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The smoke of cigarettes with high base content was examined for primary and secondary bases. As 4'-nitro-azobenzenecarboxamides- (4) (NABSA) the bases were separated by column and thin-layer chromatography and identified by melting points, RF-values, IR-spectra, retention times, mass-spectra, and elemental analyses. 27 primary and secondary bases were isolated and 24 of them identified. For the first time n-propylamine, n-butylamine, iso-butylamine, iso-pentylamine, b-phenethylamine, methyl ethylamine, diethylamine, methyl-b-phenethylamine, 1,2,5,6-tetrahydropyridine, aniline, 3-methylaminopyridine, and dihydrometanicotine were detected in cigarette smoke. Earlier results about the presence of pyrrolidine, piperidine, and 2-methylpyrrolidine in smoke could be confirmed. Presumably methyl-n-butylamine and methyl-iso-butylamine are to be found in tobacco smoke. One further amine was not identified.

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The cold pentane traps of the precipitation procedure described in the preceding paper (cotton wool trap, water trap, pentane traps) favour the formation of N-nitroso components and, as a result, the emergence of artefacts. If, however, the smoke sojourns in the aerosol state for a period of 40 seconds (compared to 5 seconds) also that part of condensate of smoke from cigarette tobaccos rich in nitrates and bases which is trapped on cotton wool at normal temperature, contains N-nitroso-dimethylamine and N-nitroso-pyrrolidine in quantities corresponding to 0.004 µg N-NO per cigarette. The formation of N-nitroso components in the smoke of tobaccos of high nitrate and base contents accordingly occurs during a gas phase reaction which is dependent on time.In conformity with the previously reported findings N-nitrosomethyl-n-butylamine was identified in the condensate gathered in pentane traps. Presumably, it has however to be regarded as an artefact produced by the precipitation system employed. Condensates collected in cold and acetone traps were found to contain more N-nitroso components than condensates precipitated simply by the gas phase reaction of the smoke. The quantity of N-nitroso components contained in condensates gathered in cold traps was found to increase during aging.Model experiments with pure substances showed that the formation of N-nitroso components in the gas phase requires the presence of a mixture of NO and NOThe competitive reaction of dimethylamine and methanol with the gaseous mixture of nitrogen oxides displays the prevailing formation of N-nitroso-dimethylamine. The yield of N-nitroso-dimethylamine in NO-air-mixtures is probably only dependent on the rate of the oxidation NO undergoes to NONitramines cannot occur in smoke.

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