392 
DR. A. W. HOFMANN’S RESEARCHES INTO THE 
The preceding researches show that the action of the bromides and iodides of the 
alcohol-radicals upon ammonia, gives rise to the formation of not less than four 
distinct groups of organic bases. Of these, the members of three groups, correspond- 
ing to ammonia (H3 N), are volatile, while those of the fourth, corresponding to 
oxide of ammonium (H4 N O), cannot be volatilized without decomposition. The 
facility with which the members of this last class arise from those of the preceding 
ones, and the readiness with which their reconversion is effected, renders the former 
group as it were the connecting link between the volatile and the non-volatile organic 
alkaloids. 1 am inclined to attach some importance to the latter point ; for the ac- 
quisition of a general method, by means of which we may rise from the volatile to 
the non-volatile bases, is not unlikely to pave the way to the artificial production of 
the fixed native alkaloids, whose constitution is still shrouded in darkness. We may 
here remember that a very considerable number of these fixed native alkaloids yield 
volatile organic bases when submitted to the action of heat or of potassa, — that is 
under precisely those conditions under which the new ammonium-compounds, which I 
have described in this paper, are converted into conjugate ammonias. Thus quinine, 
cinchonine, strychnine, and pelosine yield among their products of decomposition 
leucoline (chinoline), while piperine gives picoline (?), and morphine, caffeine, co- 
deine and narcotine have actually been converted into alcohol-bases, the former 
yielding methylamine, the latter two propylamine*. 
I readily admit that those processes are by no means so simple as the passage of 
oxide of tetrethylammonium into triethylamine, several processes of transformation 
being in most of these cases accomplished side by side. A certain analogy, however, 
cannot possibly be denied, although, on account of the more complicated formulae of 
the native bases, it cannot as yet be traced in simple equations. In some instances 
the connection even now appears almost palpable. If we compare the formulae of 
quinine and of leucoline, the volatile base derived from its destruction, we are surprised 
to find that these substances exhibit the same elementary difference which we ob- 
serve between oxide of tetramethylammonium and methylamine. 
* M. Werthkim, the discoverer of this base, believes that it stands to the unknown propyl-alcohol in the 
same relation which exists between methylamine, ethylamine and amylamine on the one hand, and methylic, 
etbylic and amylic alcohol on the other. It deserves, however, to be noticed that the formula Cg Hg N for 
this compound, as determined by experiment, expresses not only propylamine but also trimethylamine and even 
methylethylamine, 
r H . r H 
CgHgN=- H N= C,H3 N= C.Hg 
ICg ICj H3J Ic, H5 
In the absence of decisive reactions, it remains doubtful which of these formulae represents the base obtained 
by the action of soda-lime on narcotine ; I may state here that propylamine, as prepared by Wertheim’s process, 
and the liquid containing trimethylamine, for as yet I have not obtained this substance perfectly pure, exhibit 
the same remarkable fishy odour. It deserves moreover to be remarked that Dr. Anderson found that propyl- 
amine occurs, associated with methylamine, among the basic products of the decomposition of codeine. 
