Comparative Pharmacology of Isomeric Saligenins and Their Bromine Derivatives

Abstract

Macht and Dunning described the chemical and physiological properties of mono-brom-hydroxy-benzyl alcohol, or mono-brom-saligenin. 1 This compound, which has been named Bromsalizol, was the mono-brom derivative of ortho-hydroxy-benzyl alcohol. Inasmuch as 3 isomers of saligenin with the hydroxyl OH and benzyl CH₂OH groups in the ortho, meta and para positions, respectively, are possible, they and their mono-brom derivatives were prepared in these laboratories and investigated with regard to their comparative pharmacology. The structural formulae of the 3 saligenin isomers and their corresponding mono-brom derivatives are as follows:

The melting point of ortho-saligenin was 85°-87°; of meta-sal-igenin, 70°-71°; of para-saligenin, 116°; of mono-brom-ortho-saligenin, 108°-109°; of mono-brom-meta-saligenin, 124°; and of mono-brom-para-saligenin, 128°.∗

A pharmacodynamic comparison of the compounds mentioned above was made by studying (1) their effect and that of controls on the growth of Lupinus seedlings in plant physiological solutions; (2) their action on the muscular coordination and respiration of goldfish, Carassius auratus; (3) their influence on the behavior of mice, injected intraperitoneally; and (4) of rats, also injected intra peritoneally; (5) their local anesthetic effect on the cornea of the rabbit's eye and on frog-skin; (6) their action on surviving preparations of smooth muscle from the intestine of the cat and uterus of the guinea pig; (7) on the kidney function of rabbits after administration by mouth; (8) on the circulation and respiration of etherized cats after intravenous injection; (9) their antipyretic effect on rabbits and rats; and ascertaining (10) the killing intravenous dose for cats. Most of the results obtained are summarized in Table I.