CHEMICAL CONSTITUTION OF NAECOTINE. 
671 
rise to the production of methyl-noropianic acid and cotarnine, not of opianic acid and 
cotarnimide. 
and not 
Dimethyl-nornareotine. Methyl-noropianic acid. Cotarnine. 
c i9 H 15 (CH 3 ) 2 NO; + O = C 8 H 5 (CH 3 ) 0 5 + c n H 10 (CH 3 ) N0 3 , 
Opianic acid. Cotarnimide. 
0^ H 15 (CH 3 ) 2 N0 7 + O = C 8 H 4 (CH 3 ) 2 0 5 + c n H n no 3 . 
The yield of methyl-noropianic acid by either process is much less than the theoretical 
amount, probably from a secondary decomposition ; it may be obtained from the iron or 
platinum liquors by simple extraction with ether and purification by recrystallization 
from water ; if undecomposed narcotine is present in the base, opianic acid is likewise 
produced, and the two may be separated by fractional crystallization, the latter being 
much less soluble in cold water than the methyl-noropianic acid. A portion thus 
purified presented the physical characters of methyl-noropianic acid obtained by the 
action of hydrochloric on opianic acid, and gave the same reactions with ferric solutions : 
it contained no water of crystallization, and after drying at 100°, yielded the following 
numbers on analysis : — 
I. was made with a specimen prepared by the action of ferric chloride ; II. and III. 
by platinic chloride. 
I. 02200 grm. gave 0-4440 carbonic acid and 0-0870 water. 
II. 0 3130 grm. gave 0-6330 carbonic acid and 0-1250 water. 
III. 0-3050 grm. gave 0-6180 carbonic acid and 0-1200 water. 
Calculated. 
Found. 
( 
r 
I. 
II. 
III. N 
c 9 . . . 
oo 
o 
r— 1 
55-10 
55-04 
55-14 
55-26 
H 8 . . . 
8 
4-08 
4-39 
4-43 
4-37 
o 5 . . . 
. 80 
40-82 
— 
— 
— 
^9 H 8 0 5 . 
. 196 
100-00 
All attempts to procure the cotarnine formed in sufficient quantity and purity for 
analysis were fruitless. 
No other means of oxidation or decomposition tried were successful; the above 
reactions, however, tend to show that dimethyl-nornareotine is derived from narco tine 
by the substitution of H for CH 3 in the meconin radical, and not in the cotarnine, its 
rational formula being as follows, that of narcotine being* 
Narco tine. 
ch 3 i n 
(CnH 9 o 2 r 
(C 8 H 4 0)f 
(CH 3 ) 2 H }0 3 
Dimethyl-nornareotine. 
ch 3 j N 
(CnH 9 0 2 ){ 
(C 8 H 4 0) u 
(CH 3 )H 2 }o 3 . 
* Journal of the Chemical Society. 
4 u 2 
