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Percent Free Base Nicotine in the Tobacco Smoke Particulate Matter of Selected Commercial and Reference Cigarettes

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Department of Environmental and Biomolecular Systems, OGI School of Science & Engineering, Oregon Health & Science University, Portland, Oregon, 97291
Cite this: Chem. Res. Toxicol. 2003, 16, 8, 1014–1018
Publication Date (Web):July 24, 2003
https://doi.org/10.1021/tx0340596
Copyright © 2003 American Chemical Society
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    Abstract

    The available evidence suggests that most of the nicotine in mainstream tobacco smoke is in the smoke particle matter (PM) phase. Nicotine can exist in protonated and free base forms in the smoke PM, and αfb is the fraction of the PM nicotine that is in the free base form. Because only the free base form can volatilize from the smoke PM phase to the gas phase of an inhaled aerosol and because gaseous nicotine deposits rapidly in the respiratory tract (RT), the magnitude and rate of nicotine deposition in the RT will depend on αfb. The types of values that αfb can assume in the PM of cigarette smoke aerosols have not been well-known. The conventional view has been that mainstream cigarette smoke PM contains relatively little free base nicotine so that the cigarette smoker must absorb nicotine mostly from deposited particles. A prior study concluded that because cigarette smoke is at “pH 5.3”, there is very little free base nicotine in such smoke. A 1994 internal tobacco company document discusses the view that “smoke pH” values for cigarette smoke are “approximately 6.0”. This work uses volatility-based measurements to provide determinations of equilibrium nicotine αfb values for mainstream smoke PM from selected cigarettes. The effective pH (i.e., pHeff) of the smoke PM from selected brands of commercial cigarettes was found to span a range of 6.0−7.8 (nicotine αfb = 0.01−0.36), with all pHeff values much larger than 5.3 and most larger than 6.0.

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    11. Cai Chen and James F. Pankow. Gas/Particle Partitioning of Two Acid−Base Active Compounds in Mainstream Tobacco Smoke: Nicotine and Ammonia. Journal of Agricultural and Food Chemistry 2009, 57 (7) , 2678-2690. https://doi.org/10.1021/jf803018x
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    18. Omobola Ajoke Oladipupo, Dibyendu Dutta, Ngee Sing Chong. Analysis of chemical constituents in mainstream bidi smoke. BMC Chemistry 2019, 13 (1) https://doi.org/10.1186/s13065-019-0614-7
    19. Robert K Jackler, Divya Ramamurthi. Nicotine arms race: JUUL and the high-nicotine product market. Tobacco Control 2019, 28 (6) , 623-628. https://doi.org/10.1136/tobaccocontrol-2018-054796
    20. Véronique Perraud, Michael J. Lawler, Kurtis T. Malecha, Rebecca M. Johnson, David A. Herman, Norbert Staimer, Michael T. Kleinman, Sergey A. Nizkorodov, James N. Smith. Chemical characterization of nanoparticles and volatiles present in mainstream hookah smoke. Aerosol Science and Technology 2019, 53 (9) , 1023-1039. https://doi.org/10.1080/02786826.2019.1628342
    21. Michael McEwan, Steven Coburn, David Ghosh, Liam Simms, Lesley Giles, Dai Yuki, Madeleine Ashley, Ewald Roemer, Hyung-Ok Sohn, Christopher Proctor. Assessment of priority tobacco additives per the requirements of the EU Tobacco Products Directive (2014/40/EU): Part 3, Smoking behavior and plasma nicotine pharmacokinetics. Regulatory Toxicology and Pharmacology 2019, 104 , 29-38. https://doi.org/10.1016/j.yrtph.2019.02.012
    22. E. John, S. Coburn, C. Liu, J. McAughey, D. Mariner, K.G. McAdam, Z. Sebestyén, I. Bakos, S. Dóbé. Effect of temperature and humidity on the gas–particle partitioning of nicotine in mainstream cigarette smoke: A diffusion denuder study. Journal of Aerosol Science 2018, 117 , 100-117. https://doi.org/10.1016/j.jaerosci.2017.12.015
    23. William E Stephens. Comparing the cancer potencies of emissions from vapourised nicotine products including e-cigarettes with those of tobacco smoke. Tobacco Control 2018, 27 (1) , 10-17. https://doi.org/10.1136/tobaccocontrol-2017-053808
    24. Lukas Pichelstorfer, Werner Hofmann. Simulation of cigarette smoke dynamics in denuder tubes considering particle phase chemistry. Aerosol Science and Technology 2017, 51 (12) , 1419-1428. https://doi.org/10.1080/02786826.2017.1363867
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    26. Gail D. Anderson, Lingtak-Neander Chan. Pharmacokinetic Drug Interactions with Tobacco, Cannabinoids and Smoking Cessation Products. Clinical Pharmacokinetics 2016, 55 (11) , 1353-1368. https://doi.org/10.1007/s40262-016-0400-9
    27. Hillel R Alpert, Israel T Agaku, Gregory N Connolly. A study of pyrazines in cigarettes and how additives might be used to enhance tobacco addiction. Tobacco Control 2016, 25 (4) , 444-450. https://doi.org/10.1136/tobaccocontrol-2014-051943
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    37. H Klus, G Scherer, L Müller. Influence of Additives on Cigarette Related Health Risks. Beiträge zur Tabakforschung International/Contributions to Tobacco Research 2012, 25 (3) , 412-493. https://doi.org/10.2478/cttr-2013-0921
    38. Jihan M. Badr, Faida H. Bamane, Nagwa S. El-Shaer. APPLICATION OF HIGH PERFORMANCE THIN LAYER CHROMATOGRAPHY FOR DETERMINATION OF NICOTINE IN DIFFERENT BRANDS OF CIGARETTES. Journal of Liquid Chromatography & Related Technologies 2012, 35 (9) , 1213-1221. https://doi.org/10.1080/10826076.2011.619031
    39. D. L. McKinney, M. Gogova, B. D. Davies, V. Ramakrishnan, K. Fisher, W. H. Carter, H. T. Karnes, W. R. Garnett, S. S. Iyer, A. A. Somani, G. Kobal, W. H. Barr. Evaluation of the Effect of Ammonia on Nicotine Pharmacokinetics Using Rapid Arterial Sampling. Nicotine & Tobacco Research 2012, 14 (5) , 586-595. https://doi.org/10.1093/ntr/ntr257
    40. Andy Z. X. Zhu, Rachel F. Tyndale. Nicotine Metabolism and its Implications. 2012, 465-492. https://doi.org/10.1002/9783527630905.ch17
    41. Frank T. Leone, Sarah Evers-Casey. Developing a Rational Approach to Tobacco Use Treatment in Pulmonary Practice. Clinical Pulmonary Medicine 2012, 19 (2) , 53-61. https://doi.org/10.1097/CPM.0b013e318247cada
    42. M. Ongwandee, P. Sawanyapanich. Influence of relative humidity and gaseous ammonia on the nicotine sorption to indoor materials. Indoor Air 2012, 22 (1) , 54-63. https://doi.org/10.1111/j.1600-0668.2011.00737.x
    43. Michael L. Trehy, Wei Ye, Michael E. Hadwiger, Terry W. Moore, James F. Allgire, Jeffrey T. Woodruff, Shafiq S. Ahadi, John C. Black, Benjamin J. Westenberger. ANALYSIS OF ELECTRONIC CIGARETTE CARTRIDGES, REFILL SOLUTIONS, AND SMOKE FOR NICOTINE AND NICOTINE RELATED IMPURITIES. Journal of Liquid Chromatography & Related Technologies 2011, 34 (14) , 1442-1458. https://doi.org/10.1080/10826076.2011.572213
    44. J.H. Lauterbach, M. Bao, P.J. Joza, W.S. Rickert. Free-base nicotine in tobacco products. Part I. Determination of free-base nicotine in the particulate phase of mainstream cigarette smoke and the relevance of these findings to product design parameters. Regulatory Toxicology and Pharmacology 2010, 58 (1) , 45-63. https://doi.org/10.1016/j.yrtph.2010.05.007
    45. Mingliang Bao, Peter Joza, William S. Rickert, John H. Lauterbach. An improved headspace solid-phase microextraction method for the analysis of free-base nicotine in particulate phase of mainstream cigarette smoke. Analytica Chimica Acta 2010, 663 (1) , 49-54. https://doi.org/10.1016/j.aca.2010.01.036
    46. Huayu Xiong, Yunfei Zhao, Peng Liu, Xiuhua Zhang, Shengfu Wang. Electrochemical properties and the determination of nicotine at a multi-walled carbon nanotubes modified glassy carbon electrode. Microchimica Acta 2010, 168 (1-2) , 31-36. https://doi.org/10.1007/s00604-009-0258-8
    47. B. Dragoi, E. Dumitriu, C. Guimon, A. Auroux. Acidic and adsorptive properties of SBA-15 modified by aluminum incorporation. Microporous and Mesoporous Materials 2009, 121 (1-3) , 7-17. https://doi.org/10.1016/j.micromeso.2008.12.023
    48. Steven D. Stellman, Mirjana V. Djordjevic. Monitoring the tobacco use epidemic II. Preventive Medicine 2009, 48 (1) , S11-S15. https://doi.org/10.1016/j.ypmed.2008.09.004
    49. Jeffrey I. Seeman, Richard A. Carchman. The possible role of ammonia toxicity on the exposure, deposition, retention, and the bioavailability of nicotine during smoking. Food and Chemical Toxicology 2008, 46 (6) , 1863-1881. https://doi.org/10.1016/j.fct.2008.02.021
    50. Marc C. Willemsen, Andrée J. van Emst. Stimulerende middelen: tabak. 2008, 164-195. https://doi.org/10.1007/978-90-313-6554-8_6
    51. J. F. Pankow, W. E. Asher. SIMPOL.1: a simple group contribution method for predicting vapor pressures and enthalpies of vaporization of multifunctional organic compounds. Atmospheric Chemistry and Physics 2008, 8 (10) , 2773-2796. https://doi.org/10.5194/acp-8-2773-2008
    52. Michael Rabinoff, Nicholas Caskey, Anthony Rissling, Candice Park. Pharmacological and Chemical Effects of Cigarette Additives. American Journal of Public Health 2007, 97 (11) , 1981-1991. https://doi.org/10.2105/AJPH.2005.078014
    53. Kelley C. Barsanti, Wentai Luo, Lorne M. Isabelle, James F. Pankow, David H. Peyton. Tobacco smoke particulate matter chemistry by NMR. Magnetic Resonance in Chemistry 2007, 45 (2) , 167-170. https://doi.org/10.1002/mrc.1939
    54. Charlene H. Callicutt, Richard H. Cox, Frank Hsu, Robin D. Kinser, Susan W. Laffoon, Peter N. Lee, Kenneth F. Podraza, Edward B. Sanders, Jeffrey I. Seeman. The role of ammonia in the transfer of nicotine from tobacco to mainstream smoke. Regulatory Toxicology and Pharmacology 2006, 46 (1) , 1-17. https://doi.org/10.1016/j.yrtph.2006.05.008
    55. Hui-Ju Wu, Chin-Wen Chi, Tsung-Yun Liu. Effects of pH on Nicotine-Induced DNA Damage and Oxidative Stress. Journal of Toxicology and Environmental Health, Part A 2005, 68 (17-18) , 1511-1523. https://doi.org/10.1080/15287390590967478
    56. Janne Hukkanen, Pleyton Jacob, Neal L. Benowitz. Metabolism and Disposition Kinetics of Nicotine. Pharmacological Reviews 2005, 57 (1) , 79-115. https://doi.org/10.1124/pr.57.1.3
    57. Geoffrey Ferris Wayne, Gregory Connolly, Jack Henningfield. Assessing internal tobacco industry knowledge of the neurobiology of tobacco dependence. Nicotine & Tobacco Research 2004, 6 (6) , 927-940. https://doi.org/10.1080/14622200412331324839
    58. Alan K. Armitage, Michael Dixon, Barrie E. Frost, Derek C. Mariner, Neil M. Sinclair. The Effect of Tobacco Blend Additives on the Retention of Nicotine and Solanesol in the Human Respiratory Tract and on Subsequent Plasma Nicotine Concentrations during Cigarette Smoking. Chemical Research in Toxicology 2004, 17 (4) , 537-544. https://doi.org/10.1021/tx0340753
    59. David L. Ashley, James F. Pankow, Ameer D. Tavakoli, Clifford H. Watson. Approaches, Challenges, and Experience in Assessing Free Nicotine. , 437-456. https://doi.org/10.1007/978-3-540-69248-5_15
    60. Geoffrey Ferris Wayne, Carrie M. Carpenter. Tobacco Industry Manipulation of Nicotine Dosing. , 457-485. https://doi.org/10.1007/978-3-540-69248-5_16
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