THE HISTORY OF ADRENALIN 69 



of the complexes NH(CH 3 ) and C G H 3 (OH),C, and establishing 

 the structural formula : 



HO 

 HO< >CH(OH).CH 2 .NHCH 3 . 



Adrenalin is soluble with difficulty in cold water, more easily in 

 hot, and dissolves in weak acids with the formation of salts. It 

 acts as a weak alkali to litmus. Alcohol dissolves it slightly. 

 On account of its phenolic nature it is soluble in caustic alkalies. 

 It is readily oxidisable, its aqueous solution rapidly becoming 

 pink and finally brown, and is a strong reducing agent. The 

 quantity of this substance occurring in the adrenal glands of 

 mammals is only a few parts in a thousand. It is one of the 

 most potent drugs. Injection in minute amounts causes an 

 enormous increase in the blood pressure, and acts exactly as 

 extract of the suprarenal glands. Applied externally in aqueous 

 solution to a mucous membrane it causes contraction of the 

 arterioles, and is consequently much used in minor surgery. 



As soon as the constitution of adrenalin had been deter- 

 mined, efforts were made to effect its synthesis. And in 1904 

 Stolz showed how this might be accomplished. In his method 

 catechol, I., is condensed with chloracetic acid, II. : 



HO HO 



HO/" "\ + HOOC . CH 2 C1 -> HO {} CO . CH 2 C1, 



11. in. 



the &>-chloro-;/j/>-dihydroxyacetophenone, III., so produced is 

 acted upon by methylamine, and the resulting methylamino- 

 ketone, IV., converted by reduction with aluminium amalgam 

 into the secondary alcohol V., which is racemic adrenalin : 



HO HO 



HO {J CO . CH 2 C1 + CH 3 NH 2 ' -> HO / J> CO . CH 2 NHCH 3 -» 



in. IV. 



HO 

 HO ^ >CH(OH).CH 2 NHCH 3 . 



v. 



Cushny found that the substance so obtained is physio- 

 logically less active than the natural product, which is the 

 laevorotatory form, and has twelve times the activity of its 



