88 REPOKT— 1872. 



themselves have not yet beeu isolated, nor have trimorphine derivatives been ob- 

 tained as yet with certainty ; but tetramoi-phine and probably dimorphine deriva- 

 tives have been obtained : some of these are formed by the removal of the elements 

 of water from tlie polymerides themselves, thus constituting " apo- " or anhydro- 

 bodies. It appears probable that apomorphine, the earliest known derivative (ob- 

 tained some years ago by the late Dr. A. Matthiessen and the author), is really a 

 derivative of dimorphine, 



Wheii hydriodic acid and phosphorus act on codeine, hydrogen is added on, 

 methyl is eliminated as iodide, and polymerization is brought about, one or other of 

 a series of substances being obtained, all denoted by the general formula 



by prolonging the action, substances are obtainable of the general formula 



When morphine is subjected to the same treatment, products are found which 

 are apparently absolutely identical with the corresponding codeine products ; 

 much fewer derivatives, however, are obtainable from morphine, the fact of there 

 being no methyl to eliminate and thus place the substance in a quasi-nascent con- 

 dition, being probably the reason for this diflerence : thus all the morphine deriva- 

 tives hitherto obtained by these means belong to the first of the above two series. 



Although most of the substances hitherto examined have energetic physiological 

 actions, allthese derivatives, whether from codeine or morphine, are, compfiratively 

 spealdng,_ inert, doses up to eight grains (0-5 grni.) being given to an adult she 

 terrier witliout producing any symptom more marlied than a peculiar land of 

 diarrhoea, lasting for a few hours. 



_ These results, together with those formerly obtained, indicate that codeine is a 

 kind of methylic ether of morphine, their relative formula being 



_It is noteworthy that both from codeine and from morphine the same compound 

 (M,+IIjJ + 9HI - 4H, O, is derivable. The formula of this substance, ' 



c,3„n,„,iN,o,„,8ni, 



is incapable of being halved, and indicates that these iodized bases are really C,,^ 

 compounds, and not C^.^ bodies as at first supposed. On account of the similarity m 

 properties between these iodized derivatives and the chlorotetracodeine, bronio- 

 tetramorphine, Szc. obtained by the action of hydrobromic acid on codeine, the 

 formulas of these latter are also considered to be double of tliose formerly attri- 

 buted to them ; i.e. they are viewed as C,,ii-C,3c compounds, and not O.^-C,^ 

 bodies. Inasmuch, however, as they still contain four times as much carbon as 

 the original codeine and morphine (these bases being doubled in formula, as above 

 mentioned), the old names are still applicable ; and this class of bodies, which are 

 specially distinguished by being amorjjhous and insoluble in ether, may be con- 

 veniently alluded to as the " tetra-hases." 



To obtain the polymerides of codeine themselves without further alteration by 

 secondary reactions, the action of acids other than hydracids was examined. Phos- 

 phoric acid at 200° (the aqueous solution of codeine" in excess of glacial acid being 

 gently boiled down) yields dicodeine, soluble in ether, amoiphous, but forming 

 crystalline salts — and ietraaxhinc, much resembling in properties all the other 

 " tetra-bases " examined, being insoluble in ether and amorphous, and forming 

 amorphous salts. These two bases appear to be identical respectively with the 

 "isomer of codeine" of Armstrong and the "amorphous codeine" of Anderson, 

 both prepared by the action of sulphuric acid on codeine. On examining this reac- 

 tion a third polymeride was also found to be formed : this is amorphous and soluble 

 in ether, but forms amorphous salts; on account of its being in many respects in- 

 termediate between dicodeine and tetracodeine, it is considered to be tricotleine. 

 This base is not produced by the action of sulphuric acid on dicodeine ; this action, 

 however, gives rise to tetracodeine in quantit3^ 



The proof of the correctness of tho formulae attributed to dicodeine and tetra- 



