N-Nitrosonornicotine (BioDeep_00001871825)
Main id: BioDeep_00000011192
代谢物信息卡片
3-(1-nitrosopyrrolidin-2-yl)pyridine
化学式: C9H11N3O (177.0902)
中文名称: (2S)-N’-亚硝基去甲烟碱, 去甲基烟碱亚硝胺
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1CC(N(C1)N=O)C2=CN=CC=C2
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
描述信息
D009676 - Noxae > D002273 - Carcinogens
同义名列表
数据库引用编号
11 个数据库交叉引用编号
- ChEBI: CHEBI:80502
- KEGG: C16452
- PubChem: 27919
- ChEMBL: CHEMBL434108
- CAS: 53759-22-1
- CAS: 84237-38-7
- CAS: 16543-55-8
- CAS: 80508-23-2
- PubChem: 47205748
- NIKKAJI: J2.745F
- KNApSAcK: 80502
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Thomas Meikopoulos, Olga Begou, Theodoros Panagoulis, Eleni Kontogiannidou, Dimitrios G Fatouros, John H Miller, Georgios Theodoridis, Helen Gika. UHPLC-MS/MS method for the simultaneous determination of nicotine and tobacco-specific nitrosamines NNN and NNK for use in preclinical studies.
Analytical and bioanalytical chemistry.
2022 Nov; 414(27):7865-7875. doi:
10.1007/s00216-022-04319-6. [PMID: 36163593] - Nikola Pluym, Gerhard Scherer, Jeffery S Edmiston, Xiaohong C Jin, Mohamadi Sarkar, Max Scherer. Assessment of the Exposure to NNN in the Plasma of Smokeless Tobacco Users.
Chemical research in toxicology.
2022 04; 35(4):663-669. doi:
10.1021/acs.chemrestox.1c00431. [PMID: 35298127] - Sampada S Nikam, Murari Gurjar, Hitesh Singhavi, Anand Patil, Arjun Singh, Peter Villalta, Pankaj Chaturvedi, Samir S Khariwala, Vikram Gota, Irina Stepanov. Simultaneous analysis of urinary total 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol, N'-nitrosonornicotine, and cotinine by liquid chromatography-tandem mass-spectrometry.
Scientific reports.
2021 10; 11(1):20007. doi:
10.1038/s41598-021-99259-z. [PMID: 34625573] - Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040. [PMID: 33910017] - Baoyun Xia, Benjamin C Blount, Tonya Guillot, Christina Brosius, Yao Li, Dana M Van Bemmel, Heather L Kimmel, Cindy M Chang, Nicolette Borek, Kathryn C Edwards, Charlie Lawrence, Andrew Hyland, Maciej L Goniewicz, Brittany N Pine, Yang Xia, John T Bernert, B Rey De Castro, John Lee, Justin L Brown, Stephen Arnstein, Diane Choi, Erin L Wade, Dorothy Hatsukami, Gladys Ervies, Angel Cobos, Keegan Nicodemus, Dana Freeman, Stephen S Hecht, Kevin Conway, Lanqing Wang. Tobacco-Specific Nitrosamines (NNAL, NNN, NAT, and NAB) Exposures in the US Population Assessment of Tobacco and Health (PATH) Study Wave 1 (2013-2014).
Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco.
2021 02; 23(3):573-583. doi:
10.1093/ntr/ntaa110. [PMID: 32716026] - Rumasha N T Kankanamage, Abhisek Brata Ghosh, Di Jiang, Karmel Gkika, Tia Keyes, Laura A Achola, Steven Suib, James F Rusling. Metabolites of Tobacco- and E-Cigarette-Related Nitrosamines Can Drive Cu2+-Mediated DNA Oxidation.
Chemical research in toxicology.
2020 08; 33(8):2072-2086. doi:
10.1021/acs.chemrestox.0c00027. [PMID: 32672941] - Zhongbang Song, Xueyi Sui, Meiyun Li, Yulong Gao, Wenzheng Li, Lu Zhao, Feng Li, Xuefeng Yao, Chunming Liu, Bingwu Wang. Development of a nornicotine-reduced flue-cured tobacco line via EMS mutagenesis of nicotine N-demethylase genes.
Plant signaling & behavior.
2020; 15(2):1710053. doi:
10.1080/15592324.2019.1710053. [PMID: 31900036] - Yi Wang, Sreekanth Chanickal Narayanapillai, Qi Hu, Naomi Fujioka, Chengguo Xing. Detection and quantification of 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB) from smoker albumin and its potential as a surrogate biomarker of tobacco-specific nitrosamines exposure and bioactivation.
Toxicology letters.
2019 Sep; 311(?):11-16. doi:
10.1016/j.toxlet.2019.04.020. [PMID: 31026483] - Alpana K Gupta, Sonam Tulsyan, Mausumi Bharadwaj, Ravi Mehrotra. Grass roots approach to control levels of carcinogenic nitrosamines, NNN and NNK in smokeless tobacco products.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2019 Feb; 124(?):359-366. doi:
10.1016/j.fct.2018.12.011. [PMID: 30543893] - Ivann K C Martinez, Nicole R L Sparks, Joseph V Madrid, Henry Affeldt, Madeline K M Vera, Bir Bhanu, Nicole I Zur Nieden. Video-based kinetic analysis of calcification in live osteogenic human embryonic stem cell cultures reveals the developmentally toxic effect of Snus tobacco extract.
Toxicology and applied pharmacology.
2019 01; 363(?):111-121. doi:
10.1016/j.taap.2018.11.006. [PMID: 30468815] - Gabriela Bustamante, Bin Ma, Galina Yakovlev, Katrina Yershova, Chap Le, Joni Jensen, Dorothy K Hatsukami, Irina Stepanov. Presence of the Carcinogen N'-Nitrosonornicotine in Saliva of E-cigarette Users.
Chemical research in toxicology.
2018 08; 31(8):731-738. doi:
10.1021/acs.chemrestox.8b00089. [PMID: 30019582] - Lucie Loukotková, Linda S VonTungeln, Michelle Vanlandingham, Gonçalo Gamboa da Costa. A simple and highly sensitive UPLC-ESI-MS/MS method for the simultaneous quantification of nicotine, cotinine, and the tobacco-specific carcinogens N'-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in serum samples.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2018 Jan; 1072(?):229-234. doi:
10.1016/j.jchromb.2017.11.022. [PMID: 29179064] - Jing Yang, Steven G Carmella, Stephen S Hecht. Analysis of N'-nitrosonornicotine enantiomers in human urine by chiral stationary phase liquid chromatography-nanoelectrospray ionization-high resolution tandem mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2017 Feb; 1044-1045(?):127-131. doi:
10.1016/j.jchromb.2017.01.008. [PMID: 28107699] - Verena Liedschulte, Joanne Deborah Schwaar, Hélène Laparra, Aline Vuarnoz, Bérangère Philippon, Nicolas Bakaher, Nicolas Sierro, Lucien Bovet, Gerhard Lang, Simon Goepfert. Identification of CYP82E21 as a functional nicotine N-demethylase in tobacco flowers.
Phytochemistry.
2016 Nov; 131(?):9-16. doi:
10.1016/j.phytochem.2016.08.004. [PMID: 27596288] - Nahid Moghbel, BoMi Ryu, Peter J Cabot, Angela Ratsch, Kathryn J Steadman. In vitro cytotoxicity of Nicotiana gossei leaves, used in the Australian Aboriginal smokeless tobacco known as pituri or mingkulpa.
Toxicology letters.
2016 07; 254(?):45-51. doi:
10.1016/j.toxlet.2016.05.011. [PMID: 27178269] - Dorothy K Hatsukami, Herbert Severson, Amanda Anderson, Rachael Isaksson Vogel, Joni Jensen, Berry Broadbent, Sharon E Murphy, Steven Carmella, Stephen S Hecht. Randomised clinical trial of snus versus medicinal nicotine among smokers interested in product switching.
Tobacco control.
2016 May; 25(3):267-74. doi:
10.1136/tobaccocontrol-2014-052080. [PMID: 25991608] - Bin Cai, Huihua Ji, Franklin F Fannin, Lowell P Bush. Contribution of Nicotine and Nornicotine toward the Production of N'-Nitrosonornicotine in Air-Cured Tobacco (Nicotiana tabacum).
Journal of natural products.
2016 Apr; 79(4):754-9. doi:
10.1021/acs.jnatprod.5b00678. [PMID: 26959866] - Stephen S Hecht, Irina Stepanov, Steven G Carmella. Exposure and Metabolic Activation Biomarkers of Carcinogenic Tobacco-Specific Nitrosamines.
Accounts of chemical research.
2016 Jan; 49(1):106-14. doi:
10.1021/acs.accounts.5b00472. [PMID: 26678241] - Delshanee Kotandeniya, Steven G Carmella, Makenzie E Pillsbury, Stephen S Hecht. Combined analysis of N'-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in the urine of cigarette smokers and e-cigarette users.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2015 Dec; 1007(?):121-6. doi:
10.1016/j.jchromb.2015.10.012. [PMID: 26595795] - Min-ting Li, Yong-yan Zhu, Li Li, Wen-na Wang, Yong-guan Yin, Quan-hong Zhu. Molecularly imprinted polymers on a silica surface for the adsorption of tobacco-specific nitrosamines in mainstream cigarette smoke.
Journal of separation science.
2015 Jul; 38(14):2551-7. doi:
10.1002/jssc.201500193. [PMID: 25914259] - Pramod Upadhyaya, Stephen S Hecht. Quantitative analysis of 3'-hydroxynorcotinine in human urine.
Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco.
2015 May; 17(5):524-9. doi:
10.1093/ntr/ntu206. [PMID: 25324430] - Irina Stepanov, Erin Sebero, Renwei Wang, Yu-Tang Gao, Stephen S Hecht, Jian-Min Yuan. Tobacco-specific N-nitrosamine exposures and cancer risk in the Shanghai Cohort Study: remarkable coherence with rat tumor sites.
International journal of cancer.
2014 May; 134(10):2278-83. doi:
10.1002/ijc.28575. [PMID: 24243522] - Samir S Khariwala, Steven G Carmella, Irina Stepanov, Patricia Fernandes, Amy Anne Lassig, Bevan Yueh, Dorothy Hatsukami, Stephen S Hecht. Elevated levels of 1-hydroxypyrene and N'-nitrosonornicotine in smokers with head and neck cancer: A matched control study.
Head & neck.
2013 Aug; 35(8):1096-100. doi:
10.1002/hed.23085. [PMID: 22807150] - Jian-Min Yuan, Aleksandar D Knezevich, Renwei Wang, Yu-Tang Gao, Stephen S Hecht, Irina Stepanov. Urinary levels of the tobacco-specific carcinogen N'-nitrosonornicotine and its glucuronide are strongly associated with esophageal cancer risk in smokers.
Carcinogenesis.
2011 Sep; 32(9):1366-71. doi:
10.1093/carcin/bgr125. [PMID: 21734256] - Panneerselvam Vijayaraj, Jayaraja Sabarirajan, Vasanthi Nachiappan. Enhanced phospholipase B activity and alteration of phospholipids and neutral lipids in Saccharomyces cerevisiae exposed to N-nitrosonornicotine.
Antonie van Leeuwenhoek.
2011 Mar; 99(3):567-77. doi:
10.1007/s10482-010-9526-1. [PMID: 21046464] - Ramsey S Lewis, Steven W Bowen, Matthew R Keogh, Ralph E Dewey. Three nicotine demethylase genes mediate nornicotine biosynthesis in Nicotiana tabacum L.: functional characterization of the CYP82E10 gene.
Phytochemistry.
2010 Dec; 71(17-18):1988-98. doi:
10.1016/j.phytochem.2010.09.011. [PMID: 20977974] - Dominique Kavvadias, Gerhard Scherer, Francis Cheung, Graham Errington, Jim Shepperd, Mike McEwan. Determination of tobacco-specific N-nitrosamines in urine of smokers and non-smokers.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals.
2009 Dec; 14(8):547-53. doi:
10.3109/13547500903242883. [PMID: 19747086] - Irina Stepanov, Steven G Carmella, Anna Briggs, Louise Hertsgaard, Bruce Lindgren, Dorothy Hatsukami, Stephen S Hecht. Presence of the carcinogen N'-nitrosonornicotine in the urine of some users of oral nicotine replacement therapy products.
Cancer research.
2009 Nov; 69(21):8236-40. doi:
10.1158/0008-5472.can-09-1084. [PMID: 19843845] - Michael Urban, Gerhard Scherer, Dominique Kavvadias, Heinz-Werner Hagedorn, Shixia Feng, Richard Serafin, Sunil Kapur, Raheema Muhammad, Yan Jin, Paul Mendes, Hans Roethig. Quantitation of N'-nitrosonornicotine (NNN) in smokers' urine by liquid chromatography-tandem mass spectrometry.
Journal of analytical toxicology.
2009 Jun; 33(5):260-5. doi:
10.1093/jat/33.5.260. [PMID: 19671245] - Irina Stepanov, Steven G Carmella, Shaomei Han, Angela Pinto, Andrew A Strasser, Caryn Lerman, Stephen S Hecht. 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.
2009 Jan; 11(1):99-105. doi:
10.1093/ntr/ntn004. [PMID: 19246447] - Gang Chen, Ryan W Dellinger, Dongxiao Sun, Thomas E Spratt, Philip Lazarus. Glucuronidation of tobacco-specific nitrosamines by UGT2B10.
Drug metabolism and disposition: the biological fate of chemicals.
2008 May; 36(5):824-30. doi:
10.1124/dmd.107.019406. [PMID: 18238858] - Ramsey S Lewis, Anne M Jack, Jerry W Morris, Vincent J M Robert, Lily B Gavilano, Balazs Siminszky, Lowell P Bush, Alec J Hayes, Ralph E Dewey. RNA interference (RNAi)-induced suppression of nicotine demethylase activity reduces levels of a key carcinogen in cured tobacco leaves.
Plant biotechnology journal.
2008 May; 6(4):346-54. doi:
10.1111/j.1467-7652.2008.00324.x. [PMID: 18282175] - Irina Stepanov, Stephen S Hecht. 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.
2008 Apr; 17(4):945-8. doi:
10.1158/1055-9965.epi-07-2711. [PMID: 18398035] - Lily B Gavilano, Balazs Siminszky. Isolation and characterization of the cytochrome P450 gene CYP82E5v2 that mediates nicotine to nornicotine conversion in the green leaves of tobacco.
Plant & cell physiology.
2007 Nov; 48(11):1567-74. doi:
10.1093/pcp/pcm128. [PMID: 17923451] - Diana Porubin, Stephen S Hecht, Zhong-ze Li, Maria Gonta, Irina Stepanov. Endogenous formation of N'-nitrosonornicotine in F344 rats in the presence of some antioxidants and grape seed extract.
Journal of agricultural and food chemistry.
2007 Aug; 55(17):7199-204. doi:
10.1021/jf0712191. [PMID: 17637060] - Juan Arredondo, Alexander I Chernyavsky, Sergei A Grando. SLURP-1 and -2 in normal, immortalized and malignant oral keratinocytes.
Life sciences.
2007 May; 80(24-25):2243-7. doi:
10.1016/j.lfs.2007.01.003. [PMID: 17280689] - Juan Arredondo, Alex I Chernyavsky, Sergei A Grando. The nicotinic receptor antagonists abolish pathobiologic effects of tobacco-derived nitrosamines on BEP2D cells.
Journal of cancer research and clinical oncology.
2006 Oct; 132(10):653-63. doi:
10.1007/s00432-006-0113-9. [PMID: 16835749] - Stefan Tyroller, Wolfgang Zwickenpflug, Charlotte Thalheim, Elmar Richter. Acute and subacute effects of tobacco alkaloids, tobacco-specific nitrosamines and phenethyl isothiocyanate on N'-nitrosonornicotine metabolism in rats.
Toxicology.
2005 Nov; 215(3):245-53. doi:
10.1016/j.tox.2005.07.011. [PMID: 16118032] - Christopher A Squier, Mary J Kremer, Philip W Wertz. 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.
2003 Nov; 32(10):595-9. doi:
10.1034/j.1600-0714.2003.00198.x. [PMID: 14632934] - Jolán Bánóczy, Christopher A Squier, Mary Kremer, Philip W Wertz, György Kövesi, Béla Szende, Csaba Dombi. The permeability of oral leukoplakia.
European journal of oral sciences.
2003 Aug; 111(4):312-5. doi:
10.1034/j.1600-0722.2003.00042.x. [PMID: 12887396] - Pramod Upadhyaya, Cheryl L Zimmerman, Stephen S Hecht. Metabolism and pharmacokinetics of N'-nitrosonornicotine in the patas monkey.
Drug metabolism and disposition: the biological fate of chemicals.
2002 Oct; 30(10):1115-22. doi:
10.1124/dmd.30.10.1115. [PMID: 12228188] - P Upadhyaya, E J McIntee, S S Hecht. Preparation of pyridine-N-glucuronides of tobacco-specific nitrosamines.
Chemical research in toxicology.
2001 May; 14(5):555-61. doi:
10.1021/tx000262e. [PMID: 11368554] - M M von Pressentin , M Chen, J B Guttenplan. 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.
2001 Jan; 22(1):203-6. doi:
10.1093/carcin/22.1.203. [PMID: 11159761] - E J McIntee, S S Hecht. Metabolism of N'-nitrosonornicotine enantiomers by cultured rat esophagus and in vivo in rats.
Chemical research in toxicology.
2000 Mar; 13(3):192-9. doi:
10.1021/tx990171l. [PMID: 10725116] - H B Jenson, P Heard, M P Moyer. Evaluation of the effect of smokeless tobacco purified products and extracts on latent Epstein-Barr virus.
Toxicology.
1999 Mar; 133(1):35-42. doi:
10.1016/s0300-483x(99)00003-7. [PMID: 10413192] - N Trushin, S S Hecht. Stereoselective metabolism of nicotine and tobacco-specific N-nitrosamines to 4-hydroxy-4-(3-pyridyl)butanoic acid in rats.
Chemical research in toxicology.
1999 Feb; 12(2):164-71. doi:
10.1021/tx980213q. [PMID: 10027794] - J F Cloutier, A Castonguay. Modulation of DNA repair by various inhibitors of DNA synthesis following 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) induced DNA damage.
Chemico-biological interactions.
1998 Mar; 110(1-2):7-25. doi:
10.1016/s0009-2797(97)00114-2. [PMID: 9566722] - S G Carmella, A Borukhova, D Desai, S S Hecht. Evidence for endogenous formation of tobacco-specific nitrosamines in rats treated with tobacco alkaloids and sodium nitrite.
Carcinogenesis.
1997 Mar; 18(3):587-92. doi:
10.1093/carcin/18.3.587. [PMID: 9067560] - B Hasséus, M Wallström, B G Osterdahl, J M Hirsch, M Jontell. Immunotoxic effects of smokeless tobacco on the accessory cell function of rat oral epithelium.
European journal of oral sciences.
1997 Feb; 105(1):45-51. doi:
10.1111/j.1600-0722.1997.tb00179.x. [PMID: 9085028] - D Hoffmann, A A Melikian, E L Wynder. Scientific challenges in environmental carcinogenesis.
Preventive medicine.
1996 Jan; 25(1):14-22. doi:
10.1006/pmed.1996.0007. [PMID: 8778753] - G S Schuster, G B Caughman, T R Dirksen. Alteration of epithelial cell lipid synthesis by N-nitrosonornicotine.
In vitro cellular & developmental biology. Animal.
1995 Apr; 31(4):295-9. doi:
10.1007/bf02634004. [PMID: 7795848] - V Nachiappan, S I Mufti, A Chakravarti, C D Eskelson, R Rajasekharan. Lipid peroxidation and ethanol-related tumor promotion in Fischer-344 rats treated with tobacco-specific nitrosamines.
Alcohol and alcoholism (Oxford, Oxfordshire).
1994 Sep; 29(5):565-74. doi:
10.1093/oxfordjournals.alcalc.a045585. [PMID: 7811340] - G Andersson, G Björnberg, M Curvall. Oral mucosal changes and nicotine disposition in users of Swedish smokeless tobacco products: a comparative study.
Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology.
1994 Apr; 23(4):161-7. doi:
10.1111/j.1600-0714.1994.tb01106.x. [PMID: 8046653] - S Knasmüller, F Kassie, E Zöhrer, M Kundi, D G McCoy, R Schulte-Hermann. Effects of ethanol treatment on DNA damage induced in Escherichia coli K-12 in various organs of mice by N-nitro-sonornicotine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N-nitrosopyrrolidine.
Carcinogenesis.
1994 Feb; 15(2):263-70. doi:
10.1093/carcin/15.2.263. [PMID: 8313517] - P A Larsson, J M Hirsch, J S Gronowitz, A Vahlne. Inhibition of herpes simplex virus replication and protein synthesis by non-smoked tobacco, tobacco alkaloids and nitrosamines.
Archives of oral biology.
1992 Nov; 37(11):969-78. doi:
10.1016/0003-9969(92)90069-k. [PMID: 1334651] - H Dokko, P S Min, H M Cherrick, N H Park. Effect of smokeless tobacco and tobacco-related chemical carcinogens on survival of ultraviolet light-inactivated herpes simplex virus.
Oral surgery, oral medicine, and oral pathology.
1991 Apr; 71(4):464-8. doi:
10.1016/0030-4220(91)90431-b. [PMID: 1646981] - P R Padma, A J Amonkar, S V Bhide. Effect of long-term treatment of two tobacco-specific N-nitrosamines on the vitamin A status of mice.
Nutrition and cancer.
1991; 15(3-4):217-20. doi:
10.1080/01635589109514129. [PMID: 1866315] - U J Nair, N Ammigan, M Nagabhushan, A J Amonkar, S V Bhide. Effect of vitamin A status of rats on metabolizing enzymes after exposure to tobacco extract or N'-nitrosonornicotine.
IARC scientific publications.
1991; ?(105):525-8. doi:
. [PMID: 1855910] - N Ammigan, U J Nair, A J Amonkar, S V Bhide. Effect of tobacco extract and N'-nitrosonornicotine on the carcinogen metabolising enzymes under different dietary vitamin B status.
Cancer letters.
1990 Jul; 52(2):153-9. doi:
10.1016/0304-3835(90)90258-y. [PMID: 2379138] - G S Schuster, S Lubas, J F Erbland, B B Singh. Binding and uptake of N-nitrosonornicotine by oral epithelial cells.
Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology.
1990 Mar; 19(3):114-8. doi:
10.1111/j.1600-0714.1990.tb00808.x. [PMID: 2341979] - P R Padma, V S Lalitha, A J Amonkar, S V Bhide. Anticarcinogenic effect of betel leaf extract against tobacco carcinogens.
Cancer letters.
1989 Jun; 45(3):195-202. doi:
10.1016/0304-3835(89)90077-3. [PMID: 2731162] - T E Spratt, N Trushin, D Lin, S S Hecht. Analysis for N2-(pyridyloxobutyl)deoxyguanosine adducts in DNA of tissues exposed to tritium-labeled 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N'-nitrosonornicotine.
Chemical research in toxicology.
1989 May; 2(3):169-73. doi:
10.1021/tx00009a008. [PMID: 2519721] - P R Padma, A J Amonkar, S V Bhide. Antimutagenic effects of betel leaf extract against the mutagenicity of two tobacco-specific N-nitrosamines.
Mutagenesis.
1989 Mar; 4(2):154-6. doi:
10.1093/mutage/4.2.154. [PMID: 2659927] - N Ammigan, U J Nair, A J Amonkar, S V Bhide. Modulations in the biotransformation of tobacco extract and N'-nitrosonornicotine under differential dietary protein status.
Journal of biochemical toxicology.
1989; 4(1):7-13. doi:
10.1002/jbt.2570040103. [PMID: 2769698] - G S Schuster, J F Erbland, S D Wyrick, B B Singh. Phorbol ester binding to oral epithelial cells in the presence of retinoic acid or N-nitrosonornicotine.
Cytobios.
1988; 54(216):53-60. doi:
". [PMID: 3208542] - L Domellöf, M Andersson, H Tjälve, S Veals, N Trushin, S S Hecht. Distribution and metabolism of N'-nitrosonornicotine in the miniature pig.
Carcinogenesis.
1987 Nov; 8(11):1741-7. doi:
10.1093/carcin/8.11.1741. [PMID: 3664969] - D Hoffmann, J D Adams, K D Brunnemann. A critical look at N-nitrosamines in environmental tobacco smoke.
Toxicology letters.
1987 Jan; 35(1):1-8. doi:
10.1016/0378-4274(87)90079-8. [PMID: 3810668] - G S Schuster, J F Erbland, S D Wyrick, B B Singh. Oral epithelial cell lipid synthesis in the presence of retinoic acid or nitrosonornicotine.
Journal of oral pathology.
1986 Sep; 15(8):430-3. doi:
10.1111/j.1600-0714.1986.tb00652.x. [PMID: 3100741] - M I Díaz Gómez, D Tamayo, J A Castro. Administration of N-nitrosodimethylamine, N-nitrosopyrrolidine, or N'-nitrosonornicotine to nursing rats: their interactions with liver and kidney nucleic acids from sucklings.
Journal of the National Cancer Institute.
1986 Jun; 76(6):1133-6. doi:
. [PMID: 2423736] - S V Bhide, U J Nair, J Nair, B Spiegelhalder, R Preussmann. N-nitrosamines in the saliva of tobacco chewers or masheri users.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
1986 Apr; 24(4):293-7. doi:
10.1016/0278-6915(86)90005-0. [PMID: 3732974] - A Castonguay, H Tjälve, N Trushin, R d'Argy, G Sperber. Metabolism and tissue distribution of tobacco-specific N-nitrosamines in the marmoset monkey (Callithrix jacchus).
Carcinogenesis.
1985 Nov; 6(11):1543-50. doi:
10.1093/carcin/6.11.1543. [PMID: 4053274] - D Hoffmann, A Melikian, J D Adams, K D Brunnemann, N J Haley. New aspects of tobacco carcinogenesis.
Carcinogenesis; a comprehensive survey.
1985; 8(?):239-56. doi:
NULL. [PMID: 3986825] - B Löfberg, E B Brittebo, H Tjälve. Localization and binding of N'-nitrosonornicotine metabolites in the nasal region and in some other tissues of Sprague-Dawley rats.
Cancer research.
1982 Jul; 42(7):2877-83. doi:
NULL. [PMID: 7083177] - S S Hecht, R Young. Regiospecificity in the metabolism of the homologous cyclic nitrosamines, N'-nitrosonornicotine and N'-nitrosoanabasine.
Carcinogenesis.
1982; 3(10):1195-9. doi:
10.1093/carcin/3.10.1195. [PMID: 7172419] - D Hoffmann, A Castonguay, A Rivenson, S S Hecht. Comparative carcinogenicity and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N'-nitrosonornicotine in Syrian golden hamsters.
Cancer research.
1981 Jun; 41(6):2386-93. doi:
. [PMID: 7237437] - S S Hecht, D Lin, C B Chen. Comprehensive analysis of urinary metabolites of N'-nitrosonornicotine.
Carcinogenesis.
1981; 2(9):833-8. doi:
10.1093/carcin/2.9.833. [PMID: 7296768] - S S Hecht, C B Chen, D Hoffmann. Metabolic beta-hydroxylation and N-oxidation of N'-nitrosonornicotine.
Journal of medicinal chemistry.
1980 Nov; 23(11):1175-8. doi:
10.1021/jm00185a005. [PMID: 7452667] - W J Waddell, C Marlowe. Localization of [14C]nitrosonornicotine in tissues of the mouse.
Cancer research.
1980 Oct; 40(10):3518-23. doi:
. [PMID: 7002288]
