
1905. | Substances indirectly Related to Adrenalin. 501 
O O O 
(5 (—on,xi Sy Aen ‘5 OCH 
HO | | | | 
ee yy own Oe 
H H H 
Anilino-acetyleatechol (4). 0-Toluidino-acetylcatechol (4). a-Naphthylamino-acetylcatechol. 
None of these bases produced a decided rise in blood-pressure on injection 
of small quantities. Usually, a fall in pressure was noted, which was least 
marked with the first substance, and was in this case sometimes followed by 
a slight rise. This rise was more marked when the substance obtained by its 
reduction was injected, but even then its activity was far behind the simpler 
alkylamino derivatives. 
As the aromatic bases are only very sparingly soluble in water, they were 
dissolved in weak alcohol for purposes of. injection. Control experiments 
without the bases were made with satisfactory results. The e-naphthylamino- 
acetyleatechol has not been previously described and was prepared by acting 
upon chloracetylcatechol (1 mol.) with a-naphthylamine (2 mols.) and a 
little alcohol. It is a faintly yellowish-green coloured crystalline substance, 
sparingly soluble in dilute spirit and is a very feeble base. 
A base (CgH3(OH):.CO.CH2N H.CH2.CgHs), which may be regarded as inter- 
mediate between the two chemical types already described, was obtained by 
the action of benzylamine upon chloracetyleatechol. The substance is 
crystalline and readily soluble in alcohol. It had very little effect on the 
blood-pressure in rabbits, even when injected in fairly large quantities. 
Another kind of base was prepared by acting upon chloracetylcatechol with 
tertiary bases. For example, aqueous tri-methylamine (1 mol.) was digested 
with chloracetycatechol for some hours, and after adding a drop or two 
of dilute hydrochloric acid the solution was concentrated and crystallised. 
Purification is readily carried out by solution in alcohol and precipitation 
with ether. The substance has the formula CgH3(0H)2.C = O.CH2:N(CHs)3Cl. 
It was found to be more active than the corresponding mono-methylamine 
derivative from which the “ adrenalin-like ” substance was obtained. In the 
ease of rabbits, so small a quantity as 000002 gramme may produce a marked 
rise. In the comparatively few experiments which were made, it appeared 
that the substance was very rapidly destroyed after injection, as when quite 
large quantities were employed the effect was scarcely more prolonged than 
when the minimal amount necessary to produce maximal stimulation was 
used. 
The reduction of the tri-methylamine derivative did not give products of 
