68 REPORT — 1873. 



The action of hydrochloric acid on codeine is in some respects analogous to, in 

 others different from, that on morphine ; the first products formed are derived 

 from non-polymerized codeine, and are (C+HCl) and (C + 2HCI-2H2O), the 

 latter beino- the " chlorocodide " of Matthiessen and the author. As " ehlorocodide " 

 reo-enerates ordinary codeine by the_action of water in sealed tubes, the production 

 of this base, preceded by that of (C+HCl), proves, first, that these substances 

 (and hence by anal c 

 mono-sei-ies, and, se 



(as usually supposed) . . 



mononiorphine is G^^ Hg^ N^ 0^, and not C,, H^ NOg); 



In just the same way the first action of hydrobromic acid on codeine is found to 

 give rise to (C + IlBr), (C-|-2HBr— 2H,0) or " bromocodide " being subsequently 

 produced. 



The further action of hydrochloric acid on " chlorocodide " has been shown by 

 Matthiessen and the author to consist in the elimination of methyl as chloride, and 

 the abstraction of the elements of water, forming " apomorphine," the reaction 

 taking place at 140-150° in sealed tubes. When the action is allowed to take place 

 at 100° however, it follows a slightly different course ; methyl chloride is formed 

 and water is eliminated, but the resulting substance is not " apomorphine," but a 

 bodv which may be regarded as standing intermediate between dimorphine and 

 "apomorphine" (tetrapodimorphine); its physical characters are those of a di- 

 derivative, and it much resembles apomoiiihine in all respects save composition and 

 physiological action ; the recrystallized pure hydrochloride gave numbers leading 

 to the formula (Mg— 2H2 O), "apomorphine" being (Mj - 4H2O) ; and hence the name 

 cliapodimm-pkine is given to this substance. Simultaneously with diapodimorphine, 

 abase isomeric therewith, but belonging to the teti-a-series, is produced ; this, being 

 indicated by the formula (51^—411; O), may be termed tetrapoMvamorpUne. 



The alteration in the physiological action (on cats) of the nioi-phine polymerides 

 produced by successive abstraction of the elements of water is well exemplified by 

 the following Table. The last-mentioned base, odapotetramorphinc, is obtained as 

 the final product of the joint action of concentrated zinc chloride and hydrochloric 

 acid on morphine; its formauon is preceded by that of "apomoi-phine," the base 

 (M+HCl— 1L,0), and a tetra-base (M.j-|-IICl-4H2 0), the one or the other being 

 formed according to the temperature employed and otlier circumstances. 



Di-Scries. 

 Name of base. Relation to morphine. Physiological action. Observer. 



Dimorphine (hypothetical) . . M^ ? ? 



( Produces profuse 1 



Diapodimorphine M^— 2H2O \ salivation but no I Dr. J. G. Blackley, 



( vomiting (cats). ) 



! Moderately pow-1 

 erfulemetic(cats). [ Drs. Gee and 

 Veiy powerful f Stocker. 

 emetic (man). j 



TetraSeries. 



Tetramoi-phine M, { ^e^jJ^tiP^^at J'.'^ f ^^- St°'=^^^''- 



Diapotetramorphine M,-2H,0 j (cXandXgs)!" ( " 



I Produces profuse 1 



Tetrapotetramorphine Mj— 4H2O \ salivation but no I Dr. Blackley. 



( vomiting (cats)i 1 



I Produces neither) 

 salivation nor \ „ 



vomiting (cats). ) 



