F. M. Berger, M. Kletzkin, B. J. Ludwig
Mar 1, 1960
Citations
2
Influential Citations
39
Citations
Journal
Annals of the New York Academy of Sciences
Abstract
Administration of meprobamate to suitable patients produces both tranquilization and muscular relaxation (Berger, 1956). Since elimination of one of these two actions not only could yield new and useful drugs, but might also shed some light on the interrelation between psychic and somatic tension, numerous compounds chemically related to meprobamate (Berger, 1954) were synthesized and subjected to pharmacological evaluation. Of these, N-isopropyl-2-methyl-Zpropyl-l , 3-propanediol dicarbamate (FIGURE l), called carisoprodol (Soma, Rela), which differs from meprobamate in having an isopropyl group in place of a hydrogen atom on one of the carbamyl nitrogens, appeared of unusual interest (Berger, 1959). This relatively simple substitution yielded a compound that was surprisingly unlike meprobamate in pharmacological properties (Berger el al., 1959). Carisoprodol not only had an entirely different profile of effects on the central nervous system but, in addition, unexpectedly exhibited analgesic properties of an unusual kind. I t melts without decomposition at 92O to 94" C. and dissolves in water to the extent of 0.3 mg./ml. at 25" C. and 1.4 mg./ml. at 50" C. It is readily soluble in common organic solvents, but almost insoluble in liquid fats. On boiling with strong acid or alkali, carisoprodol is hydrolyzed to ammonia, isopropylamine, carbon dioxide, and 2-methyl-2-propyl-l , 3-propanediol. I t is stable in dilute acid and alkali, and is not altered by gastric or intestinal juices at 37" C.