The structure of the ring-opened N beta-propyl-ajmaline (Neo-Gilurytmal) at physiological pH is obviously responsible for its better absorption and bioavailability when compared with ajmaline (Gilurytmal).
Prajmaline, the semisynthetic propyl derivative of ajmaline, shows a much better bioavailability when compared with the Rauvolfia alkaloid ajmaline. Early NMR and IR-studies, fluorescence spectroscopic investigations and extraction experiments combined with ion-pair chromatography proved the thesis of a tautomeric equilibrium between an aldehyde-amine and a quaternary carbinol-ammonium component. The aim of this study was to confirm this thesis by HPLC-separation and by structure-determination of both tautomeric compounds.
Hinse
C
C
Institut für Pharmazie, Johannes Gutenberg-Universität, Mainz, Germany. stoeckig@mail.uni-mainz.de
Stöckigt
J
J
D000404:Ajmaline / Q000737:chemistry* / Q000493:pharmacokinetics*; D000889:Anti-Arrhythmia Agents / Q000737:chemistry* / Q000493:pharmacokinetics*; D001682:Biological Availability; D002851:Chromatography, High Pressure Liquid; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D007408:Intestinal Absorption; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011219:Prajmaline / Q000737:chemistry* / Q000493:pharmacokinetics*; D013329:Structure-Activity Relationship
D000889:Anti-Arrhythmia Agents; D007202:Indicators and Reagents; D000404:Ajmaline; D011219:Prajmaline