Nicotine, anabasine and related derivatives

The various Nicotiana species, particularly N. rustica, N. tabacum, N. sylvestris and N. glauca, contain different Nicotiana alkaloids in various proportions. The most important of these alkaloids are nicotine (1), nornicotine (2) and anabasine 

Although the French chemist Gohory prepared a raw tobacco product containing nicotine as early as 1571, the pure alkaloid was first isolated by Posselt and Reimann in 1828. The structure was proved by Pinner in 1893 by decomposition (Pinner, 1893a 1893b), and later by Pictet and Rotschy (1904) by synthesis. 

Nicotine is converted by oxidation with chromic acid or permanganate into nicotinic acid (4), and by quaternisation, methylation and subsequent oxidation 

These investigations, and also those of Pinner (1893a 1893b) on the decomposition of the bromination products of nicotine, proved the presence of the pyridine and N-methylpyrrolidine moieties in the nicotine molecule. 

Investigations on the determination of the absolute configuration of nicotine showed that the nicotine molecule contains an asymmetric centre of S-con-figuration  

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