ADRENALINE (EPINEPHRIN, ADRENINE) 83 



Jowett [1904] arrived at results similar to those of Pauly ; on 

 complete methylation and subsequent oxidation he obtained veratric 

 acid and trimethylamine ; of the above two formulae he favoured the 

 first, subsequently shown to be the correct one. Further investigations 

 were carried out by Abderhalden and Bergell [1904] and by Ber- 

 trand [1904, I, 2]. In the meantime the problem was being attacked 

 in a different way by Stolz whose results, although not published until 

 1904, had already led in August 1903 to a patent application of 

 the Farbw. vorm. Meister, Lucius und Briining [1904] describing 

 the synthesis of a substance of the constitution I (above) which 

 could not at first be obtained crystalline but seemed to be physi- 

 ologically identical with adrenaline. Similar synthetic experi- 

 ments were published somewhat later by Dakin [1905, 1-3], but al- 

 though the identity of the synthetic substance with adrenaline was 

 rendered extremely probable, this identity could not be proved rigor- 

 ously, until the former substance had been crystallised and finally 

 resolved into its optically active components, one of which was found 

 to be completely identical with natural adrenaline (Flacher [1908]). 

 Before this, an independent proof of the constitution of adrenaline had 

 been furnished by Friedmann [1904, 1906] who showed that von 

 Fiirth's tribenzenesulphonyl adrenaline, which is optically active, lost 

 its activity on oxidation to the corresponding keto-derivative, which was 

 crystallised. This proved that adrenaline is a secondary alcohol (for- 

 mula I) and its constitution was further established by a comparison of 

 the above-mentioned ketone with a synthetic specimen obtained from 

 the amino-aceto-catechol of Stolz. 



Nomenclature and Synonyms. 



It is clear from the above that the active principle of the supra-renal gland has re- 

 ceived different names from various investigators. The three principal ones are 

 "epinephrin" (Abel), " suprarenin " (von Fiirth) and "adrenalin" (Takamine), and these 

 are the only ones in scientific use, together with "adrenine" which has lately been em- 

 ployed in the " Journal of Physiology ". On grounds of scientific priority the name should be 

 adopted, which was suggested by the chemist who first isolated the substance in a pure 

 state ; this was Takamine and we therefore use the name adrenalin(e) in the present mono- 

 graph ; this name also happens to be the one at present in most general use. The objection 

 to adrenalin is that it is a proprietary trade-name. For this reason the English Chemical 

 Society used for some time the name epinephrin, which has also been adopted more recently 

 by the American Medical Association. Apart from the fact that Abel first applied this 

 name to an amorphous and probably impure substance there is the additional confusion, 

 that for a long time he designated by it a supposed artificial alkaloidal anhydride of the 

 active principle, which latter he called epinephrin hydrate ( = adrenalin) and some of 

 his papers speak of epinephrin and adrenalin as two distinct substances. Later, when 



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