TRANSACTIONS OF THE SECTIONS. 89 



codeine is as follows. When dicodeiue is treated with hydrochloric acid, it under- 

 goes the following reaction, 



C_, II,jN, 0,„ 4IIC1+HC1= H, 0+0„II,3 CIN, 0„, 4HC1. 



The resulting chlorinated base is soluble in ether, and gives amorphous salts : hence 

 it cannot be a tetra-base ; and hence it follows that dicodeine has a C^^ formula. 

 When dicodeine itself is similarly treated, the lirst product formed appears to con- 

 tain chlorine and carbon in the ratio of 1 to 3G ; whence codeine itself is a Cgg body. 

 Tetracodeine evidently belongs to the series designated as the "tetra" series; and 

 these have been shown to be C,,^ substances. Hence tetracodeine has double the 

 formula of dicodeine, which is double that of codeine ; whence the names. 



The action of hydrochloric acid on tri- and tetracodeine, however, is quite dif- 

 ferent : in the case of tricodeine, the elements of water are removed, and an 

 "apo" base containing no chlorine at all is formed; tetracodeine, on the other 

 hand, undergoes no change whatever when heated for a long time with hydro- 

 chloric acid. 



The action of hydriodic acid and phosphorus on codeine, dicodeine, and tetra- 

 codeine is again very different, as exemplihed in the following reactions: — > 



Codeine 40 +36HI=8CH3 1+4H, O+I10+ {(M.+IIj,) + 12111-4113 0} 



Dicodeine.... 20,-l-25HI = 8Cn3 1+4H, O+I, + {(M, + HJ + 9III-4H,0} 



Tetracodeine.. U,+18m = 8CH3l+2H, 0+ { M^ +10HI-2H,O} 



With the codeine Hjg is added on to M^ ; with the dicodeine, Hg only ; and with 

 the tetracodeine, no H at all : a tetra-base results in each case. The product from 

 dicodeine has the formula C^^^ 11,53 '^'^a ^20) ^m, which cannot be halved ; the pro- 

 duction of this substance (which is the end product of the reaction) shows again 

 that the tetra-bases do not contain less than (Jjgg. 



When morphine is treated with phosphoric acid at 200°, two products are ob- 

 tained corresponding in properties to dicodeine and tetracodeine ; these are not, 

 however, the morphine polymerides, but are " apo " derivatives therefrom. One is 

 soluble in ether, and forms crystalline salts though amorphous itself; this is pro- 

 duced only in small quantity, and appears to be identical with apomorphine, 

 which is accordingly viewed as a dimorphine derivative — • 



2TI=4H,0+(M,-4II, 0) = 4n,0+C,,H,,N,0,. 

 The other is a tetra-base formed by the reaction 



4M=2H, 0+(M;-2H, 0)=2H, O+C^^ H,,,N, 0,,. 



This latter gives rise to new derivatives when treated with hydrochloric acid or 

 hydriodic acid; it is quite as powerful an emetic as morphine, according to Dr. 

 Stocker's experiments, but does not seem to produce so much after-prostration. 



Most of the above products have not yet received names, on account of their 

 complicated composition ; the term diapotetramorphinc has been given to the last- 

 described base on account of its having the composition of tetramorphine minus 

 two proportions of water, = M^ — 2H„0. Applying the same land of nomenclature 

 to apomorphine, this base should be tQnneiitdrapvdimorphine, having the composi- 

 tion of dimorphine minus four proportions of water, =M., — 4H2 0. 



A large number of other products have also been obtained, and are now in course 

 of examination. It is hoped to extend the investigation of the opium alkaloids to 

 some of the less-known ones, such as narccine and papaverine. In reference to 

 this point the author cannot conclude without acknowledging the extreme kindness 

 and liberality of Messrs. Macfarlane of Edinburgh ; during the course of these re- 

 searches these gentlemen have furnished gratuitously large quantities of several 

 alkaloids, including the rarer ones, and amounting in the aggregate to several 

 pounds weight of materials of the highest degree of purity. Without the help thus 

 liberally bestowed, the investigations would have been impossible. 



