322 Proceedings of Royal Society of Edinburgh. [sess. I 
acid radical, such derivatives being substitution compounds. The 
substitution could not by any means be carried further. That is to 
say, monoacetyl- and diacetyl-morphine were formed, but not the 
triacetyl or any higher derivative. Butyric and benzoic anhydrides 
were tried with precisely similar results. Whence it is manifest 
that the morphine molecule contains two hydroxyl groups, a fact 
which has been confirmed by the experiments of Hesse and of 
Gerichten. On referring to the original paper of Beckett and 
Wright, it will be observed that these chemists adopt the double 
formula C 34 H 38 N 2 0 6 for the molecule of morphine, so that they use 
the terms diacetyl- and tetracetyl-morphine for what we have called 
monoacetyl- and diacetyl-morphine. In a former communication 
to this Society we have fully discussed the objections to the higher 
formula. It seems to be clearly established that the third atom of 
oxygen is either connecting or ketone oxygen, i.e. oxygen which acts 
as the connecting link between two atoms of carbon, or otherwise 
has its combining powers saturated by union with one atom of 
carbon. The next important point to be noticed is that those two 
hydroxyl groups in the morphine molecule have different values — 
fulfil different functions. It had long been known that morphine 
is readily soluble in solutions of the caustic alkalies and in lime 
water, but it was reserved for Chastaing to show that this ready 
solubility is due to the formation of definite compounds with the 
alkalies. These bodies have the general composition M, cwro* 
H 2 0 or M0H,C l7 H 19 N0 3 , where M represents a monatomic metal 
such as sodium. That is to say, that while the morphine molecule 
contains two hydroxyl groups, only one of these is capable of having 
its hydrogen replaced by a metal. In this respect and in some 
others, such as its coloration with ferric salts, morphine resembles 
a phenol. Indeed the readiness with which morphine reacts with 
potash, evolving heat and forming a crystalline compound, is very 
suggestive of phenol (carbolic acid). In the same way that phenol 
(C 6 H 5 OH) forms ethers, as methyl-phenylether (C 6 H 5 O.CH 3 ) so mor- 
phine (C 17 H 18 N0 2 0H) gives us ethers, the morphine-methyl ether 
being codeine (C l7 H 18 N0 2 .0CH 3 ) which is found along with mor- 
phine in opium. By a study of the products of decomposition of 
codeine under different conditions, additional light is thrown on the 
constitution of morphine. Anderson first showed that codeine is 
