370 DR ANDERSON’S RESEARCHES ON SOME OF THE 
obtained ; and as these changes are obviously not confined to the non-nitrogenous 
component of narcotine, but extend to the cotarnine also, I proceeded to the 
examination of the action of nitric acid upon that substance in a pure, or at least 
in a nearly pure, state. 
The products of the action of nitric acid on cotarnine are extremely complex, 
and several different actions appear to occur simultancously, in each of which a 
different decomposition is produced. When concentrated nitric acid is employed, 
an extremely violent and tumultuous action takes place on boiling, and the fluid 
contains a large quantity of oxalic acid. When, however, the acid is more dilute, 
the action goes on more steadily, red fumes are abundantly developed and an 
acid substance is produced, which remains in solution in the nitric acid. The 
preparation of this substance is a matter of considerable nicety, and it is particu- 
larly important that the nitric acid be not employed in too large an excess, partly 
on account of the risk of carrying the action too far, and partly on account of the 
difficulty of separating the product from a very large excess of acid. As the new 
product is liable to undergo a further oxidation with production of oxalic acid, it 
is not safe to attempt its separation by evaporating the nitric acid solution. The 
best method is to dissolve the cotarnine in nitric acid diluted with about twice 
its bulk of water, and then adding strong nitric acid to raise the mixture to the 
boiling-point. Red fumes are copiously evolved, and after some time a small 
quantity of the fluid is taken out and mixed with a considerable quantity of alco- 
hol and ether. If on standing for a short time crystals are deposited, the whole 
fluid is treated in the same manner; but, if they do not appear, the digestion is 
continued somewhat longer, and it is tried again, and so on, until the right point 
is hit. The fluid, mixed with alcohol and ether, is allowed to stand for twenty- 
four hours, and the precipitated crystals are separated by filtration. This sub- 
stance agrees in all respects with the apophyllic acid obtained by WouLER as a 
product of the action of bichloride of platinum upon cotarnine, and which he 
obtained in too small a quantity for examination and analysis. 
Apophyllic Acid—The crude crystals of the acid deposited from the alcohol 
and ether are purified by solution in boiling water, and, if necessary, by digestion 
with animal charcoal and crystallisation. It then presents aJl the characters at- 
tributed to it by WouLeER, and is obtained with ease, either in hydrated or anhy- 
drous crystals, as described by him. It dissolves in water, but not in alcohol and 
ether. Concentrated sulphuric acid dissolves it readily, and the solution remains 
colourless even when pretty strongly heated. Strong nitric acid oxidises it. When 
heated on the platinum knife it fuses, and, on cooling, solidifies into a crystalline 
mass. Its fusing point is 401°. It dissolves in large quantity in potass and soda, 
also in ammonia, and the latter solution, on evaporation, gives very soluble crys- 
tals of an ammonia salt. Its salts are all very soluble, and are not easily obtained 
in a satisfactory state for analysis. 

