Licence: In copyright
Credit: The plant alkaloids / by Thomas Anderson Henry. Source: Wellcome Collection.
Provider: This material has been provided by the Royal College of Physicians of Edinburgh. The original may be consulted at the Royal College of Physicians of Edinburgh.
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![but this was eventually effected by Pictet and Kotschy with the formation of tetrahydronicotyrine, which proved to be identical with inactive nicotine, obtained by heating solutions of natural nicotine hydrochloride or sulphate in sealed tubes at 180°-250°. The synthetic base was resolved into the optical antipodes by fractional crystallisation of the d-ditartrate, and in this way bnicotine identical with the natural alkaloid was obtained. The (Z-nicotine simultaneously prepared had b.p. 245-5°-246-5°/729 mm. DIO 1-0171 and [a]f + 163-17°. Nicotiniine, CioH;i4N2. This isomeride of nicotine was isolated by Pictet and Rotschy ^ from crude nicotine by treating the latter with nitrous acid, which converts nicotimine into the crystalline nitroso-compound, from which the alkaloid was regenerated as a colourless alkaline oil, b.p. 250°-255°, soluble in water. The hydrochloride, platinichloride, aurichloride, and mercurichloride are crystalline; the picrate forms thick prisms, m.p. 163°. Pictet “ has suggested that nicotimine contains two pyridine nuclei, and is represented by the following formula : CH:CH.C—CH.CHg.CH, I II I r CH:N—CH NH.CH2.CH2 Nicotimine (Pictet) Nicoteine, C10H42N2. In addition to the foregoing, tobacco contains two alkaloids which are not volatile in steam and remain in the aqueous tobacco extract when this is steam-distilled, viz. nicoteine and nicotelline.^ The former, separated by extraction with ether, is a colourless alkaline liquid, b.p. 266°-267°, D^^'® 1‘0778, [ajo—46° 4P, miscible with water or ether, and furnishes well-crystallised laevorotatory salts : the picrate has m.p. 165°. Nicoteine forms a dimethiodide, is oxidised by nitric acid to nicotinic acid, and reacts as a pyrrole derivative, whence Pictet has suggested that it has the following constitution since on heating with silver oxide in water it yields dihydronicotyrine (ii). 1 Berichte, 1901, 34, 696. 2 Arch. Pharm. 1906, 244, 375. 2 Pictet and Rotschy, Berichte, 1901, 34, 696. * Arch. Pharm. 1906, 244, 376.](https://iiif.wellcomecollection.org/image/b2196189x_0058.jp2/full/800%2C/0/default.jpg)
