194 THE DUCTLESS GLANDS 



be a monobenzoyl-suprarenin (C 6 H 5 CO) C 10 H 10 N0 3 ; to sup- 

 rarenin itself must then be allotted the formula CloHnNOg. 



The next important step was the production of the active 

 substance in a crystalline form. This was effected by Taka- 

 mine and Aldrich independently. The method in both cases 

 was the same. Very concentrated adrenal extracts were 

 largely freed from inactive substances by treatment with 

 alcohol, lead acetate, etc. ; then the active substance was 

 precipitated in the form of microscopic crystals by the addition 

 of concentrated ammonia. The precipitate was then purified 

 by repeatedly dissolving in acid and reprecipitating with 

 ammonia. The resulting prismatic needles or rhombic plates 

 were those of the purified and isolated active principle 

 adrenalin. 



According to v. Fiirth, a careful comparison of the com- 

 position and physiological action of adrenalin with those of 

 his suprarenin indicates that they are one and the same sub- 

 stance. He has decomposed the " suprarenin " iron com- 

 pound with sulphuric acid and thereby obtained "adrenalin" 

 in crystalline form. 



All the authors quoted have obtained different analytical 

 results and suggested different formulae. Aldrich suggested 

 from his analyses the formula C 9 H 13 N0 3 , Takamine 

 C 10 H 15 N0 3 , and Abel C 10 H 18 N0 3 + |H 2 0. The empirical 

 formula of Aldrich is now generally accepted, and from the 

 combined researches of v. Fiirth, Jowett and Pauly, the con- 

 stitutional formula is regarded as 

 OH 



. CH (OH) . CH 2 . NHCH 3 



That is to say, adrenalin is therefore ortho-dioxyphenyl- 

 ethanol-methylamine and is related to tyrosin p-oxyphenyl- 

 amino-proprionic acid. 



If adrenalin be oxidized, we get a substance having the 



formula : 



HO 



\ 



S 



C . CH . NHCH 3 . 



| 

 o 



This substance, adrenalon (methyl-aminoacetylpyrocatechin) 

 has been prepared synthetically by Friedmann, Stolz, and 



