230 SCIENCE PROGRESS 



pressure. The chief use of the substance is in minor surgery : 

 when a solution is applied externally to a mucous membrane, 

 contraction of the arterioles takes place : adrenaline is there- 

 fore an excellent styptic. This local action is only exhibited 

 by two or three of its nearest chemical allies, not being 

 shown, for instance, by />-hydroxyphenylethylamine. 



When the constitution of adrenaline was determined, attempts 

 were made to prepare the substance artificially. The first 

 synthesis was effected by Stolz (Ber. 1904, 37, 4149); the base 

 is now manufactured by his method by the Farbwerke vorm. 

 Meister, Lucius & Bruning under the name of suprarenin 

 (German patents Nos. 1528 14 and 157300). 



The synthesis involves the following changes : Catechol 

 (I.) having been condensed with chloracetic acid (II.) — 



II. III. 



HO 



HOr^ 



+ HOOC . CH 2 C1 



K^ 



CO . CHXI 



IV. V. 



HO HO 



HOi^N HO f^ 



l v JcO.CH 2 .NH.CH, -> L v> JcHOH.CH 2 .NHCH, 



the chloroketone (III.) that is produced is acted upon by methyl- 

 amine and converted into a methylaminoketone (IV.) ; and this 

 is converted by reduction into the corresponding secondary 

 alcohol (V.) which is racemic adrenaline. 



It was found by Cushny, whose observations have been con- 

 firmed by Abderhalden and Miiller, that the racemic substance 

 obtained in the way described is physiologically less active 

 than the natural lasvorotatory substance, the reason being that 

 the d-form has only about T V to T * T of the activity of the /-form. 1 

 This inferior activity of the racemic form might be readily 

 overcome by using more concentrated solutions but the German 

 manufacturers have preferred to resolve their racemic product 

 by means of its acid tartrate (Flacher, Zeitsch. physiol. Client. 

 1908, 58, 189). 



Various other syntheses of the substance have been carried 



1 A considerable difference in physiological activity between optical antipodes 

 has also been found by Cushny in the case of the alkaloids hyoscyamine and 

 hyoscine. These observations suggest that there must be a chemical combination 

 between the drug and the asymmetric protoplasm of the cell. 



