THE HISTORY OF ADRENALIN 71 



compounds which approach closely the constitution of adrenalin. 

 Bodies such as 



HO HO 



HO ( ) CH(OH) . CH 2 NH 2 and HO^ > CO . CH 2 NH 2 



have an action comparable with that of /3-/-hydroxyphenylethyl- 

 amine. It is remarkable, however, that the diamines have an 

 opposite physiological action to that of the monamines. Thus 

 putrescine, NH 2 CH 2 . CH 2 . CH 2 . CH 2 NH,>, and cadaverine, its 

 next higher homologue, which were the first ptomaines to be 

 identified, cause a fall of blood pressure. 



The researches in the adrenalin series undertaken by Tutin, 

 Caton, and Hann in 1909-10 are typical of much work that has 

 recently been carried out in this connection. Finding the 

 methods previously employed to be inapplicable, /3-/>-dihy- 

 droxy-/3-phenylethylamine 



HO^~ ~\cH(OH)CH 3 NH a 



was prepared from anisole, X., which, with chloroacetylchloride 

 in the presence of excess of aluminium chloride, yielded w-chloro- 

 />-hydroxyacetophenone, XL, the acetyl derivative of which, XII. , 

 was heated with potassium phthalimide, and the resulting 

 />-acetoxy-<w-phthaliminoacetophenone, XIII., converted into the 

 hydrochloride of &)-amino-/-hydroxyacetophenone, XIV., by 

 hydrolysis with concentrated hydrochloric and acetic acids : 



CH3O ( ) + C1CO . CH S C1 -> [CII3O / \ CO . CH 2 C1 ->] 

 f "^CO.CHoCI -> AcO ( ) CO . CH 2 C1 -> 



x. 

 HO 



XI. XII. 



,CO 



AcO f~\ CO . CH 2 N / \ C 6 H 4 -> HO ^ ) CO . CH 2 NH 2 . HC1 



<:0' 

 XIII. xiv. 



The physiological action of the free base was found by Dale 

 to be of the same order as that of the keto-base corresponding 

 to adrenalin, or about one-tenth that of /3-^-hydroxyphenyl- 

 ethylamine. The secondary alcohol, above, co-ordinate with 



