492 Mr. H. D. Dakin. [May 29, 
results which would appear to exclude the second formula and support the 
first. Although criticism must be postponed until further particulars are 
available, still it may be noted that as at least one of the reactions—the 
formation of “ peradrenalon ”—appears to be abnormal, additional experimental 
evidence is very desirable.* 
It is clear that the subject had reached a stage at which synthetical 
methods might be employed with a possible chance of success, and in January, 
1904, I commenced experiments in this direction. A considerable part of 
my work has, however, been anticipated by workers in the laboratory of 
Meister Lucius and Briining (9), and whilst I wish to disclaim any pretensions 
to priority, I take the opportunity of stating that my results were entirely 
independently arrived at, and that, owing to the method of publication 
adopted (Patent Specifications), it is only recently that I have become 
acquainted with the main portions of their work. 
Dziergowski (10) has shown that when catechol is heated with chloracetyl- 
chloride, or with a mixture of chloracetic acid and phosphorus oxychloride, 
chloracetylcatechol is formed. It appeared probable that, by acting upon 
this substance with methylamine and subsequent reduction of theproduct, a 
substance would be produced which should have the formula (I) ascribed to 
adrenalin :— 
HOC + CH,CLOS = HX » _C.CH,Cl+ HCl. 
cee Cl La 
HO 
HO »-C.CH,C1+ 2NH,CH; HO » . C.CH;.NHCH, + NH,CH;HCI. 
== | 
O O 
HO HO 
HO< ». C.CH,.NHCH; + H2 = HX >». CH(OH).CH.NHCH:3. 
I 
O 
This series of reactions has been carried out, and a substance obtained 
which has very many of the physiological and chemical properties which are 
* It may not be out of place to note that the statement made in abstracts of 
Friedmann’s paper in the ‘ Biochemisches Centralblatt’ and elsewhere to the effect that 
adrenalin on oxidation gives adrenalon (methylamino-acetyl-catechol) appear to be 
incorrect. This would obviously be of the utmost importance if true, but Friedmann 
apparently oxidised the benzenesulphonic acid derivative of adrenalin, and obtained a 
substance indistinguishable from the benzenesulphonic acid derivative of adrenalon, 
which is quite a different matter. As the substances are very badly characterised, too 
much weight must not be placed on the result, which might possibly be explained in other 
ways. 
