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Assessment of Tobacco-specific N-Nitrosamines in Tobacco Products¹

Division of Environmental Carcinogenesis, Naylor Dana Institute for Disease Prevention, American Health Foundation, Valhalla, New York 10595

Tobacco-specific nonvolatile N-nitrosamines in tobacco and in fresh mainstream and sidestream smoke of cigarettes and cigars were quantitatively determined with a thermal energy analyzer. The smoke was trapped in ascorbic acid solution buffered at pH 4.5 and extracted with dichloromethane, and the organic phase was chromatographed and analyzed by high-performance liquid chromatography-thermal energy analyzer methodology (sensitivity, 250 pg/injection). The nonvolatile nitrosamines were further enriched by repeated chromatography and positively identified by gas-liquid chromatography-mass spectrometry. [2'-¹⁴C]N'-nitrosonornicotine served as internal standard for the quantitative analysis.

The tobacco of five different cigarettes contained between 0.22 and 7.0 ppm of the carcinogenic N'-nitrosonornicotine, 0.13 and 0.74 ppm of the carcinogenic 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone, and 0.44 to 3.2 ppm of the newly identified N'-nitrosoanatabine. In unaged mainstream and sidestream smoke of the same cigarettes, values ranged between 0.24 and 3.7 and 0.15 and 6.1 µg/cigarette for N'-nitrosonornicotine, between 0.11 and 0.42 and 0.19 and 0.66 µg/cigarette for 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone, and between 0.33 and 4.6 and 0.15 and 1.5 µg/cigarette for N'-nitrosoanatabine, respectively. The relatively high concentrations of these carcinogenic N-nitrosamines in sidestream smoke are discussed as possible tobacco-specific indicators for indoor pollution.

¹ Supported by National Cancer Institute Contract NO1-CP-55666 and American Cancer Society Grant BC56, The Alexander Ralston Peacock Memorial Grant. This is Paper 62 in the series, "Chemical Studies on Tobacco Smoke."

² To whom requests for reprints should be addressed, at Division of Environmental Carcinogenesis, Naylor Dana Institute for Disease Prevention, Dana Road, American Health Foundation, Valhalla, N. Y. 10595.

³ Recipient of National Cancer Institute Research Career Development Award NO-5K04CA00124.

Received 1/11/79. Accepted 4/ 3/79.