Abstract
One of the authors reported the remarkable antispasmodic properties of benzyl benzoate and of the benzyl esters for smooth muscle, 1 and the local anesthetic properties of benzyl alcohol. 2 Numerous attempts were made by different investigators to prepare and study analogous benzyl esters and derivatives of benzyl alcohol, with the object of improving the therapeutic value of the original substances. Thus, Hirschfelder 3 pointed out that hydroxy-benzyl alcohol, or saligenin, also produced local anesthesia and was water-soluble. While phenmethylol and saligenin were both potent local anesthetics they had also a mildly relaxant or antispasmodic effect on smooth muscle preparations. Starting with saligenin, we synthesized a series of halogenated and other derivatives, and studied them especially as to their local anesthetic properties and their antispasmodic effects on smooth muscle.
The following compounds were prepared: amido saligenin, nitro saligenin, nitroso saligenin, mono-chlor saligenin, di-chlor saligenin, mono-brom saligenin, di-brom saligenin, mono-iodo saligenin, di-iodo saligenin, chlor-brom saligenin, brom-iodo saligenin, brom-nitro saligenin, nitro saligenin benzoate and saligenin nitro benzoate. All these compounds are solids and the majority are soluble in water only to a limited extent. Di-iodo saligenin is a very poorly soluble substance, saturated solutions of which give concentrations of only 1 : 20,000.
The local anesthetic effects of these compounds were studied on sensory nerve endings of frogs'legs, on the conjunctivae of cats and rabbits and by the wheal method in guinea pigs. Minimal concentrations of the drugs, as well as the duration of the anesthesia, were taken into consideration when comparing the relative efficiency of the different compounds.
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