Aza-Arenes in Tobacco Smoke12

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Abstract
Quinoline is a hepatocarcinogen in rats and has recently been found to be mutagenic in Salmonella typhimurium. Its presence and that of related compounds in tobacco and tobacco smoke were established. This report describes an analytical method for the qualitative and quantitative determination of quinolines and other basic aza-arenes in tobacco smoke. The method consists of solvent partitioning, column chromatography, and gas chromatography-mass spectrometry. High-pressure liquid chromatography (HPLC) and spectroscopic techniques were used to ascertain the identity of isomeric aza-arenes. Since quinoline was found to be the most abundant aza-arene in the smoke, 14C-quinoline was synthesized for use as an internal standard in quantitative determinations. The mainstream smoke of a U.S.-blended, 85-mm cigarette without filter tip contains 1.67 µ g of quinoline, 0.12 µ g of isoquinoline, and a total of 0.70 µ g of methylquinolines. Four isomers of benzoquinolines, azafluoranthenes, and azapyrenes were also quantitated. Sidestream smoke was found to contain about 11 times more quinoline than mainstream smoke. The analytical procedure was applied to various tobacco products as well as to unburned tobacco. Studies using cigarettes made entirely from cellulose showed that tobacco leaf proteins are major precursors for quinoline in the smoke. Non-selective reduction of quinoline levels in smoke can be effected by filtration; selective reduction can be achieved by use of tobacco of low protein content.