Home Amines 76014-81-8
76014-81-8,MFCD00870462
Catalog No.:AA0058TP

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

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25mg
95%
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$287.00   $201.00
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100mg
95%
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$525.00   $368.00
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250mg
95%
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$760.00   $532.00
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0058TP
Chemical Name:
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol
CAS Number:
76014-81-8
Molecular Formula:
C10H15N3O2
Molecular Weight:
209.2450
MDL Number:
MFCD00870462
SMILES:
O=NN(CCCC(c1cccnc1)O)C
Properties
Properties
 
Form:
Solid  
Storage:
2-8℃;Inert atmosphere;  

Computed Properties
 
Complexity:
190  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
5  
Undefined Atom Stereocenter Count:
1  
XLogP3:
0.7  

Literature

Title: Stereospecific Metabolism of the Tobacco-Specific Nitrosamine, NNAL.

Journal: Chemical research in toxicology 20151116

Title: 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism-related enzymes gene polymorphisms, NNK metabolites levels and urothelial carcinoma.

Journal: Toxicology letters 20130110

Title: 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.

Journal: Tobacco control 20121101

Title: 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.

Journal: Analytical and bioanalytical chemistry 20121101

Title: Chemoprevention of mouse lung and colon tumors by suberoylanilide hydroxamic acid and atorvastatin.

Journal: International journal of cancer 20120915

Title: Interplay between smoking-induced genotoxicity and altered signaling in pancreatic carcinogenesis.

Journal: Carcinogenesis 20120901

Title: Exposure to secondhand smoke outside of a bar and a restaurant and tobacco exposure biomarkers in nonsmokers.

Journal: Environmental health perspectives 20120701

Title: In vivo and in vitro metabolism of tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), by the freshwater planarian, Dugesia japonica.

Journal: Chemosphere 20120601

Title: Smoking behavior and exposure to tobacco toxicants during 6 months of smoking progressively reduced nicotine content cigarettes.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20120501

Title: Exposure and kinetics of polycyclic aromatic hydrocarbons (PAHs) in cigarette smokers.

Journal: Chemical research in toxicology 20120416

Title: 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: Journal of pharmaceutical and biomedical analysis 20120407

Title: Role of CYP2A5 in the bioactivation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in mice.

Journal: The Journal of pharmacology and experimental therapeutics 20120401

Title: 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).

Journal: International journal of cancer 20120315

Title: Environmental tobacco smoke and children's health.

Journal: Korean journal of pediatrics 20120201

Title: European birth cohorts for environmental health research.

Journal: Environmental health perspectives 20120101

Title: 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone is correlated with 8-hydroxy-2'-deoxyguanosine in humans after exposure to environmental tobacco smoke.

Journal: The Science of the total environment 20120101

Title: Cancer chemoprevention by citrus pulp and juices containing high amounts of β-cryptoxanthin and hesperidin.

Journal: Journal of biomedicine & biotechnology 20120101

Title: Reduced exercise tolerance and pulmonary capillary recruitment with remote secondhand smoke exposure.

Journal: PloS one 20120101

Title: Estimation and correlation of cigarette smoke exposure in Canadian smokers as determined by filter analysis and biomarkers of exposure.

Journal: Regulatory toxicology and pharmacology : RTP 20111201

Title: A study to evaluate the effect on Mouth Level Exposure and biomarkers of exposure estimates of cigarette smoke exposure following a forced switch to a lower ISO tar yield cigarette.

Journal: Regulatory toxicology and pharmacology : RTP 20111201

Title: Nicotine, carbon monoxide, and carcinogen exposure after a single use of a water pipe.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20111101

Title: Urinary levels of cigarette smoke constituent metabolites are prospectively associated with lung cancer development in smokers.

Journal: Cancer research 20111101

Title: Prevention of mouse lung tumors by combinations of chemopreventive agents using concurrent and sequential administration.

Journal: Anticancer research 20111001

Title: STrengthening the Reporting of OBservational studies in Epidemiology--Molecular Epidemiology (STROBE-ME): an extension of the STROBE Statement.

Journal: PLoS medicine 20111001

Title: Metabolic study of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone to the enantiomers of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in vitro in human bronchial epithelial cells using chiral capillary electrophoresis.

Journal: Journal of chromatography. A 20110916

Title: Mainstream smoke of the waterpipe: does this environmental matrix reveal as significant source of toxic compounds?

Journal: Toxicology letters 20110910

Title: Racial differences in the relationship between number of cigarettes smoked and nicotine and carcinogen exposure.

Journal: Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20110901

Title: Urinary levels of the tobacco-specific carcinogen N'-nitrosonornicotine and its glucuronide are strongly associated with esophageal cancer risk in smokers.

Journal: Carcinogenesis 20110901

Title: The ratio of a urinary tobacco-specific lung carcinogen metabolite to cotinine is significantly higher in passive than in active smokers.

Journal: Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals 20110901

Title: The use of a novel tobacco-substitute sheet and smoke dilution to reduce toxicant yields in cigarette smoke.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110801

Title: Relationship between biomarkers of cigarette smoke exposure and biomarkers of inflammation, oxidative stress, and platelet activation in adult cigarette smokers.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20110801

Title: Facile syntheses of O(2)-[4-(3-pyridyl-4-oxobut-1-yl]thymidine, the major adduct formed by tobacco specific nitrosamine 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in vivo, and its site-specifically adducted oligodeoxynucleotides.

Journal: Chemical research in toxicology 20110620

Title: Metabolites of a tobacco-specific lung carcinogen in children exposed to secondhand or thirdhand tobacco smoke in their homes.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20110601

Title: Metabolic effects of CYP2A6 and CYP2A13 on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced gene mutation--a mammalian cell-based mutagenesis approach.

Journal: Toxicology and applied pharmacology 20110601

Title: Effect of maternal tobacco smoking or exposure to second-hand smoke on the levels of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in urine of mother and the first urine of newborn.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20110601

Title: Global surveillance of oral tobacco products: total nicotine, unionised nicotine and tobacco-specific N-nitrosamines.

Journal: Tobacco control 20110501

Title: Low ratio of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol-glucuronides (NNAL-Gluc)/free NNAL increases urothelial carcinoma risk.

Journal: The Science of the total environment 20110401

Title: Environmental tobacco smoke exposure among casino dealers.

Journal: Journal of occupational and environmental medicine 20110401

Title: Tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in smokers in the United States: NHANES 2007-2008.

Journal: Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals 20110301

Title: Is 24h nicotine equivalents a surrogate for smoke exposure based on its relationship with other biomarkers of exposure?

Journal: Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals 20110301

Title: Comparison of urine cotinine and the tobacco-specific nitrosamine metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) and their ratio to discriminate active from passive smoking.

Journal: Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20110301

Title: Urinary excretion of the acrylonitrile metabolite 2-cyanoethylmercapturic acid is correlated with a variety of biomarkers of tobacco smoke exposure and consumption.

Journal: Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals 20110201

Title: Characterization of UDP-glucuronosyltransferase 2A1 (UGT2A1) variants and their potential role in tobacco carcinogenesis.

Journal: Pharmacogenetics and genomics 20110201

Title: Nicotine metabolite ratio predicts smoking topography and carcinogen biomarker level.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20110201

Title: Microfluidic direct injection method for analysis of urinary 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) using molecularly imprinted polymers coupled on-line with LC-MS/MS.

Journal: Journal of pharmaceutical and biomedical analysis 20110125

Title: A new liquid chromatography/mass spectrometry method for 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in urine.

Journal: Rapid communications in mass spectrometry : RCM 20110115

Title: Biomarkers increase detection of active smoking and secondhand smoke exposure in critically ill patients.

Journal: Critical care medicine 20110101

Title: Effect of oral snus and medicinal nicotine in smokers on toxicant exposure and withdrawal symptoms: a feasibility study.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20110101

Title: Lysyl oxidase, a critical intra- and extra-cellular target in the lung for cigarette smoke pathogenesis.

Journal: International journal of environmental research and public health 20110101

Title: Paternal smoking and risk of childhood acute lymphoblastic leukemia: systematic review and meta-analysis.

Journal: Journal of oncology 20110101

Title: The scientific foundation for tobacco harm reduction, 2006-2011.

Journal: Harm reduction journal 20110101

Title: Urinary biomarkers for secondhand smoke.

Journal: Journal of clinical laboratory analysis 20110101

Title: Disturbances in the glutathione/ophthalmate redox buffer system in the woodchuck model of hepatitis virus-induced hepatocellular carcinoma.

Journal: HPB surgery : a world journal of hepatic, pancreatic and biliary surgery 20110101

Title: Design and study protocol of the maternal smoking cessation during pregnancy study, (M-SCOPE).

Journal: BMC public health 20110101

Title: Urine menthol as a biomarker of mentholated cigarette smoking.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20101201

Title: Urine cotinine underestimates exposure to the tobacco-derived lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in passive compared with active smokers.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20101101

Title: Urine concentrations of a tobacco-specific nitrosamine carcinogen in the U.S. population from secondhand smoke exposure.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20101101

Title: On-line concentration and determination of tobacco-specific N-nitrosamines by cation-selective exhaustive injection-sweeping-micellar electrokinetic chromatography.

Journal: Talanta 20101015

Title: Chinese 'low-tar' cigarettes do not deliver lower levels of nicotine and carcinogens.

Journal: Tobacco control 20101001

Title: Stability of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in urine samples stored at various temperatures.

Journal: Journal of analytical toxicology 20100901

Title: Temporal stability of urinary and plasma biomarkers of tobacco smoke exposure among cigarette smokers.

Journal: Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals 20100601

Title: Effect of differing levels of tobacco-specific nitrosamines in cigarette smoke on the levels of biomarkers in smokers.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20100601

Title: Formation and distribution of NNK metabolites in an isolated perfused rat lung.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100501

Title: Tobacco smoke exposure in nonsmoking hospitality workers before and after a state smoking ban.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20100401

Title: UDP-glucuronosyltransferase 1A10: activity against the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol, and a potential role for a novel UGT1A10 promoter deletion polymorphism in cancer susceptibility.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100301

Title: Adaptive regression modeling of biomarkers of potential harm in a population of U.S. adult cigarette smokers and nonsmokers.

Journal: BMC medical research methodology 20100101

Title: Associations of variants in CHRNA5/A3/B4 gene cluster with smoking behaviors in a Korean population.

Journal: PloS one 20100101

Title: Role of glutathione in the regulation of Cisplatin resistance in cancer chemotherapy.

Journal: Metal-based drugs 20100101

Title: Determination of tobacco-specific N-nitrosamines in urine of smokers and non-smokers.

Journal: Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals 20091201

Title: Elimination kinetics of the tobacco-specific biomarker and lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20091201

Title: Chinese 'herbal' cigarettes are as carcinogenic and addictive as regular cigarettes.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20091201

Title: Exposure to the carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in smokers from 3 populations with different risks of lung cancer.

Journal: International journal of cancer 20091115

Title: Population estimates for biomarkers of exposure to cigarette smoke in adult U.S. cigarette smokers.

Journal: Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20091001

Title: Longer term exposure to secondhand smoke and health outcomes in COPD: impact of urine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol.

Journal: Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20090801

Title: A comparison of exposure to carcinogens among roll-your-own and factory-made cigarette smokers.

Journal: Addiction biology 20090701

Title: Biotransformation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in lung tissue from mouse, rat, hamster, and man.

Journal: Chemical research in toxicology 20090601

Title: A modified method for the determination of tobacco specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in human urine by solid phase extraction using a molecularly imprinted polymer and liquid chromatography tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090515

Title: 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.

Journal: Chemical research in toxicology 20090501

Title: Effects of smoking cessation on eight urinary tobacco carcinogen and toxicant biomarkers.

Journal: Chemical research in toxicology 20090401

Title: Urinary levels of tobacco-specific nitrosamine metabolites in relation to lung cancer development in two prospective cohorts of cigarette smokers.

Journal: Cancer research 20090401

Title: Mitochondrial DNA adducts in the lung and liver of F344 rats chronically treated with 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and (S)-4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol.

Journal: Chemical research in toxicology 20090201

Title: A prospectively measured serum biomarker for a tobacco-specific carcinogen and lung cancer in smokers.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20090101

Title: Evidence for endogenous formation of N'-nitrosonornicotine in some long-term nicotine patch users.

Journal: Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20090101

Title: Evaluation of biomarkers of exposure and potential harm in smokers, former smokers and never-smokers.

Journal: Clinical chemistry and laboratory medicine 20090101

Title: Nicotine metabolism in three ethnic/racial groups with different risks of lung cancer.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20081201

Title: Correlation between the urine profile of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolites and N7-methylguanine in urothelial carcinoma patients.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20081201

Title: Smokers with the CHRNA lung cancer-associated variants are exposed to higher levels of nicotine equivalents and a carcinogenic tobacco-specific nitrosamine.

Journal: Cancer research 20081115

Title: Subpicogram per milliliter determination of the tobacco-specific carcinogen metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in human urine using liquid chromatography-tandem mass spectrometry.

Journal: Analytical chemistry 20081101

Title: Surveillance of moist snuff: total nicotine, moisture, pH, un-ionized nicotine, and tobacco-specific nitrosamines.

Journal: Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20081101

Title: [Study advances on carcinogens and their metabolites in urine of smokers].

Journal: Wei sheng yan jiu = Journal of hygiene research 20081101

Title: Effect of COPD treatments on MRP1-mediated transport in bronchial epithelial cells.

Journal: International journal of chronic obstructive pulmonary disease 20080901

Title: Quantitation of pyridylhydroxybutyl-DNA adducts in liver and lung of F-344 rats treated with 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and enantiomers of its metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol.

Journal: Chemical research in toxicology 20080701

Title: Extensive metabolic activation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20080701

Title: A 12-month, randomized, controlled study to evaluate exposure and cardiovascular risk factors in adult smokers switching from conventional cigarettes to a second-generation electrically heated cigarette smoking system.

Journal: Journal of clinical pharmacology 20080501

Title: Exposure to nicotine and a tobacco-specific carcinogen increase with duration of use of smokeless tobacco.

Journal: Tobacco control 20080401

Title: Detection and quantitation of N'-nitrosonornicotine in human toenails by liquid chromatography-electrospray ionization-tandem mass spectrometry.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20080401

Title: 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).

Journal: Chemical research in toxicology 20080301

Title: Smoking reduction fails to improve clinical and biological markers of cardiac disease: a randomized controlled trial.

Journal: Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20080301

Title: Metabolism of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone to its biomarker total NNAL in smokeless tobacco users.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20080301

Title: Biotransformation and transport of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in bile duct-cannulated wild-type and Mrp2/Abcc2-deficient (TR ) Wistar rats.

Journal: Carcinogenesis 20071201

Title: Analysis of CYP2A contributions to metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in human peripheral lung microsomes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20071101

Title: Nicotine and carcinogen exposure with smoking of progressively reduced nicotine content cigarette.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20071101

Title: The association of a tobacco-specific biomarker and cigarette consumption and its dependence on host characteristics.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20070901

Title: Determination of the role of target tissue metabolism in lung carcinogenesis using conditional cytochrome P450 reductase-null mice.

Journal: Cancer research 20070815

Title: Similar exposure to a tobacco-specific carcinogen in smokeless tobacco users and cigarette smokers.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20070801

Title: Relationship of human toenail nicotine, cotinine, and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol to levels of these biomarkers in plasma and urine.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20070701

Title: Urinary biomarkers to assess exposure of cats to environmental tobacco smoke.

Journal: American journal of veterinary research 20070401

Title: The UDP-glucuronosyltransferase 2B17 gene deletion polymorphism: sex-specific association with urinary 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronidation phenotype and risk for lung cancer.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20070401

Title: An association of CYP2A6 genotype and smoking topography.

Journal: Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20070401

Title: Smokeless tobacco brand switching: a means to reduce toxicant exposure?

Journal: Drug and alcohol dependence 20070316

Title: Relationship between machine-derived smoke yields and biomarkers in cigarette smokers in Germany.

Journal: Regulatory toxicology and pharmacology : RTP 20070301

Title: 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.

Journal: Chemical research in toxicology 20070201

Title: Effects of high dose transdermal nicotine replacement in cigarette smokers.

Journal: Pharmacology, biochemistry, and behavior 20070101

Title: Reduced inflammatory response in cigarette smoke exposed Mrp1/Mdr1a/1b deficient mice.

Journal: Respiratory research 20070101

Title: Meat, vegetables and genetic polymorphisms and the risk of colorectal carcinomas and adenomas.

Journal: BMC cancer 20070101

Title: Determination of tobacco specific hemoglobin adducts in smoking mothers and new born babies by mass spectrometry.

Journal: Biomarker insights 20070101

Title: A comparison of nicotine dose estimates in smokers between filter analysis, salivary cotinine, and urinary excretion of nicotine metabolites.

Journal: Psychopharmacology 20061201

Title: Study of the metabolism on tobacco-specific N-nitrosamines in the rabbit by solid-phase extraction and liquid chromatography-tandem mass spectrometry.

Journal: Analytical and bioanalytical chemistry 20061201

Title: Toxicant exposure in cigarette reducers versus light smokers.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20061201

Title: Mass spectrometric quantitation of nicotine, cotinine, and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in human toenails.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20061201

Title: A biomarker of exposure to environmental tobacco smoke (ETS) and Ernst Wynder's opinion about ETS and lung cancer.

Journal: Preventive medicine 20061001

Title: Combined analysis of r-1,t-2,3,c-4-tetrahydroxy-1,2,3,4-tetrahydrophenanthrene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in smokers' plasma.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20060801

Title: [Detection of metabolites of tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in lung cancer smokers' urine].

Journal: Zhongguo fei ai za zhi = Chinese journal of lung cancer 20060620

Title: Determination of tobacco-specific N-nitrosamines in rabbit serum by capillary zone electrophoresis and capillary electrophoresis-electrospray ionization-mass spectrometry with solid-phase extraction.

Journal: Electrophoresis 20060601

Title: Prevention of mouse lung tumors by targretin.

Journal: International journal of cancer 20060501

Title: 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol and its glucuronides in the urine of infants exposed to environmental tobacco smoke.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20060501

Title: Uptake of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by Moldovan children.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20060101

Title: Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants.

Journal: Breast cancer research : BCR 20060101

Title: 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.

Journal: Analytical chemistry 20051201

Title: Relationships between cigarette consumption and biomarkers of tobacco toxin exposure.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20051201

Title: Genotype-phenotype correlation between the polymorphic UGT2B17 gene deletion and NNAL glucuronidation activities in human liver microsomes.

Journal: Pharmacogenetics and genomics 20051101

Title: Analysis of total 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in smokers' blood.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20051101

Title: Urinary tobacco-specific nitrosamines and 4-aminobiphenyl hemoglobin adducts measured in smokers of either regular or light cigarettes.

Journal: Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20051001

Title: Carcinogen exposure during short-term switching from regular to 'light' cigarettes.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20050601

Title: Smokeless tobacco topography and toxin exposure.

Journal: Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20050601

Title: Urinary metabolites of a tobacco-specific lung carcinogen in nonsmoking hospitality workers.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20050501

Title: Racial differences in exposure and glucuronidation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK).

Journal: Cancer 20050401

Title: Similar uptake of lung carcinogens by smokers of regular, light, and ultralight cigarettes.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20050301

Title: Cytochrome P450 enzymes as catalysts of metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco specific carcinogen.

Journal: Chemical research in toxicology 20050201

Title: ATP-binding cassette (ABC) transporters in normal and pathological lung.

Journal: Respiratory research 20050101

Title: A comparison of urinary biomarkers of tobacco and carcinogen exposure in smokers.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20041001

Title: 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.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20040901

Title: 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).

Journal: Carcinogenesis 20040701

Title: Effects of cruciferous vegetable consumption on urinary metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in singapore chinese.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20040601

Title: 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.

Journal: Chemical research in toxicology 20040501

Title: Carcinogen derived biomarkers: applications in studies of human exposure to secondhand tobacco smoke.

Journal: Tobacco control 20040301

Title: Children's exposure to environmental tobacco smoke: using diverse exposure metrics to document ethnic/racial differences.

Journal: Environmental health perspectives 20040301

Title: Correlation between UDP-glucuronosyltransferase genotypes and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone glucuronidation phenotype in human liver microsomes.

Journal: Cancer research 20040201

Title: Effects of reduced cigarette smoking on the uptake of a tobacco-specific lung carcinogen.

Journal: Journal of the National Cancer Institute 20040121

Title: Characterization of N-glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human liver: importance of UDP-glucuronosyltransferase 1A4.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20040101

Title: 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.

Journal: Rapid communications in mass spectrometry : RCM 20040101

Title: Analysis of total 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human urine.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20031101

Title: 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.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20031001

Title: Biotransformation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in peripheral human lung microsomes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20030901

Title: 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.

Journal: Chemical research in toxicology 20030601

Title: Immunomodulatory effects of the tobacco-specific carcinogen, NNK, on alveolar macrophages.

Journal: Clinical and experimental immunology 20030501

Title: 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.

Journal: Carcinogenesis 20030301

Title: 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.

Journal: Chemical research in toxicology 20030101

Title: Effect of nicotine, cotinine and phenethyl isothiocyanate on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism in the Syrian golden hamster.

Journal: Toxicology 20020930

Title: Identification of tobacco-derived compounds in human pancreatic juice.

Journal: Chemical research in toxicology 20020501

Title: Analysis of N- and O-glucuronides of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human urine.

Journal: Chemical research in toxicology 20020401

Title: 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.

Journal: Carcinogenesis 20020101

Title: Quantitation of metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone after cessation of smokeless tobacco use.

Journal: Cancer research 20020101

Title: 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.

Journal: Chemico-biological interactions 20011128

Title: Metabolites of a tobacco-specific lung carcinogen in the urine of elementary school-aged children.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20011101

Title: 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.

Journal: The Journal of biological chemistry 20010727

Title: The effect of tobacco smoke, nicotine, and cotinine on the mutagenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL).

Journal: Mutation research 20010725

Title: Preparation of pyridine-N-glucuronides of tobacco-specific nitrosamines.

Journal: Chemical research in toxicology 20010501

Title: Effects of vitamins and common drugs on reduction of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in rat microsomes.

Journal: Archives of physiology and biochemistry 20010401

Title: Metabolites of a tobacco-specific lung carcinogen in nonsmoking women exposed to environmental tobacco smoke.

Journal: Journal of the National Cancer Institute 20010307

Title: Characterization of enzymes participating in carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human placenta.

Journal: Chemico-biological interactions 20010130

Title: Expression and NNK reducing activities of carbonyl reductase and 11beta-hydroxysteroid dehydrogenase type 1 in human lung.

Journal: Chemico-biological interactions 20010130

Title: Human cervical tissue metabolizes the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, via alpha-hydroxylation and carbonyl reduction pathways.

Journal: Carcinogenesis 20010101

Title: Carcinogen biomarkers for lung or oral cancer chemoprevention trials.

Journal: IARC scientific publications 20010101

Title: O-Glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1- (3-pyridyl)-1-butanol (NNAL) by human UDP-glucuronosyltransferases 2B7 and 1A9.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20001101

Title: 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.

Journal: Drug metabolism and disposition: the biological fate of chemicals 19970201

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Tags:76014-81-8 Molecular Formula|76014-81-8 MDL|76014-81-8 SMILES|76014-81-8 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol