CHEMISTRY: C. A. ROUILLER 
465 
and the remarkably concordant results of all his determinations seem 
to establish beyond doubt that its composition is represented by the 
formula C3H4ON2.AuCl3.HCl. The free base itself could not be isolated 
and all the evidence tends to show that it decomposes as soon as it is 
set free from its salts; when any of the latter are treated with alkaline 
reagents (even such weakly basic ones as calcium carbonate or acetate) 
a characteristic, unpleasant, coniine-piperidine-like odor develops and 
vapors which turn moist litmus paper blue are evolved; among the 
products formed when the gold salt is boiled with sodium hydroxide 
solution were identified ammonia, methylamine and methylhydrazine. 
Since the base must be formed by the action of the nitric acid on the 
side chain CH3NHCH2CH(OH) — of the epinephrine molecule, it seemed 
possible that it might also be abtained by treating methylaminoacetalde- 
hyde, CH3NHCH2CHO, with nitric acid. Accordingly, methylamino- 
acetal, CH3NHCH2CH(OC2H5)2, was prepared by heating under 
pressure chloroacetal, C1CH2CH(0C2H5)2, with an aqueous solution of 
one equivalent of sodium hydroxide saturated with methylamine, and 
was converted into the aldehyde by letting it stand overnight in con- 
centrated hydrochloric acid; the solution was then concentrated in 
vacuo at 40° and finally at room temperature over sulphuric acid and 
solid sodium hydroxide. When the resulting syrup was treated with 
nitric acid there was obtained a substance agreeing in all respects with 
that described by Abel. It can also be prepared by treating the acetal 
directly with nitric acid, but in that case the reaction is very violent 
and even after it has apparently ceased sometimes starts again explosively 
and the whole product may be converted into a red tar. The synthetic 
base reduces ammoniacal silver nitrate and Fehling's solutions, evolves 
the characteristic coniine-piperidine odor with alkalies and gives with 
gold chloride a salt difficulty soluble in water and separating from acetone 
containing a little alcohol in beautiful yellow prisms containing the same 
percentages of gold and chlorine as Abel's salt. 
0.2484 g. salt decomposed with 10% aqueous Na202 gave 0.1156 g. metallic Au and 
the filtrate gave 0.3370 g. AgCl. 
When the gold salt is treated with sodium hydroxide solution and 
the mixture is distilled to a small volume the distillate is found to reduce 
Fehling's solution strongly, and the residue in the distilling flask, after 
being filtered from the gold and acidified with acetic acid, gives with 
Found 
Calculated for 
C8H4ON2.AuCI3.HCl 
Au 
CI. 
46.54 
33.56 
46.49 
33.44 
