometry method for the determination of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in human hair. Analytical and bioanalytical chemistry 20121101
Chemoprevention of mouse lung and colon tumors by suberoylanilide hydroxamic acid and atorvastatin. International journal of cancer 20120915
Interplay between smoking-induced genotoxicity and altered signaling in pancreatic carcinogenesis. Carcinogenesis 20120901
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In vivo and in vitro metabolism of tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), by the freshwater planarian, Dugesia japonica. Chemosphere 20120601
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Development of a method for the determination of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in urine of nonsmokers and smokers using liquid chromatography/tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis 20120407
Role of CYP2A5 in the bioactivation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in mice. The Journal of pharmacology and experimental therapeutics 20120401
Genetic variability in the metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) to 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL). International journal of cancer 20120315
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Low ratio of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol-glucuronides (NNAL-Gluc)/free NNAL increases urothelial carcinoma risk. The Science of the total environment 20110401
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Urinary excretion of the acrylonitrile metabolite 2-cyanoethylmercapturic acid is correlated with a variety of biomarkers of tobacco smoke exposure and consumption. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals 20110201
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Analysis of pyridyloxobutyl and pyridylhydroxybutyl DNA adducts in extrahepatic tissues of F344 rats treated chronically with 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and enantiomers of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol. Chemical research in toxicology 20090501
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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). Chemical research in toxicology 20080301
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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. Chemical research in toxicology 20070201
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4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol and its glucuronides in the urine of infants exposed to environmental tobacco smoke. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20060501
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Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants. Breast cancer research : BCR 20060101
Analysis of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in urine by extraction on a molecularly imprinted polymer column and liquid chromatography/atmospheric pressure ionization tandem mass spectrometry. Analytical chemistry 20051201
Relationships between cigarette consumption and biomarkers of tobacco toxin exposure. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20051201
Genotype-phenotype correlation between the polymorphic UGT2B17 gene deletion and NNAL glucuronidation activities in human liver microsomes. Pharmacogenetics and genomics 20051101
Analysis of total 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in smokers' blood. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20051101
Urinary tobacco-specific nitrosamines and 4-aminobiphenyl hemoglobin adducts measured in smokers of either regular or light cigarettes. Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20051001
Carcinogen exposure during short-term switching from regular to 'light' cigarettes. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20050601
Smokeless tobacco topography and toxin exposure. Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20050601
Urinary metabolites of a tobacco-specific lung carcinogen in nonsmoking hospitality workers. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20050501
Racial differences in exposure and glucuronidation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Cancer 20050401
Similar uptake of lung carcinogens by smokers of regular, light, and ultralight cigarettes. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20050301
Cytochrome P450 enzymes as catalysts of metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco specific carcinogen. Chemical research in toxicology 20050201
ATP-binding cassette (ABC) transporters in normal and pathological lung. Respiratory research 20050101
A comparison of urinary biomarkers of tobacco and carcinogen exposure in smokers. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20041001
Enantioselectivity of carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone by tissue fractions from human and rat and by enzymes isolated from human liver. Drug metabolism and disposition: the biological fate of chemicals 20040901
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). Carcinogenesis 20040701
Effects of cruciferous vegetable consumption on urinary metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in singapore chinese. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20040601
Identification of O2-substituted pyrimidine adducts formed in reactions of 4-(acetoxymethylnitrosamino)- 1-(3-pyridyl)-1-butanone and 4-(acetoxymethylnitros- amino)-1-(3-pyridyl)-1-butanol with DNA. Chemical research in toxicology 20040501
Carcinogen derived biomarkers: applications in studies of human exposure to secondhand tobacco smoke. Tobacco control 20040301
Children's exposure to environmental tobacco smoke: using diverse exposure metrics to document ethnic/racial differences. Environmental health perspectives 20040301
Correlation between UDP-glucuronosyltransferase genotypes and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone glucuronidation phenotype in human liver microsomes. Cancer research 20040201
Effects of reduced cigarette smoking on the uptake of a tobacco-specific lung carcinogen. Journal of the National Cancer Institute 20040121
Characterization of N-glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human liver: importance of UDP-glucuronosyltransferase 1A4. Drug metabolism and disposition: the biological fate of chemicals 20040101
Development, validation and transfer of a hydrophilic interaction liquid chromatography/tandem mass spectrometric method for the analysis of the tobacco-specific nitrosamine metabolite NNAL in human plasma at low picogram per milliliter concentrations. Rapid communications in mass spectrometry : RCM 20040101
Analysis of total 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human urine. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20031101
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. Drug metabolism and disposition: the biological fate of chemicals 20031001
Biotransformation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in peripheral human lung microsomes. Drug metabolism and disposition: the biological fate of chemicals 20030901
Synthesis of stereospecifically deuterated 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) iastereomers and metabolism by A/J mouse lung microsomes and cytochrome p450 2A5. Chemical research in toxicology 20030601
Immunomodulatory effects of the tobacco-specific carcinogen, NNK, on alveolar macrophages. Clinical and experimental immunology 20030501
Effects of benzyl isothiocyanate and 2-phenethyl isothiocyanate on benzo[a]pyrene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism in F-344 rats. Carcinogenesis 20030301
The pyridyloxobutyl DNA adduct, O6-[4-oxo-4-(3-pyridyl)butyl]guanine, is detected in tissues from 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-treated A/J mice. Chemical research in toxicology 20030101
Effect of nicotine, cotinine and phenethyl isothiocyanate on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism in the Syrian golden hamster. Toxicology 20020930
Identification of tobacco-derived compounds in human pancreatic juice. Chemical research in toxicology 20020501
Analysis of N- and O-glucuronides of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human urine. Chemical research in toxicology 20020401
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. Carcinogenesis 20020101
Quantitation of metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone after cessation of smokeless tobacco use. Cancer research 20020101
The effect of a 2-h exposure to cigarette smoke on the metabolic activation of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in A/J mice. Chemico-biological interactions 20011128
Metabolites of a tobacco-specific lung carcinogen in the urine of elementary school-aged children. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20011101
Transport of the beta -O-glucuronide conjugate of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by the multidrug resistance protein 1 (MRP1). Requirement for glutathione or a non-sulfur-containing analog. The Journal of biological chemistry 20010727
The effect of tobacco smoke, nicotine, and cotinine on the mutagenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL). Mutation research 20010725
Preparation of pyridine-N-glucuronides of tobacco-specific nitrosamines. Chemical research in toxicology 20010501
Effects of vitamins and common drugs on reduction of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in rat microsomes. Archives of physiology and biochemistry 20010401
Metabolites of a tobacco-specific lung carcinogen in nonsmoking women exposed to environmental tobacco smoke. Journal of the National Cancer Institute 20010307
Characterization of enzymes participating in carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human placenta. Chemico-biological interactions 20010130
Expression and NNK reducing activities of carbonyl reductase and 11beta-hydroxysteroid dehydrogenase type 1 in human lung. Chemico-biological interactions 20010130
Human cervical tissue metabolizes the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, via alpha-hydroxylation and carbonyl reduction pathways. Carcinogenesis 20010101
Carcinogen biomarkers for lung or oral cancer chemoprevention trials. IARC scientific publications 20010101
O-Glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1- (3-pyridyl)-1-butanol (NNAL) by human UDP-glucuronosyltransferases 2B7 and 1A9. Drug metabolism and disposition: the biological fate of chemicals 20001101
Comparative metabolism of the tobacco-related carcinogens benzo[a]pyrene, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol, and N'- nitrosonornicotine in human hepatic microsomes. Drug metabolism and disposition: the biological fate of chemicals 19970201
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