Isolation and ldentification of Aza-Arenes of Tobacco Smoke

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The nitrogen analogues of polynuclear aromatic hydrocarbons (aza-arenes) were isolated and identified in a basic fraction of cigarette smoke condensate. Silicic acid chromatography removed the predominant nicotine alkaloids, while gel chromatography on Bio-Beads S-X12 in benzene effectively separated the aza-arenes from interfering aliphatic compounds. In addition, the gel columns separated the aza-arenes by ring number and degree of alkylation on the basis of an adsorption-type mechanism. These gel characteristics facilitated the identifications of a large number of isomeric aza-arenes. Compounds identified included 2-vinylpyridine, 3-vinylpyridine and 2-phenylpyridine as well as quinoline, isoquinoline, 4-azafluorene, benzoquinolines, benzoisoquinolines, 1-azafluoranthene, 7-azafluoranthene, 4-aza-pyrene, 7- azaindole, pyrroloquinoline and their mono-, di- and trimethyl derivatives. All eight possible isomers of benzoquinoline and benzoisoquinoline were found, four of which are being reported for the first time. Evidence was also found for the probable presence of 5,6-benzo-7-azaindole.

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  • 1. Shubik P. and J. L. Hartwell: Survey of compounds which have been tested for carcinogenic activity; U.S. Public Health Service U.S. Government Printing Office Washington D.C. Pub. 149 Suppl. 2 1969; 1968-69 Vol. 1972; 1970-1971 Vol. 1974

  • 2. McKay J. F. J. H. Weber and D. K. Latham: Characterization of nitrogen bases in high-boiling petroleum distillates; Anal. Chem. 48 (1976) 891-898.

  • 3. Cautreels W. and K. van Cauwenberghe: Determination of organic compounds in airborne particulate matter by gas chromatography- mass spectrometry; Atmos. Environ. 10 (1976) 447-457-4. Sawicki E. J. E. Meeker and M. J. Morgan: Polynuclear aza compounds in automobile exhaust; Arch. Environ. Health 11 (1975) 773-775.

  • 5. Schmeltz I. and D. Hoffmann: Nitrogen-containing compounds in tobacco and tobacco smoke; Chem. Rev. 77 (1977) 295-311.

  • 6. Dong M. I. Schmeltz E. Jacobs and D. Hoffmann: Aza-arenes in tobacco smoke; J. Anal. Toxicol. 2 (1978) 21-25.

  • 7. Klus H. and H. Kuhn: Beitrag zur Kenntnis der schwadt basischen und schwach sauren polycyclischen aromatischen Kohlenwasserstoffe im Tabakrauch; Fachl. Mitt. Austria Tabakwerke A.G. Heft 17 (1977) 348-368. 78

  • 8. Swain A. P J. E. Cooper and R. L. Stedman: Large scale fractionation of cigarette smoke condensate for chemical and biological investigation; Cancer Res. 29 (1969) 579-583.

  • 9. Snook M. E. W J. Chamberlain R. F. Severson and 0. T. Chonyk: Chromatographic concentration of polynuclear aromatic hydrocarbons of tobacco smoke; Anal. Chem. 47 (1975) 1155-1157.

  • 10. Snook M. E.: Gel elution of heterocyclic analogues of polynuclear aromatic hydrocarbons from Bio-Beads; Anal. Chim. Acta 99 (1978) 299-304.

  • 11. Poindexter E. H. Jr. and R. D. Carpenter: The isolation of barman and norharman from tobacco and cigarette smoke; Phytochem. 1 (1962) 215-221.

  • 12. Horner Leopold: Die Synthese isomerer Pyrrod:tinoline und eines weiteren Isomeren des Vomipyrins (Ober Strychnosalkaloide XXI); Justus Liebigs Ann. Chem. 540 (1939) 73-83.

  • 13. Sawicki. E. T. W. Stanley J. D. Pfaff and W. C. Elbert: Thin-layer d:tromatographic separation and analysis of polynuclear azaheterocyclic compounds; Anal. Chim. Acta 31 (1964) 359-375.

  • 14. Campbell N. and K. R. Reid: The synthesis and properties of 2-azafluoranthene; J. Chem. Soc. 19584743-4746.

  • 15. Testa A. and P. Testa: The nitrogenous heterocycles in the smoke condensate (continued); Annates de la Direction des Études et de l'Équipement (SEITA) 3 (1965) 103-108.

  • 16. Witkop B.: Studies on carboline anhydronium bases; J. Amer. Chem. Soc. 75 (1953) 3361-3370.

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