Some Ethers and Esters of Saligenin. 145 



71 (1818) 



The pharmacological action of some ethers and esters of 



saligenin. 1 



By ARTHUR D. HIRSCHFELDER and HERMAN H. JENSEN. 



[From the Department of Pharmacology, University of Minnesota, 

 Minneapolis, Minn.] 



Benzyl alcohol saligenin and other aromatic alcohols have 

 been shown to possess local anesthetic and antispasmodic action 

 (Macht; Hirschfelder; Hjort). Hirschfelder and Quigley have 

 also demonstrated that the local anesthetic action of benzyl 

 alcohol and its derivatives is diminished when one of the inactive 

 hydrogens {i.e., in the CH 2 of the CH 2 OH carbinol group) is 

 substituted by another radical; or, in other words, that the 

 secondary aromatic alcohols are not as good local anesthetics as 

 the primary, and that substitutions for both the CH 2 hydrogens 

 (tertiary alcohols) causes complete loss of local anesthetic action. 



Although Hirschfelder, Lundholm and Norrgard had demon- 

 strated that methyl and ethyl substitutions on the phenolic 

 hydroxyl of saligenin rendered the substances more irritating than 

 saligenin, a more extensive study of this type of substitution 

 products was desirable, particularly on account of the fact that 

 they furnished some alcohols homologous with acetyl-salicylic 

 acid. 



The substances studied may be devided into three groups: 



I. Ethers of saligenin with substitution on the phenolic hydroxyl: 

 i.e., the ethyl, w-butyl, iso-amyl and benzyl ethers. 



0 



OC2H5 OCH 2 CH 2 CH 2 CH 3 

 CH 2 OH ( /\ CH20H 



1. 11. 



Ethyl saligenin. iV-Butyl saligenin. 



1 The substances used in this research were prepared by Merrill C. Hart as by- 

 products of an investigation of the phenolic alcohols and their derivatives as anti- 

 septics and for the chemotherapy of the venereal diseases, with the aid of funds 

 furnished by the United States Interdepartmental Social Hygiene Board. Their 

 preparation has already been described elsewhere (M. C. Hart and A. D. Hirsch- 

 felder, Jour. Am. Chem. Soc, 1921, July). 



