May 4, 1872.] 
THE PHARMACEUTICAL JOURNAL AND TRANSACTIONS. 
885 
^h I7 no 
Codeia. 
OH 
O.CH, 
Cl 
GVH 
irNO { 
Chlorocodide. 
Cl 
O.CHg 
+HC1=C 17 H 17 N0 | o.CH 3 +H - 0> 
Chloi-ocodide. 
= cl t } +c 17 h 1? no { 0 ", 
Apomorphia. 
CH-, 
C i; H 17 N0 { gg =H j O+C 17 H 1 .NO | 0*. 
Morphia. Apomorphia. 
According to this view morphia should contain two hy¬ 
droxyl groups for every C 17 , and codeia only one. Experi¬ 
ments arc contemplated, with reference to this point, on 
the action of aniline, acetyl chloride, and glacial acetic 
acid, on these alkaloids, whereby it is hoped that 
definite information may be gained as to the presence, or 
otherwise, and the number of the groups CHO (alde¬ 
hyde group), OH, etc. 
(o.) It appears not improbable that codeia and mor¬ 
phia may contain in their molecules benzene residues. 
Schiff has pointed out* that phenols give colourations 
with ferric chloride, whereas the corresponding ethers 
or anisols do not do so ; the well-known distinction 
between morphia and codeia in this respect, therefore, 
gives some support to the idea that both may be benzene 
derivatives. 
III. On the Physiological Action of some of the foregoing 
Derivatives. By Reginald Stocker, M.B., Patholo¬ 
gist in St. Mary’s Hospital Medical School. 
Doses of one decigramme of the compound 
from codeia, and of the similar compound from morphia, 
were given to an adult terrier by the mouth without pro¬ 
ducing any perceptible effect whatever; when the dose 
was increased to three decigrammes, in each case repeated 
defecation in the course of a few hours was produced, the 
stools being more loose than ordinarily and frequently of a 
dark greenish colour ; no other symptom was noticeable, 
and no appreciable difference in the action of the two 
compounds was perceptible. 
Doses of 5 decigrammes of the compound 
^63 82 ^ 2 ^ 4 ^ 10 - 4 HI 
from each of these sources were given to the same dog 
by the mouth with the result of producing similar repeated 
defalcation in the course of two or three hours ; the sole 
difference discernible between these and the former experi¬ 
ments being that the effect was produced somewhat sooner 
and was of longer continuance in the latter cases, a result 
probably produced solely by the larger dose. No material 
differences were observed between the codeia and morphia 
derivative. 
The same dog was employed throughout, two or three 
days being allowed to intervene between each experi¬ 
ment, so that the animal had recovered from the effects 
of a former dose before the administration of another. 
It would hence appear that the derivatives of poly¬ 
merized C 17 H 21 N0 3 are less active than those of poly¬ 
merized Cj-HjgNOg; and also that there is no reason for 
considering the derivatives from codeia as different from 
those of morphia, the corresponding bodies having 
respectively the same quantitative composition and the 
same physical, chemical, and physiological properties. 
codeia and morphia are really double of those formerly 
ascribed to these bases, i.e., are 
^ 36 ^ 42 -^ 2^6 an 4 ^ 34 ^ 38 -^ 2^6 
respectively, the proof of which is (as will be shown in 
a subsequent communication) that the first products of 
the action of hydrochloric acid on these bases appear 
to contain chlorine and carbon in the proportions C 3rt 
and Cl, C 34 and Cl respectively, instead of C ls and Cl, or 
C 17 and Cl. It might bo anticipated, therefore, that 
intermediate polymerides might be formed containing 
respectively, 
N,0, 
Codeia Series. 
C 30 H 42 N I O a Monocodeia. 
C 73 H 84 N 4 0 12 Dicodeia. 
C io8lIi2o N o ( 3i8 Tricodeia. 
Tetracodeia 
Part V. 
I. On the Polymerides of Codeia. 
In Part IV. of these researches reasons have been 
adduced for the following general conclusions, viz., that 
codeia and morphia are capable of forming polymerides 
(with the elimination of methyl in the case of codeia 
in some instances), which yield derivatives containing 
certainly not less than C cs , and probably not less than 
C 13 ~ (C 72 and C 144 in the case of those codeia derivatives 
where methyl has not been eliminated). Experiments 
now in progress tend to show that the formulas of 
Morphia Series. 
Monomorphia... C 34 H 38 ... a w 0 
Dimorphia . C R8 II 70 N 4 0 4 
Trimorphia. C 102 H 104 N„O x 
Tetramorphia... C 13s H 132 N 8 0 2 , 
In the case of codeia these anticipations have been 
verified. 
In order to obtain these supposed polymerides before 
their further alteration by secondary reactions, the 
action of acids other than the hydracids was examined. 
Acetic acid seemed a probable agent for this purpose ; 
but no appreciable quantity of anything different from 
ordinary codeia was obtained after sixty-four hours’ 
digestion at 100° of one part of this base with three 
parts of glacial acetic acid. On precipitation of the 
product by Na 2 C0 3 in large excess, extraction with 
ether, and agitation of the ethereal extract with HC1, 
a crystalline mass was obtained which developed a smell 
of acetic acid on standing in contact with a slight excess 
of HC1; but on analysis this gave numbers agreeing 
with those required for codeia hydrochlorate, and from 
it nothing different from codeia could be obtained; 
probably, therefoi-e, only a trace of acetyl-codeia was 
formed. 
The action of phosphoric acid, however, was found to 
lead to the desired result without the formation of by¬ 
products beyond colouring-matters formed by the high 
temperature employed; by heating codeia with three 
parts glacial phosphoric acid and 5 of water for several 
hours at 100°, no perceptible change is produced. The 
same result follows on boiling for twelve hours (boiling- 
point 105°) with an inverted condenser attached to 
prevent loss of water by evaporation ; but if the boil¬ 
ing-point be allowed to rise slowly from evaporation, 
the mixture being very gently boiled in a long-necked 
flask, the product gradually acquires the power of giving 
an immediate amorphous precipitate with Na 2 C0 3 ; no 
large amount of new substances are, however, formed 
until the boiling-point has risen to about 200°, beyond 
which point the evaporation cannot safely bo pushed. 
The viscid chestnut-coloured liquid, while still hot, is 
dissolved in boiling water and allowed to cool; nothing- 
separates on cooling; when cold, the liquid is nearly- 
neutralized by caustic soda, and then precipitated with 
Na.,C0 3 ; the precipitate is collected on filters, drained 
from mother-liquors, dissolved in weak IIC1, and re¬ 
precipitated by Na 2 C0 3 , to get rid of traces of unaltered 
codeia mechanically retained ; finally, the drained pre¬ 
cipitate is exhausted with ether. The ethereal solution 
yields on agitation with HC1 a crystalline hydrochlorate, 
which may bo purified by solution in water, fractional 
precipitation with Na 2 C0 3 and repetition of the ether 
process, and finally, by re-crystallization of the result¬ 
ing hydrochlorate. 
{fPo he continued.) 
Ann. d. Cbem. u. Pharm., vol. clix. p. 518. 
MEETING AT HULL. 
A meeting of the members of the Pharmaceutical 
Society of Hull was held at their room on Tuesday, 
April 30th.; Mr. A. Pickering, President of the Hull 
Chemists’ Association in the chair. 
It was unanimously resolved to support the list of 
fourteen names proposed by the United Defence Associa¬ 
tion. 
