CHEMISTRY: C. A.' ROUILLER 
145 
ON SOME METALLIC DERIVATIVES OF ETHYL 
THIOGLYCOLLATE^ 
By Charles A. Rouiller 
Pharmacological Laboratory, Johns Hopkins University 
Communicated by J. J. Abel, March 10, 1919 
In 1910 AbeP discovered that thioglycollic ester dissolves antimony tri- 
oxide with the greatest ease, forming an antimony derivative, Sb(SCH2C02 
C2H5)3, according to the equation: 2Sb203+6HSCH2C02C2H5 = 2Sb(SCH2- 
C02C2H5)3+3H20. The antimony compound separates as a heavy oil which, 
when treated in absolute alcohol with ammonia, yields the corresponding 
amide, Sb(SCH2CONH2)3, obtained by precipitation from alcohol with ether 
as a colorless or slightly reddish, semiresinous mass soluble in water in all pro- 
portions with neutral reaction. The expeximents of Rowntree, carried out 
in collaboration with Abel, showed that the new amide is a very powerful 
trypanosomicidal substance. 
Professor Abel found that the thioglycollic ester reacts energetically with 
mercuric oxide also, and in order to determine whether the reaction discovered 
by him is of general applicability, he suggested to the writer that he try the 
action of various other metallic oxides on the ester. It was hoped that the 
resulting products might be so slightly soluble as not to be toxic when applied 
on open wound surfaces, but yet soluble enough to be antiseptic and bacteri- 
cidal. Abel's expectation that his reaction would prove to be general has been 
confirmed; whether the products formed are of pharmacological and thera- 
peutic value we have not yet had an opportunity to determine. 
Following Abel's general method (for details see the forthcoming paper in 
the Journal of the American Chemical Society), the compounds listed below 
have been prepared and analyzed. 
Triethyl bismuthtrithiogly collate, Bi(SCH2C02C2H5)3 
Diethyl mercurydithiogly collate, Hg(SCH2C02C2H5)2 
Ethyl silverthioglycollate, AgSCH2C02C2H5. 
A copper compound with 9.3 % of copper for which no simple formula can 
be derived; the normal compound, Cu(SCH2C02C2H5)2, would contain 21.06% 
of copper. 
Zinc, arsenic, and tin compounds were also prepared but have not yet been 
analyzed. 
^ A more detailed report of this investigation will appear in the May issue of the Journal 
of the American Chemical Society. 
2 Rowntree, L. G., and Abel, J. J., /. Pharmacology Exper. Therapeutics, 2, 1910, (108). 
