The stereochemistry of hyoscine / by Harold King.

  • King, Harold.
Date:
1919]
Catalogue details

Licence: Public Domain Mark

Credit: The stereochemistry of hyoscine / by Harold King. Source: Wellcome Collection.

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    LXXXII. — The Stereochemistry of Hyoscine. By Harold King. In a former communication (this vol., p. 476), it was shown that by resolution of a weakly active hyoscine by means of sZ-a-bromo- 7r-camphorsulphonic acid, ^-hyoscine bromocamphorsulphonate was obtained as the more sparingly soluble salt. The base proved to be the enantiomorph of the therapeutically valuable /-hyoscine of commerce. The unexpected discovery was made, however, that d- and Z-hyoscines gave d/Z-oscine on hydrolysis with acid or alkali, whereas benzoyl-d'-oscine under similar conditions gave optically pure ^/-oscine. Furthermore, the d- and Z-oscine bases prepared by resolution of ^/Z-oscine were not racemised by acid or alkali. On these grounds, d- and Z-hyoscines were regarded as partially racemic esters, the optical activity being solely conditioned by the activity of the tropyl radicle. In the present communication, further confirmatory evidence is adduced. In 1908, Wolffenstein and Mamlock (Ber., 41, 730) showed that atropine (tropyltropine) can be converted into