1871.] Hydrobromic Acid on Codeia and its derivatives. 509 



hydrochlorate B and those of a specimen of pure deoxy codeia- salt from 

 codeia (without evolution of methyl bromide), not the slightest difference 

 was discernible between the two ; in their physiological actions, too, as ob- 

 served by Dr. Michael Foster, the two bodies seem perfectly alike, both 

 being utterly dissimilar from apomorphia, from which in all other respects 

 (qualitative reactions, percentage composition, &c.) they differ either not 

 at all or extremely little. 



The portion insoluble in ether of the batch from which hydrochlorate 

 B was obtained was treated with HC1 and fractionally precipitated by 

 strong acid several times successively ; this mode of treatment was adopted 

 rather than that w r ith HBr, as a much larger yield is obtained thus, the 

 hydrochlorates of chlorotetracodeia and chlorotetramorphia being much 

 less soluble in dilute HC1 than the corresponding brominated bodies are in 

 dilute HBr. Finally, nearly white flakes were obtained presenting all the 

 characters of chlorotetramorphia hydrochlorate, and yielding the following 

 numbers after drying at 100°: — 



0-2480 grm. gave 5610 C0 2 and 0*1410 H 2 O. 

 0-1390 grm. gave 0*0755 AgCl. 



Calculated. Found. 



* - s * N 



C 68 816 61*79 61 70 



H 79 79 5-93 6 32 



CL 177-5 13*44 .... 13-45 



N 4 56 4*24 



12 192 14*55 



C 68 H 75 C1N 4 12 , 4HC1 .... 1320-5 100 00 



Hence the portion insoluble in ether must have been bromotetramorphia. 

 The simultaneous formation of bromotetramorphia and deoxymorphia 

 from bromocodide is explainable in two ways : either 



Bromoeodide. Bromotetracodeia. Deoxycodeia. 



(I.) 5C 18 H 20 Br N0 2 + 4H 2 = C 72 H 83 BrN 4 ]2 + C 18 H 21 N0 2 + 4HBr 



Br om otetr acodei a . B r omotetramorpkia . 



(II.) C 72 H 83 BrN 4 O l2 + 4HBr-C C8 H 75 BrN 4 12 + 4CH 3 Br 



Deoxycodeia. Deoxymorphia. 



(III.) C 13 H 21 N0 2 + HBr =C 17 H 19 NO a + CH 3 Br; 

 or 



Bromocodide. Bromomorphide. 



(IV.) C H H 20 BrNO 2 +HBr = C 17 H 18 BrN0 2 + CH 3 Br 



Bromomorphide. Bromotetramorphia, Deoxymorphia. 



(V.) 5C 17 H 18 Br N0 2 + 4H 2 O = C 68 H 73 Br N 4 12 + C 17 H 19 N0 2 + 4HBr. 



Of these two views, the first involves only known substances and reac- 

 tions similar to those already known in the codeia series of derivatives, 



