Partial synthesis of 6'-hydroxycinchonine and its antiarrhythmic activity in mice.
The synthesis of 6'-hydroxycinchonine [8R,9S)-cinchonan-6',9-diol] was achieved by demethylating quinidine with boron tribromide in dichloromethane at -75 degrees C. The antiarrhythmic activities of 6'-hydroxycinchonine and quinidine were compared following the infusion of aconitine into the tail veins of mice to induce arrhythmias. Comparative ED50 and LD50 studies for quinidine and 6'-hydroxycinchonine revealed equivalent antiarrhythmic potencies for the two drugs but a smaller acute toxicity for 6'-hydroxycinchonine.
D000157:Aconitine / Q000494:pharmacology; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis*; D001145:Arrhythmias, Cardiac / Q000139:chemically induced; D002930:Cinchona Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D011802:Quinidine / Q000494:pharmacology
D000889:Anti-Arrhythmia Agents; D002930:Cinchona Alkaloids; D011802:Quinidine; D000157:Aconitine