Abstract
For the first time, we show the presence of nitro substituted naphthalenes in both mainstream and sidestream tobacco smoke using electron monochromator-mass spectrometry. Only one mainstream smoke sample showed the presence of 1-nitronaphthalene (1-NN) at 20 pg/cigarette, while all of the sidestream smoke samples showed the presence of 1-NN at levels ranging from 0.40 to 0.60 ng/cigarette and 2-NN at quantities ranging from 1 to 2 ng/cigarette. Additionally, these levels showed a ratio of ~1:3 for 1-NN to 2-NN which demonstrates that the formation of 2-NN is favored under sidestream combustion conditions. No larger ring structure (>2) nitro-aromatics were identified.
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References
Baker RR (1976) Gas velocities inside a burning cigarette. Nature 264:167–169. doi:10.1038/264167b0
Baldwin RM, Shultz MA, Buckpitt AR (2004) Bioactivation of the pulmonary toxicants naphthalene and 1-nitronaphthalene by rat CYP2F4. J Pharmacol Exp Ther 312:857–865. doi:10.1124/jpet.104.075440
Bamford HA, Baker JE (2003) Nitro-polycyclic aromatic hydrocarbon concentrations and sources in urban and suburban atmospheres of the mid-Atlantic region. Atmos Environ 37(15):2077–2091. doi:10.1016/S1352-2310(03)00102-X
Chen PX, Moldoveanu SC (2003) Mainstream smoke chemical analyses for 2R4F Kentucky reference cigarette. Beitr Tabakforsch Int 20(7):448–458
Dane AJ, Havey CD, Voorhees KJ (2006) The detection of nitro pesticides in mainstream and sidestream cigarette smoke using electron monochromator-mass spectrometry. Anal Chem 78(10):3227–3233. doi:10.1021/ac060328w
Davis DL, Nielson MT (2002) Tobacco: production, chemistry, and technology. Blackwell Science, Malden
Havey CD, McCormick RL, Hayes RR, Dane AJ, Voorhees KJ (2006) Analysis of Nitro-polycyclic aromatic hydrocarbons in conventional diesel and Fischer-Tropsch diesel fuel emissions using electron monochromator-mass spectrometry. Anal Chem 78:4894–4900. doi:10.1021/ac060400q
Hoffmann D, Rathkamp G (1970) Quantitative determination of nitrobenzenes in cigarette smoke. Anal Chem 42(13):1643–1647. doi:10.1021/ac60295a049
Kielhorn J, Wahnschaffe U, Mangelsdorf I (2003) Selected nitro- and nitro-oxy-polycyclic aromatic hydrocarbons. World Health Organization, Geneva
Laramee JA, Mazurkiewicz P, Berkout V, Deinzer ML (1996) Electron-monochromator mass spectrometer instrument for negative ion analysis of electronegative compounds. Mass Spectrom Rev 15:15–42. doi :10.1002/(SICI)1098-2787(1996)15:1<15::AID-MAS2>3.0.CO;2-E
Laramee JA, Cody RB, Deinzer ML (2000) Discrete energy electron capture negative ion mass spectrometry. In: Meyers RA (ed) Encyclopedia of analytical chemistry. Wiley, Chichester, pp 11651–11679
Lebedevas S, Vaicekauskas A, Suškov P (2007) Presumptions of effective operation of diesel engines running on RME biodiesel. Research on kinetics of combustion of RME biodiesel. Transport XXII(2):126–133
O’Neill IK, Brunnemann KD, Dodet B, Hoffmann D (1987) Passive smoking. International Agency for Research on Cancer, Lyon
Pitts JN Jr, van Cauwenberghe KA, Grosjean D, Schmid JP, Fitz DR, Belser WL et al (1978) Atmospheric reactions of polycyclic aromatic hydrocarbons: facile formation of mutagenic nitro derivatives. Science 202(4367):515–519. doi:10.1126/science.705341
Ramdahl T, Zielinska B, Arey J, Atkinson R, Winer AM, Pitts JN Jr (1986) Ubiquitous occurrence of 2-nitrofluoranthene and 2-nitropyrene in air. Nature 321(6068):425–427. doi:10.1038/321425a0
Rosenkranz HS, Mermelstein R (1983) Mutagenicity and genotoxicity of nitroarenes. All nitro-containing chemicals were not created equal. Mutat Res 114:217–267
Verschoyle RD, Carthew P, Wolf CR, Dinsdale D (1993) 1-nitronaphthalene toxicity in rat lung and liver: effects of inhibiting and inducing cytochrome P450 activity. Toxicol Appl Pharmacol 122(2):208–213. doi:10.1006/taap.1993.1189
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The authors wish to thank Phillip Morris USA and the Colorado Tobacco Research Program for their generous support of this study.
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Havey, C.D., Dane, A.J., Abbas-Hawks, C. et al. Detection of nitro-polycyclic aromatic hydrocarbons in mainstream and sidestream tobacco smoke using electron monochromator-mass spectrometry. Environ Chem Lett 7, 331–336 (2009). https://doi.org/10.1007/s10311-008-0174-x
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DOI: https://doi.org/10.1007/s10311-008-0174-x