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XXII I. Researches into the Chemical Constitution of Narcotine, and of its Products of 
Decomposition. — Part III. By Augustus Matthiessen, F.R.S., Lecturer on Che- 
mistry in St. Bartholomew' s Hospital. 
Received February 18, — Read March 18, 1869. 
In Part II. of this investigation, carried out in conjunction with Professor Foster, it 
was stated that when narcotine is heated for some time with strong hydrochloric acid a 
new base was formed, which we called methyl-normal-narco tine, or methyl-nornarcotine, 
being derived from narco tine by replacing two atoms of methyl by two of hydrogen. 
In continuing the research into this subject, it has been observed that when narcotine 
is heated with hydrochloric acid, for only a short time, one atom of methyl is replaced 
by hydrogen ; and further, that when narcotine is heated with fuming hydriodic acid, 
three atoms of methyl are replaced by three of hydrogen, thus forming two other bases, 
the description of the preparation and properties of which form the subject of this 
Memoir. 
1. On the Action of Hydriodic Acid on Narcotine. 
When narcotine is heated with fuming hydriodic acid, iodide of methyl is evolved, 
and on investigating the residue it was found to consist of the iodide of a new base. 
To prepare this the following method was emyloyed : fuming hydriodic acid (made by 
converting iodine into hydriodic acid by sulphuretted hydrogen, evaporating the solu- 
tion, and, when cold, saturating it with gaseous hydriodic acid) is made to act on nar- 
cotine in a retort at the boiling-point of the mixture, when iodide of methyl is immedi- 
ately given off and a tarry mass left in the retort, which is chiefly the iodide of the new 
base. 
In two experiments made with 50 gratis, of narcotine, 457 and 46-2 grms. of iodide 
of methyl, and in a third experiment with 100 grms. of narcotine, 91 8 grms. of iodide of 
methyl, were obtained, 5T5 grms. and 103T grms. being the theoretical quantities 
required for the following reaction : — 
C 22 H 23 X0 7 + 3HI = C 19 H 17 N0 7 + 3CH 3 1. 
If the reaction 
C 22 N0 7 + 2HI = C 20 H 19 N0 7 + 2CH 3 1 
took place, the theoretical quantity of iodide would only be 34-3 grms. and 68*7 respect- 
ively. 
All endeavours to obtain the base in a state fit for analysis have been fruitless, owing 
to its rapidly oxidizing when exposed to the air ; to establish its composition the follow- 
mdccclxix. 4 T 
