NOTE ON NARCOTINE AND PRODUCTS OF ITS DECOMPOSITION. 213 
C 10 H ]0 O 0 + H Cl = C 8 H s 0 4 + C H 3 Cl+C 0 2 . 
Hemipimc Acid. Methyl-hypogallic 
Acid. 
By the action of reagents on cotarnine, C 12 H 13 N0 3 , Matthiessen and Foster 
have obtained a new acid, cotarnic add, C n H 12 0 5 , and other products which 
have not yet been thoroughly studied. The results of their experiments 
prove that cotarnine is a monomethylized compound, and consequently point 
to a normal cotarnine, ^HjjNOg, which has not yet been isolated. 
The next step in this elaborate investigation was the examination of the 
decompositions of narcotine itself. When narcotine was heated for some 
time with hydrochloric acid in a flask under a layer of paraffin, a new base 
was obtained. This base was found to have the composition expressed by 
the formula C 20 H 19 N 0 7 , and was evidently formed from the narcotine by the 
substitution of two atoms of hydrogen for two atoms of methyl. It was 
named methyl-normal narcotine for reasons which will presently be obvious. 
On continuing the research alone Dr. Matthiessen observed that, when nar¬ 
cotine was heated with hydrochloric acid for a short time only, one atom, of 
methyl was displaced by hydrogen ; and, further, that when narcotine was 
heated with fuming hydriodic acid, three atoms of methyl were displaced by 
three atoms of hydrogen. The two new bases thus produced were named 
respectively dAmetliyl-normal narcotine and normal narcotine. We have 
therefore four narcotines constituting a homologous series, thus :— 
Trimethyl-normal narcotine . . . C 22 H 23 N0 7 
(Ordinary narcotine ) 
Dimethyl-normal narcotine . . . C 21 E 21 N0 7 
Methyl-normal narcotine .... C 20 H 19 NO 7 
Normal narcotine.C 19 H 17 N0 7 . 
The three new bases are amorphous, and do not form crystalline compounds. 
In working with them Dr. Matthiessen experienced no ill effects; and, by 
taking grain doses, he was led to conclude that they have no marked physio¬ 
logical action. 
A recent observation made by this chemist, in conjunction with Mr. Wright, 
is specially noteworthy, as it explains the origin of meconin in opium extracts. 
By the action of water on narcotine at an elevated temperature, the base 
splits up into meconin and cotarnine, thus :— 
^ 22 ^ 23 ^ O?— C 10 H 10 O 4 + C 12 II 13 N 0 3 . 
Narcotine. Meconin. Cotarnine. 
This interesting discovery confirms the probable supposition that some of 
the numerous bodies which are named in analyses of opium are not actual 
educts, but merely products of decomposition. 
The investigation which I have ventured to bring under your notice is 
not directly connected with pharmacy, but. as its results greatly extend our 
knowledge of the constitution of the earliest-known opium alkaloid, I trust 
that I have not occupied your time in vain. The fact that we are greatly in¬ 
debted to the Messrs. Macfarlane for this extension of our knowledge 
deserves to be recorded in the proceedings of the Conference. 
[This note is based upon two papers published in the ‘ Philosophical Trans¬ 
actions.’] 
Professor Attfield, commenting upon Mr. Brough’s description of Dr. Matthiessen’s 
observations, said that he regarded his statements as involving an important discovery. 
It ought to remind them that in their chemistry they were dealing with matter under 
one particular set of circumstances. For example, they worked upon crude substances 
by means of water, and they possibly got as a result only certain products of the action 
