146 



Scientific Proceedings (119). 



/CH 



OCH 2 CH 2 CH OCH 2 C 6 H 5 

 CH 2 OH CH8 CH 2 OH 



\y \/ 



HI, IV. 



Iso-amyl saligenin. Benzyl saligenin. 



II. Esters of saligenin with substitution on the phenolic hydroxyl 



(acetyl and monobenzoyl saligenin). 



OOCCH3 OOCC 6 H 5 

 Q CH 2 OH Q 



v. VI. 



Acetyl saligenin. Benzoyl saligenin. 



III. An ester with substitution on both hydroxyls (dibenzoyl 



saligenin). 



OOCC 6 H 5 



i /N | CH 2 OOCC 6 H 5 

 \/ 



VI. 



Dibenzoyl saligenin. 



All of these esters and ethers except the dibenzoyl compound 

 are oily liquids, and the latter is a solid; and all are practically 

 insoluble in water but soluble in the usual organic solvents and in 

 olive oil. Their pharmacological properties were therefore studied 

 by dissolving the substances in olive oil and emulsifying this with 

 acacia by the Continental method. 



Toxicity tests, made by determining the dose which was lethal 

 for frogs in twenty-four hours, gave the following results: For 

 the ethers, ethyl saligenin 0.5 mg. per gram frog, w-butyl 0.25 

 mg., iso-amyl 0.12, benzyl 0.36 to 4 mg. ; for the esters, 

 acetyl saligenin 0.9 mg., benzoyl 1.0 mg., dibenzoyl 2.0 to 3.0 mg. 

 All of these compounds are therefore more toxic than saligenin 

 itself. 



The local anesthetic action was tested by dipping the frog's 

 foot into the emulsion and then into one per cent, sulphuric acid. 

 Two per cent, emulsions were used. Anesthetic action set in 

 from two to five minutes after exposure to the drug and lasted 



