Veratrum alkaloids LI. Hypotensive-emetic relationships in the unanesthetized dog among analogs of the protoveratrines

✍ Scribed by Lawrence C. Weaver; W. Ralph Jones; S. Morris Kupchan

• Publisher: John Wiley and Sons
• Year: 1962
• Tongue: English
• Weight: 372 KB
• Volume: 51
• Category: Article
• ISSN: 0022-3549
• DOI: 10.1002/jps.2600511207

✦ Synopsis

protoverine 3-isobutyrate 6,7,16-triacetate 15-nicotinate (XVI) in 57 ml. of methanol was allowed to stand at room temperature for 16 hours. Evaporation to dryness left a resin which resisted attempts a t purification by column chromatography, but which yielded to preparative paper chromatography. The resin was dissolved in chloroform and applied to Whatman No. 4 paper (19 sheets, 6 X 18 inches) pretreated with phosphate buffer of pH 3.5. After development for 2.5 hours with the iso- octane solvent system4 and drying, a chloroform solution of Bromphenol Blue was sprayed over the papers as usual. The desired band was cut from the sheets and extracted with 2% methanolchloroform in a Soxhlet extractor for 2 hours. The extract was shaken with dilute ammonium hydroxide to liberate the free base and remove the dye, and the chloroform solution was washed with water. The chloroform solution was dried over anhydrous sodium sulfate and evaporated to yield a colorless resin weighing 205 mg., which was shown to be homogeneous by paper ~hromatography.~ Crystallization from acetone-ether gave colorless prisms weighing 139 mg., m.p. 227-229" decompn. Re-