1889 - 90 .] Mr Dott and Dr Stockman on Morphine. 
323 
morphine in which one hydrogen atom has been replaced by methyl, 
and Grimaux in 1881 succeeded in forming codeine from morphine. 
Beckett and Wright, by acting on codeine with acetic anhydride, 
found that they could only introduce one acetyl group, the other 
hydroxyl hydrogen (of the morphine molecule) having been already 
replaced by methyl. For the same reason, Gerichten found that 
by submitting codeine to the action of phosphorus pentachloride, 
he was able only to replace one hydroxyl by chlorine, the compound 
obtained having the formula C 18 H 20 ClNO 2 (chlorocodide). By 
continued action of the pentachloride, the compound C 18 H 19 C1 2 N0 2 
was obtained, whence it is evident that the third atom of oxygen in 
the morphine molecule does not exist as hydroxyl. 
By oxidation of morphine Chastaing obtained picric acid, proving 
that morphine contains the benzene chain. Wright and Mayer 
obtained pyridine on distilling morphine with potash. By distilla- 
tion with zinc dust Gerichten and Schrotter obtained pyridine, 
phenanthrene, pyrrol, trimethyl-amine, and other compounds. 
Although up to the present time the constitution of morphine has 
not been certainly determined, there is reason to believe that it is 
essentially a phenanthrene derivative, containing alkyl and hydroxyl 
groups. Phenanthrene consists, as it were, of three benzene rings 
welded together, and is represented graphically as follows : — 
HC=CH HC=CH 
HO— C C— CH 
HC=-(JH 
The nitrogen probably replaces one of the CH groups as in pyri- 
dine, and it would appear from the number of hydrogen atoms in 
the morphine molecule that the latter must be a hydro derivative, as 
piperidine is of pyridine. We are aware that it has been recently 
suggested that there are a methyl and an ethyl radical directly com- 
bined with the nitrogen, in which case the nitrogen could not be 
combined as it is in pyridine and chinoline. In view of the fact 
that pyridine has been obtained from morphine, and from the 
