CHEMISTRY OF EPINEPHRINE 75 



compound "adrenalin," the name recognized officially in the 

 British Empire and European countries and used extensively 

 in the United States despite the official preference for the term 

 "epinephrine." "Suprarenin," another commonly used term 

 for this compound, was introduced by von Furth 208 who pre- 

 pared insoluble metallic salts of the active principle but failed 

 to isolate the free base in pure form. 



The correct empirical formula of epinephrine (C 9 Hi 3 3 N) 

 was first derived by Aldrich. 9 The existence of a catechol 

 nucleus 



OH 



(T 



in this compound was suggested by the green coloration given 

 when epinephrine is treated with ferric chloride. This color 

 reaction is common to catechol and its derivatives. Takamine 9 

 showed that fusion of epinephrine with KOH yielded proto- 

 catechuic acid. 



OH 

 tf)H 



COOH 



More direct evidence of the position of the side chain of the 

 catechol nucleus was given by Jowett 342 who methylated the 

 hydroxy groupings in the benzene ring of epinephrine (to pro- 

 tect the aromatic radical) and on oxidation of the resulting 

 methyl ether obtained the dimethyl ester of veratic acid. 



OCH 3 

 PCH 3 



COOH 



This reaction showed the position of the side chain relative to 

 the hydroxyl groupings in the epinephrine molecule. The fact 



