(S)-Nicotine (1) is present together with a number of minor alkaloids in tobacco and a wide variety of other plants. Driedleaves of the tobacco plants Nicotiana rustica and N. tabacum contain as much as 2–8% of (S)-nicotine.1 Interest in the actions of nicotine has remained high over the past century, primarily because of the widespread exposure of people to nicotine through recreational use of tobacco products. First isolated in 1828,2 the correct structure of nicotine was not proposed until 1883 by Pinner.3 Pictet and Rotschy are accredited with first synthesizing the alkaloid in 1904.4 Whidby and Seeman reported in 1976 that the preferred (>90%) configuration of the N-methyl group in nicotine is (R) under a variety of experimental conditions.5 In fresh N. tabacum, the alkaloid mixture typically consists of 93% (S)-nicotine (1), 3.9% (S)-anatabine (2), 2.4% (S)-nornicotine (3), and 0.5% (S)-anabasine (4) (Fig. 1).~6
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