1869.] 



Action of Hydrochloric Acid on Codeia. 



461 



(which does not contain a replaceable atom of hydrogen) is only isomeric 

 with codeia, and not identical. If, therefore, codeia be morphia where H 

 is replaced by CH 3 , the atom of hydrogen so replaced must be one of those 

 contained in one of the radicals which enter into the composition of mor- 

 phia. Thus — 



Morphia. Methyl-morphia. Codeia. 



C 17 H 17 HNO s C 1T H 17 (CH.) N0 3 C„ H 17 H X0 3 



H H CH 3 



The action of hydrochloric acid on morphia * leads to the elimination of 

 H 2 0, and the formation of a new base, apomorphia, thus — 



Morphia. Apomorphia. 



C„ H 19 N0 3 = H 2 + C 17 H 17 NO a ( 1 ) 



Codeia under the same circumstances might yield a similar base, apo- 

 codeia, thus — 



Codeia. Apocodeia, 



0„ H a N0 3 =H a O + C M H 19 NO, (2) 



Or it might behave like narcotine f , which, under the same conditions, 

 splits up into chloride of methyl and the hydrochlorate of a new base. 



Thus with codeia — 



Codeia, Morphia, 

 O l8 H al N0 3 + HC1= CH 3 CI + C 17 H 18 HN0 3 ; (3) 



but, as has already been shown, if morphia were thus produced, it would 

 be converted, under the circumstances, into water and apomorphia, so that 

 the whole reaction would be — 



Codeia, Apomorphia. 

 C 17 H 17 (CH,) H N0 3 + HC1=CH 3 C1 + H 2 + C 17 H 17 NO, (4) 



In order to examine the nature of the reaction taking place, some codeia 

 (forming part of a supply of 10 oz. given to us by the eminent manufactu- 

 ring chemists, Messrs. M'Farlane, of Edinburgh), was submitted to experi- 

 ment. The substance used when examined for morphia failed to indicate 

 the presence of the smallest trace, was wholly soluble in ether, and, on 

 combustion with oxide of copper and oxygen, after drying at 120°, yielded 

 the following numbers : — 



0*3720 gramme gave 0*9330 carbonic acid and 0*2450 water. 



Calculated. Found. 





216 



72-25 



72-07 



H 21 



21 



7-02 



7*32 



N 



14 



4-68 





o 3 



48 



16-05 





C 18 H 21 N0 3 



299 



100*00 





Codeia was sealed up with from twelve to twenty times its weight of 

 * Proc. Eoy. Soc. vol. xvii. p. 455. t Proc. Koy. Soc. vol. xvii. p. 337. 



