Synthesis and Skeletal Muscle Relaxant Activity of Quaternary Ammonium Salts of Dantrolene and Clodanolene

A series of quaternary ammonium salts of dantrolene and clodanolene was prepared and evaluated for skeletal muscle relaxant activity. The quaternary ammonium salts exhibit greater aqueous solubility and, therefore, facilitate intravenous administration. One member of this series, although less effective orally, exhibited greater aqueous solubility than the sodium salt. When administered intravenously, it was a more potent antagonist of skeletal muscle contraction and yielded comparable therapeutic and muscle relaxant efficacy indexes.