<abstract xmlns="http://www.w3.org/1999/xhtml"><p> A method was developed for the enrichment of carbazoles from cigarette smoke. It involves a distribution between two solvent systems, column chromatography, and, finally, separation of a carbazole concentrate into individual components by gas chromatography. The major components in the chromatogram were collected after the final separation and were then identified by mass spectra. Since the latter method showed similar fragmentation patterns for five carbazoles and 2- and 3-phenylindoles, mass spectra appeared especially suitable for their identification. Carbazole, 1-methylcarbazole, 4-methylcarbazole, 3-phenylindole, a mixture of 2- and 3-methylcarbazole and, tentatively, a dimethyl- or ethylcarbazole and 2-phenylindole were identified in cigarette smoke. The relevancy of mass spectra for the identification of carbazoles and 2- and 3-phenylindoles is discussed. For the quantitative analysis of carbazoles and 3-phenylindole, carbazole-10-C<sup>14</sup> was employed as internal standard. The radioactive compound was synthesized on a microscale from phenylhydrazine-1-C14 by the Borsche method with a 58% yield. The smoke of 100 U.S. nonfilter cigarettes of 85 mm length contains 100 µg of carbazole, 23 µg of 1-methylcarbazole, 19 µg of 2- and 3-methylcarbazole, 9.8 µg of 4-methylcarbazole and 31 µg of 3-phenylindole. The concentrations of the tentatively identified dimethyl-, or ethylcarbazole and 2-phenylindole were below 1.0 µg.</p></abstract>

A method was developed for the enrichment of carbazoles from cigarette smoke. It involves a distribution between two solvent systems, column chromatography, and, finally, separation of a carbazole concentrate into individual components by gas chromatography. The major components in the chromatogram were collected after the final separation and were then identified by mass spectra. Since the latter method showed similar fragmentation patterns for five carbazoles and 2- and 3-phenylindoles, mass spectra appeared especially suitable for their identification. Carbazole, 1-methylcarbazole, 4-methylcarbazole, 3-phenylindole, a mixture of 2- and 3-methylcarbazole and, tentatively, a dimethyl- or ethylcarbazole and 2-phenylindole were identified in cigarette smoke. The relevancy of mass spectra for the identification of carbazoles and 2- and 3-phenylindoles is discussed. For the quantitative analysis of carbazoles and 3-phenylindole, carbazole-10-C14 was employed as internal standard. The radioactive compound was synthesized on a microscale from phenylhydrazine-1-C14 by the Borsche method with a 58% yield. The smoke of 100 U.S. nonfilter cigarettes of 85 mm length contains 100 µg of carbazole, 23 µg of 1-methylcarbazole, 19 µg of 2- and 3-methylcarbazole, 9.8 µg of 4-methylcarbazole and 31 µg of 3-phenylindole. The concentrations of the tentatively identified dimethyl-, or ethylcarbazole and 2-phenylindole were below 1.0 µg.

Chemical Studies on Tobacco Smoke: VI. The Determination of Carbazoles in Cigarette Smoke

Division of Environmental Cancerigenesis, Sloan-Kettering Institute for Cancer Research, New York, NY, USA

Contributions to Tobacco & Nicotine Research

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A method was developed for the enrichment of carbazoles from cigarette smoke. It involves a distribution between two solvent systems, column chromatography,...

Chemical Studies on Tobacco Smoke: VI. The Determination of Carbazoles in Cigarette Smoke

Published Online: Jul 03, 2014

Page range: 253 - 263

DOI: https://doi.org/10.2478/cttr-2013-0193

© Beiträge zur Tabakforschung International

This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.