380 MR C. G. WILLIAMS RESEARCHES ON 



ing to Strecker's experiments,* takes up only one equivalent of the alcohol 

 radicals, and is therefore concluded with safety to be a nitryl base. Chinoline 

 affords still more complete evidence of belonging to the same class, for not only 

 is it incapable of taking up more than one equivalent, but, by the operation, it be- 

 comes converted into a fixed alkaloid. Now, any process for making artificial 

 quinine by means of the reactions mentioned above, would result in the forma- 

 tion of an ammonium base, which must of necessity have a totally difi'erent con- 

 stitution to quinine. It may be worth while, for a moment, to glance at the for- 

 midable difficulties by which the artificial formation of such a base as quinine is 

 surrounded. In the first place, in the present state of our information, it appears 

 to consist of three radicals, united and having one equivalent of nitrogen and two 

 of oxygen attached. Now, to acquire a knowledge of the constitution of these 

 three radicals (one of which, in all probability, is oxidized) is a problem involving 

 a new mode of research, the key to which appears, for the present, to be hidden. 

 And even supposing the three radicals known, they have to be formed ; and then 

 to combine them with the addition of an equivalent of nitrogen, without destroy- 

 ing the group, presents a task of no ordinary difficulty. 



I should not have entered upon this branch of the subject, had it not been for 

 the manner in which the possibility of the formation of quinine, by the method 

 above alluded to, has been accepted as a reality, which is the more remarkable 

 from the manner in which Hofmann cautioned chemists against placing too much 

 reliance upon the success of the process. 



As it is my wish to correct, as far as my information will permit me, the 

 erroneous views which have been formed of the relations between chinoline and 

 quinine, I return to the supposed similarity between the action of heat upon qui- 

 nine and the hydrated oxide of tetramethylammonium. This part of the subject 

 is the more interesting, as it appears to have formed one of the links in the chain of 

 reasoning, which led to a belief in the possibility of converting leukol into quinine, 

 by the successive actions of iodide of methyl and oxide of silver. As the fixed 

 base, hydrated oxide of tetramethylammonium, by heating yields trimethylamine, 

 the difference being C 2 H 4 2 , so quinine, less C 2 H 4 2 yields the old formula of 

 leukolf thus, — 



8 H 13 N0 2 --0 2 H 4 0- 3 =C e H 9 K 



Hydrated Oxide Trimetbyl- 



of Tetramethyl- amine, 



ammonium. 



C 20 H 12 NO 2 -C 2 H 4 O 2 = C 18 H 8 N 



Quinine. Leukol. 



The identity in kind of the above equations presupposes two conditions, neither 



* Researches in Organic Chemistry, by Adolph Steecker. Compt. Rend. xxxi. 49. Chem. 

 Soc, Quart. Jour. 1854, vol. vii., p. 278. 



f Quart. Jour. Chem. Soc, vol. iv., p. 328. 



