Preparation and properties of some new tropeines / by H.A.D. Jowett and A.C.O. Hann.

  • Jowett, Hooper Albert Dickinson, 1870-1936.
Date:
[1906]
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: Preparation and properties of some new tropeines / by H.A.D. Jowett and A.C.O. Hann. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    or its salt is formed, and that the hydroxy-acid has a lower specific rotation and is less active physiologically than the lactone : C2H5-CH-CH-CH2-C*N(OH3) CO CH2 CH N \/ 0 >CH -> C2H5-CH—OH-CH2-C-N(CH3) C02H CH2-OH CH N >CH. This connection between chemical constitution and physiological action derives additional importance from the fact that pilocarpine acts specifically on the so-called nerve-endings in the heart. It was there- fore thought of interest to determine whether this difference in physiological action between a lactone and its corresponding hydroxy- acid could be observed in the case of other physiologically active bases. It has not been found possible, so far, to obtain a glyoxaline derivative similar to pilocarpine, and as atropine also acts on the nerve-endings of the heart, though antagonistically to pilocarpine, the tropeines were selected as suitable substances with which to investigate the difference in action between a lactone and its corresponding hydroxy-acid. For this purpose, it was decided to attempt the preparation of tropeines containing an acyl group similar to that existing in pilocarpine. Methylparaconyl- and terebyl-tropeines were therefore prepared, and the relation between these bases and pilocarpine is shown by the following formulae, where P is the pharmacophore or nitrogen-containing complex : ch,-ch-ch-co-p I o CH0 CO Methylparaconyltropeine. (CH3)2-C—CH-CO-P o ch2 \/ CO Terebyltropeine. C2H5-CH-CH-CH2-P CO ch2 \/ O Pilocarpine. In case these bases should prove to be physiologically inactive, an aromatic tropeine, similar to homatropine, but containing a lactone group, was also prepared. The relation between these bases is shown as under: CH-CO-P CH(OH)-CO-P Phthalidecarboxyltropeine. Homatropine (mandelyltropeine). At the same time it was thought of interest to investigate the physiological action of these and other tropeines and to determine to