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Home > Nitro Compounds > 80508-23-2
80508-23-2 | 3-(1-nitrosopyrrolidin-2-yl)pyridine
CAS No: 80508-23-2 Catalog No: AG0052J2 MDL No:
Product Description
Catalog Number:
AG0052J2
Chemical Name:
3-(1-nitrosopyrrolidin-2-yl)pyridine
CAS Number:
80508-23-2
Molecular Formula:
C9H11N3O
Molecular Weight:
177.2031
IUPAC Name:
3-(1-nitrosopyrrolidin-2-yl)pyridine
InChI:
InChI=1S/C9H11N3O/c13-11-12-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,9H,2,4,6H2
InChI Key:
XKABJYQDMJTNGQ-UHFFFAOYSA-N
SMILES:
O=NN1CCCC1c1cccnc1
UN Number:
2810
Properties
Complexity:
186
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
177.09g/mol
Formal Charge:
0
Heavy Atom Count:
13
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
177.207g/mol
Monoisotopic Mass:
177.09g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
45.6A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
1.1
Literature
| Title | Journal |
|---|---|
| In vitro metabolism of N'-Nitrosonornicotine catalyzed by cytochrome P450 2A13 and its inhibition by nicotine, N'-Nitrosoanatabine and N'-Nitrosoanabasine. | Chemico-biological interactions 20161225 |
| In vitro exposure of tobacco specific nitrosamines decreases the rat lung phospholipids by enhanced phospholipase A2 activity. | Toxicology in vitro : an international journal published in association with BIBRA 20140901 |
| Analysis of N'-nitrosonornicotine and its metabolites in rabbit blood with liquid chromatography/tandem mass spectrometric method. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120615 |
| Major tobacco companies have technology to reduce carcinogen levels but do not apply it to popular smokeless tobacco products. | Tobacco control 20111101 |
| Urinary levels of the tobacco-specific carcinogen N'-nitrosonornicotine and its glucuronide are strongly associated with esophageal cancer risk in smokers. | Carcinogenesis 20110901 |
| Environmental mutagens may be implicated in the emergence of drug-resistant microorganisms. | FEMS microbiology letters 20110401 |
| Enhanced phospholipase B activity and alteration of phospholipids and neutral lipids in Saccharomyces cerevisiae exposed to N-nitrosonornicotine. | Antonie van Leeuwenhoek 20110301 |
| Three nicotine demethylase genes mediate nornicotine biosynthesis in Nicotiana tabacum L.: functional characterization of the CYP82E10 gene. | Phytochemistry 20101201 |
| Adsorption of nitrosamines by mesoporous zeolite. | Journal of colloid and interface science 20100815 |
| [Determination of four carcinogens in mainstream cigarette smoke by liquid chromatography-tandem mass spectrometry]. | Se pu = Chinese journal of chromatography 20100801 |
| Determination of tobacco-specific N-nitrosamines in urine of smokers and non-smokers. | Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals 20091201 |
| Incremental lifetime cancer risks computed for benzo[a]pyrene and two tobacco-specific N-nitrosamines in mainstream cigarette smoke compared with lung cancer risks derived from epidemiologic data. | Regulatory toxicology and pharmacology : RTP 20091101 |
| Presence of the carcinogen N'-nitrosonornicotine in the urine of some users of oral nicotine replacement therapy products. | Cancer research 20091101 |
| The influence of repair pathways on the cytotoxicity and mutagenicity induced by the pyridyloxobutylation pathway of tobacco-specific nitrosamines. | Chemical research in toxicology 20090817 |
| Quantitation of pyridyloxobutyl DNA adducts in nasal and oral mucosa of rats treated chronically with enantiomers of N'-nitrosonornicotine. | Chemical research in toxicology 20090501 |
| Effect of CYP2A13 active site mutation N297A on metabolism of coumarin and tobacco-specific nitrosamines. | Drug metabolism and disposition: the biological fate of chemicals 20090301 |
| Evaluation of the mutagenic effects of myosmine in human lymphocytes using the HPRT gene mutation assay. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20090101 |
| Evidence for endogenous formation of N'-nitrosonornicotine in some long-term nicotine patch users. | Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20090101 |
| CYP2A6 polymorphisms and risk for tobacco-related cancers. | Pharmacogenomics 20081101 |
| Mouse model of diethylnitrosamine-induced gastric cancer. | The Journal of surgical research 20080801 |
| Glucuronidation of tobacco-specific nitrosamines by UGT2B10. | Drug metabolism and disposition: the biological fate of chemicals 20080501 |
| RNA interference (RNAi)-induced suppression of nicotine demethylase activity reduces levels of a key carcinogen in cured tobacco leaves. | Plant biotechnology journal 20080501 |
| A susceptibility locus for lung cancer maps to nicotinic acetylcholine receptor subunit genes on 15q25. | Nature 20080403 |
| Detection and quantitation of N'-nitrosonornicotine in human toenails by liquid chromatography-electrospray ionization-tandem mass spectrometry. | Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20080401 |
| Basic and clinical aspects of non-neuronal acetylcholine: biological and clinical significance of non-canonical ligands of epithelial nicotinic acetylcholine receptors. | Journal of pharmacological sciences 20080201 |
| Functional characterization of CYP2A13 polymorphisms. | Xenobiotica; the fate of foreign compounds in biological systems 20071201 |
| Endogenous formation of N'-nitrosonornicotine in F344 rats in the presence of some antioxidants and grape seed extract. | Journal of agricultural and food chemistry 20070822 |
| SLURP-1 and -2 in normal, immortalized and malignant oral keratinocytes. | Life sciences 20070530 |
| Nitrosamines as nicotinic receptor ligands. | Life sciences 20070530 |
| A new method for estimating the retention of selected smoke constituents in the respiratory tract of smokers during cigarette smoking. | Inhalation toxicology 20070201 |
| Analysis of pyridyloxobutyl DNA adducts in F344 rats chronically treated with (R)- and (S)-N'-nitrosonornicotine. | Chemical research in toxicology 20070201 |
| Development of a commercial cigarette 'market map' comparison methodology for evaluating new or non-conventional cigarettes. | Regulatory toxicology and pharmacology : RTP 20061201 |
| The nicotinic receptor antagonists abolish pathobiologic effects of tobacco-derived nitrosamines on BEP2D cells. | Journal of cancer research and clinical oncology 20061001 |
| Nicotinic receptors mediate tumorigenic action of tobacco-derived nitrosamines on immortalized oral epithelial cells. | Cancer biology & therapy 20060501 |
| Acute and subacute effects of tobacco alkaloids, tobacco-specific nitrosamines and phenethyl isothiocyanate on N'-nitrosonornicotine metabolism in rats. | Toxicology 20051115 |
| Tobacco-specific nitrosamines in smokeless tobacco products marketed in India. | International journal of cancer 20050810 |
| Nicotine 5'-oxidation and methyl oxidation by P450 2A enzymes. | Drug metabolism and disposition: the biological fate of chemicals 20050801 |
| Duodenal acidity may increase the risk of pancreatic cancer in the course of chronic pancreatitis: an etiopathogenetic hypothesis. | JOP : Journal of the pancreas 20050310 |
| Effect of N'-nitrosonornicotine (NNN) on murine palatal fusion in vitro. | Toxicology 20050227 |
| Inhibition by N'-nitrosonornicotine of the catalytic activity of glutamate dehydrogenase in alpha-ketoglutarate amination. | Journal of enzyme inhibition and medicinal chemistry 20050201 |
| Cytochrome P450 2A-catalyzed metabolic activation of structurally similar carcinogenic nitrosamines: N'-nitrosonornicotine enantiomers, N-nitrosopiperidine, and N-nitrosopyrrolidine. | Chemical research in toxicology 20050101 |
| Tobacco-related-compound-induced nitrosative stress injury in the hamster cheek pouch. | Journal of dental research 20041201 |
| 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 |
| Effect of ethanol on lipid metabolism and epithelial permeability barrier of skin and oral mucosa in the rat. | Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology 20031101 |
| The permeability of oral leukoplakia. | European journal of oral sciences 20030801 |
| Nucleophilic reactions between thiols and a tobacco specific nitrosamine metabolite, 4-hydroxy-1-(3-pyridyl)-1-butanone. | Chemical research in toxicology 20030501 |
| [Cancer from snuff?]. | HNO 20030301 |
| Nicotine exposure and bronchial epithelial cell nicotinic acetylcholine receptor expression in the pathogenesis of lung cancer. | The Journal of clinical investigation 20030101 |
| Metabolism and pharmacokinetics of N'-nitrosonornicotine in the patas monkey. | Drug metabolism and disposition: the biological fate of chemicals 20021001 |
| Nitrosation of dietary myosmine as risk factor of human cancer. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20020801 |
| Role of human cytochrome P450 (CYP) in the metabolic activation of nitrosamine derivatives: application of genetically engineered Salmonella expressing human CYP. | Drug metabolism reviews 20020801 |
| Analysis of tobacco-specific nitrosamines in Moldovan cigarette tobacco. | Journal of agricultural and food chemistry 20020508 |
| Bacterial mutagenicity of some tobacco aromatic nitrogen bases and their mixtures. | Mutation research 20010531 |
| Preparation of pyridine-N-glucuronides of tobacco-specific nitrosamines. | Chemical research in toxicology 20010501 |
| Tobacco industry must not dump its high nitrosamine tobacco on poor countries. | BMJ (Clinical research ed.) 20010303 |
| Mutagenesis induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N-nitrosonornicotine in lacZ upper aerodigestive tissue and liver and inhibition by green tea. | Carcinogenesis 20010101 |
| Predicting the mutagenicity of tobacco-related N-nitrosamines in humans using 11 strains of Salmonella typhimurium YG7108, each coexpressing a form of human cytochrome P450 along with NADPH-cytochrome P450 reductase. | Environmental and molecular mutagenesis 20010101 |
| Smoke yields of tobacco-specific nitrosamines in relation to FTC tar level and cigarette manufacturer: analysis of the Massachusetts Benchmark Study. | Public health reports (Washington, D.C. : 1974) 20010101 |
| 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 |
| A tobacco smoke-derived nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, is activated by multiple human cytochrome P450s including the polymorphic human cytochrome P4502D6. | Carcinogenesis 19910701 |
| Comparative carcinogenicity in F344 rats of the tobacco-specific nitrosamines, N'-nitrosonornicotine and 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone. | Cancer research 19800201 |
| Carcinogenicity of N'-nitrosonornicotine in Sprague-Dawley rats. | Journal of the National Cancer Institute 19761201 |
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