208 



Dr. C. R. A. Wright's Contributions to the [Mar. 14, 



methyl group would place a portion of the molecule in a quasi-nascent 

 condition, thereby rendering further changes more easy. 



The foregoing experiments, taken into consideration together with those 

 formerly obtained in conjunction with the late Dr. Matthiessen*, lead to 

 several noteworthy conclusions and speculations. 



(1) The actions of hydrochloric, hydrobromic, and hydriodic acids on 

 morphia and codeia are not precisely analogous ; thus the action of HOI 

 appears to give rise more especially to products derived from non-polyme- 

 rized bases; e. g. 3 chlorocodide, which regenerates ordinary codeia by the 

 action of waterf . By the action of HBr, codeia yields not only bases 

 apparently formed from non-polymerized codeia (bromocodide, deoxy- 

 codeia, deoxymorphia), but also bases derived from polymerized codeia 

 and accordingly containing at least C 72 , and probably C U4 (chloro- and 

 bromotetracodeia) . Hydriodic acid, on the other hand, yields no body 

 whose formula can be written as containing less carbon than C 34 ; and from 

 the physical characters of the first products of the action and the constitu- 

 tion of their derivatives (many of which contain at least C 68 and some ap- 

 parently C 13fl ), this proportion of carbon must certainly be doubled and 

 probably quadrupled. 



Hence HC1 yields single-molecule derivatives chiefly ; HBr yields 

 single-molecule derivatives, and also polymeride derivatives, the polyme- 

 rides containing at least C 68 or C 72 (possibly the formulae attributed to 

 bromotetracodeia and analogous bases may require doubling, as the phy- 

 sical character of the bases and their salts indicate that they belong to the 

 same rank as the iodine derivatives); HI yields polymeride derivatives only. 



(2) It being assumed that the molecules of codeia and morphia contain 

 respectively either C J8 and C 17 or C 36 and C 34 (which latter is probably the 

 case, experiments now in progress indicating that the molecular formulae 

 of these bases are double those usually ascribed to them), the above expe- 

 riments lead to the conclusion that there exist polymerides of these alka- 

 loids containing C 72 , C 144 , , or C 68 , C 136 , , these polymerides 



being formed by the action of strong acids, and serving as starting-points 

 for new series of derivatives. Experiments to obtain these polymerides in 

 an unaltered condition are, as has been previously stated, in progress, and 

 apparently with success. 



This facile disposition to form polymerides is not an unknown feature in 

 alkaloids, the experiments of Anderson having shown that the pyridine 

 bases are characterized by this property. This fact would appear to warrant 

 the speculation that morphia and codeia contain carbon groups analogous 



* Matthiessen and Wright, Proc. Koy. Soc. vol. xvii. pp. 455, 460 ; and vol. xviii. 

 p. 83. 



f Experiments are in progress which appear to show that the action of HC1 on both 

 codeia and morphia is canable of giving rise, when pushed to an extreme, of bases inso- 

 luble in ether, and of characters similar to chloro- and bromo-tetracodeia, with less ease, 

 however, than HBr. 



