491 
The Synthesis of a Substance allied to Adrenalin. 
By H. D. Dakin. 
(Communicated by Professor E. H. Starling, F.R.S.. Received May 29,—Read 
June 8, 1905.) 
(From the Laboratory of Pathological Chemistry, Lister Institute of Preventive 
Medicine.) 
The isolation of adrenalin from the suprarenal gland by Takamine (1) 
and by Aldrich(2) in 1901 has led to a considerable amount of work on the 
chemical nature of this remarkable substance. It is, however, only within 
the last two years that satisfactory elementary analyses and molecular weight 
determinations have been made, and the exact structural formula is still 
unsettled. 
Two formule have been proposed, either of which will account for most 
of the observed facts concerning the chemical behaviour of adrenalin, although 
there are other possible structures which may demand consideration.* 
OH OH 
OH ou 
| | 
CH(OH) CH.NHCH, 
| | 
CH,.NH.CH, CH,OH 
1. IL. 
A preliminary note has been published by Friedmann (5), which contains 
* It is not proposed to give a résumé of previous work, but the following indisputable 
facts upon which speculations as to structure are based may be briefly stated—there is, 
however, much evidence of a less direct nature which will be found in the papers by 
Abel (3), von Fiirth (4), Friedmann (5), Jowett (6), Pauly (7), and Stolz (8). 
(a) Adrenalin, on fusion with alkali, gives catechol, so that an ortho-substituted 
benzene nucleus is present in the molecule. 
(6) Adrenalin, on methylation and subsequent oxidation, gives veratric acid— 
nN 
3°4 dimethoxybenzoic acid—pointing to the existence of the grouping —0¢ > HE o€ ; 
and since further adrenalin gives the colour reactions (FeCl, etc.) of an ortho-dihydric 
phenol, it is concluded that two hydroxyl groups are present in the ring 
HO Me 
HOCH OC, 
Te ee 
(c) On warming with aqueous alkali, methylamine is formed, so that the grouping, 
—NH.CHs is present. 
(d) Adrenalin is optically active, and therefore contains an asymmetric carbon atom 
which will be situated in the side-chain. 
