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A study of tobacco carcinogenesis. 17. Tobacco-specific nitrosamines: occurrence, formation, carcinogenicity, and metabolism

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    A study of tobacco carcinogenesis. 17. Tobacco-specific nitrosamines: occurrence, formation, carcinogenicity, and metabolism
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    Accounts of Chemical Research

    Cite this: Acc. Chem. Res. 1979, 12, 3, 92–98
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    https://doi.org/10.1021/ar50135a003
    Published March 1, 1979
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    This article is cited by 40 publications.

    1. Jiu Ai, Matthew Hassink, Kenneth M. Taylor, Peter Kuklenyik, Liza Valentín-Blasini, Clifford Watson. Tobacco-Specific Nitrosamines in Current Commercial Large Cigars, Cigarillos, and Little Cigars. Chemical Research in Toxicology 2024, 37 (2) , 220-226. https://doi.org/10.1021/acs.chemrestox.3c00211
    2. Ming-Der Su. Role of Spin−Orbit Coupling and Symmetry in Triplet Carbenic Addition Chemistry. The Journal of Physical Chemistry 1996, 100 (11) , 4339-4349. https://doi.org/10.1021/jp950290j
    3. Jabez Raju Battu, Somala Karthik, Gummudala Yashaswini, Himanshu Thakur, Alagesan Keerthana, M. P. Shireesh Kumar, Morthala Shankara Sai Reddy. LC–MS/MS analysis of carcinogenic tobacco-specific nitrosamines in Spodoptera litura using the QuEChERS method. Scientific Reports 2023, 13 (1) https://doi.org/10.1038/s41598-023-37656-2
    4. Fadzrul Johani, Mohd Majid, Muhammad Azme, Azmawati Nawi. Cytochrome P450 2A6 whole-gene deletion (CYP2A6*4 ) polymorphism reduces risk of lung cancer: A meta-analysis. Tobacco Induced Diseases 2020, 18 (June) https://doi.org/10.18332/tid/122465
    5. Hossein Roohi, Mahjoubeh Jahantab. Adsorption sensitivity of nanocrystalline B-substituted H-ZSM-5 and alkali metal-exchanged M-ZSM-5 zeolites towards parent nitrosamine: A B97D study. Computational and Theoretical Chemistry 2015, 1066 , 76-87. https://doi.org/10.1016/j.comptc.2015.05.015
    6. Scott Appleton, Raquel M. Olegario, Peter J. Lipowicz. TSNA levels in machine-generated mainstream cigarette smoke: 35years of data. Regulatory Toxicology and Pharmacology 2013, 66 (2) , 197-207. https://doi.org/10.1016/j.yrtph.2013.03.013
    7. Irina Stepanov, Aleksandar Knezevich, Liqin Zhang, Clifford H Watson, Dorothy K Hatsukami, Stephen S Hecht. Carcinogenic tobacco-specific N -nitrosamines in US cigarettes: three decades of remarkable neglect by the tobacco industry. Tobacco Control 2012, 21 (1) , 44-48. https://doi.org/10.1136/tc.2010.042192
    8. Mohamad Sleiman, Lara A. Gundel, James F. Pankow, Peyton Jacob, Brett C. Singer, Hugo Destaillats. Formation of carcinogens indoors by surface-mediated reactions of nicotine with nitrous acid, leading to potential thirdhand smoke hazards. Proceedings of the National Academy of Sciences 2010, 107 (15) , 6576-6581. https://doi.org/10.1073/pnas.0912820107
    9. Jing Yang, Li Li Ma, Bin Shen, Jian Hua Zhu. Capturing Nitrosamines in Environment by Zeolite. Materials and Manufacturing Processes 2007, 22 (6) , 750-757. https://doi.org/10.1080/10426910701385382
    10. Dariusz Pogocki, Tomasz Ruman, Magdalena Danilczuk, Marek Danilczuk, Monika Celuch, Elżbieta Wałajtys-Rode. Application of nicotine enantiomers, derivatives and analogues in therapy of neurodegenerative disorders. European Journal of Pharmacology 2007, 563 (1-3) , 18-39. https://doi.org/10.1016/j.ejphar.2007.02.038
    11. L. Q. Sheng, L. Ding, H. W. Tong, G. P. Yong, X. Z. Zhou, S. M. Liu. Determination of Nicotine-Related Alkaloids in Tobacco and Cigarette Smoke by GC-FID. Chromatographia 2005, 62 (1-2) , 63-68. https://doi.org/10.1365/s10337-005-0567-y
    12. Ying Wang, Shi-lu Zhou, Jia-rong Xia, Jun Xue, Jia-hui Xu, Jian-hua Zhu. Trapping and degradation of volatile nitrosamines on cyclodextrin and zeolites. Microporous and Mesoporous Materials 2004, 75 (3) , 247-254. https://doi.org/10.1016/j.micromeso.2004.07.025
    13. Jibao Cai, Baizhan Liu, Ping Lin, Qingde Su. Fast analysis of nicotine related alkaloids in tobacco and cigarette smoke by megabore capillary gas chromatography. Journal of Chromatography A 2003, 1017 (1-2) , 187-193. https://doi.org/10.1016/j.chroma.2003.07.003
    14. Eduardo De Stefani, Paul Brennan, Alvaro Ronco, Luis Fierro, Pelayo Correa, Paolo Boffetta, Hugo Deneo-Pellegrini, Enrique Barrios. Food groups and risk of lung cancer in Uruguay. Lung Cancer 2002, 38 (1) , 1-7. https://doi.org/10.1016/S0169-5002(02)00147-2
    15. C.J Smith, T.A Perfetti, M.A Rumple, A Rodgman, D.J Doolittle. “IARC Group 2B carcinogens” reported in cigarette mainstream smoke. Food and Chemical Toxicology 2001, 39 (2) , 183-205. https://doi.org/10.1016/S0278-6915(00)00164-2
    16. C.J Smith, T.A Perfetti, M.A Mullens, A Rodgman, D.J Doolittle. “IARC Group 2B Carcinogens” reported in cigarette mainstream smoke. Food and Chemical Toxicology 2000, 38 (9) , 825-848. https://doi.org/10.1016/S0278-6915(00)00066-1
    17. E. De Stefani, P. Boffetta, F. Oreggia, M. Mendilaharsu, H. Deneo-Pellegrini. Smoking patterns and cancer of the oral cavity and pharynx: a case–control study in Uruguay. Oral Oncology 1998, 34 (5) , 340-346. https://doi.org/10.1016/S1368-8375(98)00014-1
    18. Eduardo De Stefani, Luis Fierro, Enrique Barrios, Alvaro Ronco. Tobacco, alcohol, diet and risk of non-Hodgkin's lymphoma: a case-control study in Uruguay. Leukemia Research 1998, 22 (5) , 445-452. https://doi.org/10.1016/S0145-2126(97)00194-X
    19. Eduardo De Stefani, Luis Fierro, Pelayo Correa, Julio Carzoglio, Hugo Deneo-Pellegrini, Diego Zavala, Elizabeth Fontham, Vivien Chen. Type of tobacco and risk of lung cancer: a case-control study from Uruguay. Lung Cancer 1992, 8 (1) , 21-27. https://doi.org/10.1016/0169-5002(92)90213-4
    20. P. J. Baldry, C. F. Cullis, D. Goring, M. M. Hirschler. The combustion of cigarette paper. Fire and Materials 1988, 12 (1) , 25-33. https://doi.org/10.1002/fam.810120105
    21. L.I. Belen'Kii. The Literature of Heterocyclic Chemistry, Part III. 1988, 269-396. https://doi.org/10.1016/S0065-2725(08)60264-0
    22. Charlene W. Bayer, Marilyn S. Black. Thermal desorption/gas chromatographic/mass spectrometric analysis of volatile organic compounds in the offices of smokers and nonsmokers. Biological Mass Spectrometry 1987, 14 (8) , 363-367. https://doi.org/10.1002/bms.1200140803
    23. Joseph E. Saavedra. RECENT SYNTHETIC APPLICATIONS OF N-NITROSAMINES AND RELATED COMPOUNDS. Organic Preparations and Procedures International 1987, 19 (2-3) , 83-159. https://doi.org/10.1080/00304948709356181
    24. W.S. Rickert, J.C. Robinson, N.E. Collishaw. A study of the growth and decay of cigarette smoke NOx in ambient air under controlled conditions. Environment International 1987, 13 (6) , 399-408. https://doi.org/10.1016/0160-4120(87)90003-1
    25. L. Griciute, M. Castegnaro, J.C. Béréziat, J.R.P. Cabral. Influence of ethyl alcohol on the carcinogenic activity of N-nitrosonornicotine. Cancer Letters 1986, 31 (3) , 267-275. https://doi.org/10.1016/0304-3835(86)90147-3
    26. Mohammed A. Hannan, Adnan El-Yazigi, Manik Paul, D. Phillip Gibson, Robert L. Phillips. Genotoxicity of ‘shamma’, a chewing material suspected of causing oral cancer in Saudi Arabia. Mutation Research/Genetic Toxicology 1986, 169 (1-2) , 41-46. https://doi.org/10.1016/0165-1218(86)90016-9
    27. George M. Strunz, John A. Findlay. Chapter 3 Pyridine and Piperidine Alkaloids. 1985, 89-183. https://doi.org/10.1016/S0099-9598(08)60194-7
    28. A.T. Sipahimalani, M.S. Chadha, S.V. Bhide, A.I. Pratap, J. Nair. Detection of N-nitrosamines in the saliva of habitual chewers of tobacco. Food and Chemical Toxicology 1984, 22 (4) , 261-264. https://doi.org/10.1016/0278-6915(84)90003-6
    29. L.A. Damani, D.E. Case. Metabolism of Heterocycles. 1984, 223-246. https://doi.org/10.1016/B978-008096519-2.00009-6
    30. . Volume 1 References. 1984, 673-731. https://doi.org/10.1016/B978-008096519-2.00129-6
    31. Aaron Blair, Bertram W. Berney, Marian F. Heid, Deborah W. White. Causes of Death among Workers in the Tobacco Industry. Archives of Environmental Health: An International Journal 1983, 38 (4) , 223-228. https://doi.org/10.1080/00039896.1983.10545807
    32. G. David McCoy, Stephen S. Hecht, Elena C. McCoy. Comparison of microsomal inducer pretreatment on the in vitro α‐hydroxylation and mutagenicity of N‐nitrosopyrrolidine in rat and hamster liver. Environmental Mutagenesis 1982, 4 (3) , 221-230. https://doi.org/10.1002/em.2860040304
    33. R.F. Severson, K.L. McDuffie, R.F. Arrendale, G.R. Gwynn, J.F. Chaplin, A.W. Johnson. Rapid method for the analysis of tobacco nicotine alkaloids. Journal of Chromatography A 1981, 211 (1) , 111-121. https://doi.org/10.1016/S0021-9673(00)81179-6
    34. Richard R. Baker. Product formation mechanisms inside a burning cigarette. Progress in Energy and Combustion Science 1981, 7 (2) , 135-153. https://doi.org/10.1016/0360-1285(81)90008-3
    35. Edmond J. La Voie, Stephen S. Hecht. Chemical Carcinogens: In Vitro Metabolism and Activation. 1981, 155-249. https://doi.org/10.1016/B978-0-12-312401-2.50010-4
    36. G.David McCoy, Stephen S. Hecht, Ernst L. Wynder. The roles of tobacco, alcohol, and diet in the etiology of upper alimentary and respiratory tract cancers. Preventive Medicine 1980, 9 (5) , 622-629. https://doi.org/10.1016/0091-7435(80)90034-1
    37. Dietrich Hoffmann, T.C. Tso, Gio B. Gori. The less harmful cigarette. Preventive Medicine 1980, 9 (2) , 287-296. https://doi.org/10.1016/0091-7435(80)90089-4
    38. G. David McCoy, Chi-hong B. Chen, Stephen S. Hecht. INFLUENCE OF MODIFIERS OF MFO ACTIVITY ON THE IN VITRO METABOLISM OF CYCLIC NITROSAMINES. 1980, 1189-1192. https://doi.org/10.1016/B978-0-12-187702-6.50111-0
    39. Stephen S. Hecht, Chi-Hong B. Chen, G.David McCoy, Dietrich Hoffmann, Lennart Domellöf. α-Hydroxylation of N-nitrosopyrrolidine and N′-nitrosonornicotine by human liver microsomes. Cancer Letters 1979, 8 (1) , 35-41. https://doi.org/10.1016/0304-3835(79)90020-X
    40. S. S. HECHT, C.‐H. B. CHEN, D. HOFFMANN. ChemInform Abstract: A STUDY OF TOBACCO CARCINOGENESIS. 17. TOBACCO‐SPECIFIC NITROSAMINES: OCCURRENCE, FORMATION, CARCINOGENICITY, AND METABOLISM. Chemischer Informationsdienst 1979, 10 (34) https://doi.org/10.1002/chin.197934342
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    Cite this: Acc. Chem. Res. 1979, 12, 3, 92–98
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ar50135a003
    Published March 1, 1979
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