A text-book of organic chemistry / by A.F. Holleman ; edited by A. Jamieson Walker ; assisted by Owen E. Mott ; with the co-operation of the author.

  • Arnold F. Holleman
Date:
1913
Catalogue details

Licence: In copyright

Credit: A text-book of organic chemistry / by A.F. Holleman ; edited by A. Jamieson Walker ; assisted by Owen E. Mott ; with the co-operation of the author. Source: Wellcome Collection.

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    §411] It can be regenerated from these two substances by the action of hydrochloric acid. Atropine is, therefore, the tropine ester of tropic acid, which is a-phenyl-0-hydroxypropionic acid, c0h5.ch< CH.OH COOII • The constitutions of atropine and tropine are: H2C—CH CH2 N • CH3 CHO • CO • CH • CHjOH IOC—CIO -CH2 Atropine c6H5 and I. II. H>C—CH CH2 I I N*CH;j C1IOH. I I H2C—CH CH2 Tropine This formula for tropine was proposed by Willstatter and is based on the decomposition-products of this substance. They are 1. Methylsuccinimide, (I.) indicating the presence of a tetra- hydropyrrole-nucleus.* 2. Tropidine, obtained through elimination of water by heat- ing with potassium hydroxide or dilute sulphuric acid: C8H15ON- II20 - C8Hk{N. Tropine Tropidine Tropidine can be converted into a-ethylpyridine (II.), proving that tropine contains a pyridine-ring. Ecgonine (412) is a carboxylated tropine: it breaks down to suberone (III.), indicating the presence of a ring of seven carbon atoms in the tropine molecule. It has also been estab- lished by the usual methods that tropine is a tertiary base, and contains a hydroxyl-group: CII2—CCA I. | >N*CH3 ; CH2—CCK II. C2II5 ; N CII2—CII2—CHix hi. i \co. CH2—CII2—CII2/ * Cf. footnote, 395.
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