December 30,1871.] THE PHARMACEUTICAL JOURNAL AND TRANSACTIONS. 
525 
same way, an analogous reaction seems to ensue; the 
precipitate is very sparingly soluble in ether, and on 
treatment with hydriodic acid furnished a hydriodate of 
which 0-233 grm. dried at 100° gave 0-142 Agl; hence 
1 = 29-94 per cent.; the compound C 68 H 83 N 2 O 10 ,4HI 
requires 31-13 per cent., whilst the original substance 
requires 40-53 per cent. 
4. Action of Hydriodic Acid on some of the foregoing 
substances. 
As the action of water on the three compounds first 
described is to remove the elements of HI associated 
with the carbon radicals of the bases, it was thought pro¬ 
bable that by treating the products of the action of water 
on these compounds with strong boiling hydriodic acid, 
the HI thus lost might be again added on. A reaction 
of this nature does indeed take place, but does not always 
stop at the reproduction of the original bodies, another 
equivalent of HI being also added on; moreover, in 
some instances a number of molecules of H, O are like¬ 
wise taken up, and are not separated from the compounds 
ultimately formed even by some days’ exposure to a tem¬ 
perature of 100 °. 
On treating the compound C 68 H 80 N 4 O l 0 ,4HI with 
about ten parts of 55 per cent, of hydriodic acid (a little 
piece of phosphorus being also added to prevent separa¬ 
tion of iodine from the III by the heat) and heating to 
boiling, a syrupy liquid is obtained, from which water 
precipitates (after filtration of phosphorus) a tar resem¬ 
bling in all its physical characters the compound 
C 63 H sg I 2 N 4 0 12 ,4 HI; it contains, however, the elements 
of Hi-f 10HoO more than this substance. The same 
substance apparently is generated by treating the inter¬ 
mediate compound 
Ces H 81 1N 4 0 12 ,4III 
with hydriodic acid in the same manner. 
(A.) From the compound CggHgo^O^, 41; dried at 
100 ° till constant:— 
0 3565 grm. gave 0-483 C0 2 and 0-158 H 2 0. 
0-3835 grm. gave 0-278 Agl. 
(B.) (A) dried twelve hours more at 100°, had turned 
a much darker colour, probably indicating absorption of 
oxygen 
0'329 grm. gave 0-434 C0 2 and 0-155 H 2 0. 
0-561 grm. gave 0 - 419 Agl. 
(C.) From the compound C 63 II sl IN 4 O l0 ,4 HI:— 
0 377 grm. gave 0*485 C0 2 and 0-175 H 2 0. 
0-387 grm. gave 0-2855 Agl. 
Calculated. 
^68 • 
... 816 
36-69 
Hju 
... Ill 
4-98 
I r . 
... 889 
39-98 
n 4 . 
... 56 
2-52 
0 22 . 
'. . . 352 
15-83 
Found. 
A. 
B. 
~\ 
0. 
Mean. 
36*95 
35*98 
35-09 
36*01 
4-93 
5*24 
5*16 
5-11 
39-16 
40*35 
39*87 
39-79 
2224 100-00 
^68-^107^3-^4 022)^111. 
Hence this body is formed by the equations— 
Oc8 Hsol'U O 10 ,4 HI+3III -f-12 H 2 O — 
= ^68 Hjo- 1 3 N 4 6)22 ,4 HI. 
C 63 H 81 IN 4 O 10 ,4HI+2HI+12H 2 O = 
= O C sH 107 I 3 N 4 O 225 4 HI. 
On treating the compound C 63 H 8 S I 3 N 4 O ] 0 ,4HI in the 
same way, a product is obtained only differing from the 
original substance by one equivalent of HI; dried at 
100 °:— 
0-3995 grm. gave 0-6800 C0 2 and 0-197 H 2 0. 
0-3215 grm. gave 0-2200 Agl. 
Calculated. 
Found. 
CfiS. 
816 
46-36 
46*41 
h 93 . 
93 
528 
5-48 
I 5 . 
635 
36-09 
36-97 
N 4 . 
56 
3-18 
O 10 . 
160 
9-09 
CesHggIN.OjoAHI 
1760 
100-00 
Hence this body appears to have been formed by the 
reaction C 68 H gs N 4 O 10 , 4HI-j-HI=C 68 H 89 IN 4 O 10 ,4HI, 
no water having been taken up ; whilst in the case of the 
other non-iodized base, 3 molecules of HI and 12 of H 2 Q 
are assimilated. 
In order to see if the combined action of phosphorus 
and hydriodic acid would transform the compound 
C 68 H 86 I 2 N 4 0 12 ,4III 
into the body C 68 H 82 I 2 N 4 0 6 ,4HI, the former compound 
was dissolved in about 10 parts of 55 per cent, hydriodic 
acid, and boiled until most of the acid had volatilized; a 
considerable quantity of phosphoric acid was formed 
during the reaction, and on precipitating the compound 
produced with water, and drying at 100 °, the following 
numbers were obtained:— 
0-2795 grm. gave 0-3900 C0 2 and 0-136 H 2 0. 
0-4195 grm. gave 0-327 Agl. 
0-4225 grm. gave 0-333 Agl. 
Calculated. 
Found. 
n 
' I 
63 
11107 
1 7 . 
n 4 . 
Ole 
816 
38-42 
38-06 
107 
5-04 
5-41 
889 
41*85 
42U2 42-59 
56 
2-64 
256 
12*05 
C 63 H 103 T 3 N 4 O 16 ,4Hl 2124 100 00 
From these numbers it appears that the substance 
produced may be considered as formed by the reactions, 
C 6S H 86 I 2 N 4 0 12 , 4HI + 8HI = 
= I 8 + 61-LO + C 68 H 82 I 2 N 4 0 6 , 4II I. 
C 68 H 82 I 2 N 4 0 6 , 4 HI + HI + 10H 2 O = 
— L 63 ^ 10343 ^ 4 ^ 16 ) 4 HL 
It is not easy to explain why the reaction should stop 
■short at the end of the first stage, when codeia is treated 
with hydriodic acid and boiled up to 130°; possibly the 
presence of a much larger quantity of phosphorus acids 
in this case may tend to present the second reaction 
ensuing. 
5. Discussion of the Foregoing Results. 
From the complex constitution of the substances de¬ 
scribed above, it is at present thought unadvisable to 
attempt to give names to them. All the bodies previously 
mentioned may be regarded as being derived from one 
or other of the two bases C 17 H 21 N0 3 , andC^-H^NCR 
by multiplication of the molecule, and addition or sub¬ 
traction of the elements of water and of hydriodic acid. 
These two (hypothetical) bases contain H 2 more than 
morphia and deoxymorphia respectively; denoting the 
first by the symbol X, and the second by Y, the follow¬ 
ing general formulae will indicate all the compounds 
previously described:— 
4 X -j - m III -f n H 2 O, 
4 Y -j- mill -j- «H 2 0. 
Thus the following table illustrates the mutual rela¬ 
tions of the compounds described:— 
>urco of Compound. 
l) Codeia, HI, aud 
P at 150° . . . 
5) Do. 110° to 115° 
J) (A) treated with 
water or Na 2 C0 3 
)) Free base of (C). 
(A) treated with 
Na a C0 3 .... 
Formulae. 
C G8 II 8o r a ^ T 1 0 12 ,4HI=iX + GHI. 
CcsHr/ 3 NJU 0 ,4HI=4H+6HI—2H s O. 
C ea H 81 IX t 0 10 ,4HI=4X+5HI-2H a O. 
C C8 II 81 IX 4 0 10 =4X + HI —2II a O. 
