1872.] 



History of the Opium Alkaloids. 



207 



A. Codeia product, 0*3985 grm. gave 07050 C0 2 and 0*200 H 2 



0-3670 „ 0-2280 Agl. 



B. Morphia product, 0-3190 >> 5635 C0 2 and 01610 H 2 



0-3140 „ 0-5560 C0 2 and 0-1570 H 2 < 

 0-2810 „ 0-1775 Agl. 



Found. 



C 13G H 161 IN 8 O 20 ,8HI 



Calculated. 



A. 



B. 



1632 48-34 



48-25 



48-17 48-29 



169 5-01 



5*55 



5-61 5-55 



1143 33-86 



33-57 



33-77 



112 3-31 







320 9-48 







3376 100-00 







In physical character and chemical deportment the derivatives from 

 morphia obtained as above described are indistinguishable from those of 

 the same composition obtained from codeia. The physiological experi- 

 ments of Mr. Stocker given in the next section show that no particular 

 difference is discernible in this respect also ; hence it is concluded that the 

 codeia products are not merely isomeric, but are identical with the corre- 

 sponding morphia derivatives. 



From the fact that hydriodic acid alone does not eliminate methyl from 

 codeia in the form of methyl iodide, but causes the separation of free 

 iodine, it appears more probable that the formation of the compound 

 C B8 H 82 1 2 N 4 O 10 , 4HI, obtained by the action of hydriodic acid in pre- 

 sence of the phosphorus on codeia, is brought about in accordance with the 

 equations : — 



(1) 4C 18 H 21 NO a + 14HI = 4I 3 + 2H a O + C 7a H 90 1 2 N 4 O 10 , 4HI, 



(2) C 72 H 00 1 2 N, O 10 , 4HI + 4HI = 4CH 3 1 + C 



68 H 82 I 3 N 4 O 10 ,4HI, 



rather than the equations 



(3) C 18 H 21 N0 3 + HI=CH3l + C 17 H 19 N0 3S 



(4) C 17 H 19 N0 3 + 2HI=I a +C i7 H al N0 3 , 



(5) 4C 17 H 21 N0 3 + 6HI = 2H 2 O + C 08 H 82 1 2 N 4 O I0 , 4HI ; 



i. e. that the action does not consist in the production of morphia from 

 codeia and its subsequent alteration by addition of H 2 , polymerization, 

 addition of 2HI, and subtraction of 2H 2 ; but that these alterations take 

 place in the codeia molecule before the elimination of methyl as CH 3 1, this 

 elimination forming the last stage instead of the first. This circumstance 

 may account for the non-production from morphia of compounds belong- 

 ing to the series 4Y + wHI +pTl 2 O, which are formed from codeia when 

 the temperature of the reaction reaches 130°, and under other circum- 

 stances ; for it might naturally be expected that the elimination of tho 



