CHEMICAL CONSTITUTION OF NAECOTINE. 
677 
and is capable of crystallizing with half a molecule, or with a whole molecule of water 
(Part I. p. 349, and Part IV. p. 673). 
6th. When cotarnine is heated with dilute nitric acid, under certain not clearly 
understood conditions, cotarnic acid is produced together with methylamine, 
C 12 H 13 NO s + 2H 2 O = C u H 12 0 5 + C 3 H 5 N ; 
with strong nitric acid, as stated by previous observers, apophyllic acid is produced ; 
other oxidizing agents give no definite results (Part I. p. 359, and Part IV. p. 673). 
7th. When cotarnine is heated with strong hydrochloric acid, chloride of methyl is 
formed and hydrochlorate of cotarnamic acid, 
C 12 H 13 N0 3 + H 2 O + 2H Cl = CH 3 Cl + C u H 13 N0 4 , H Cl. 
Hydriodic acid produces a similar reaction, only one equivalent of CH 3 being eliminated 
for one of cotarnine (Part I. p. 360). 
8th. Opianic acid treated with bichromate of potassium and dilute sulphuric acid 
becomes oxidized to hemipinic acid (Part IV. p. 673), 
Cio Hio O5 + O = C 10 H 10 0 6 . 
9th. Opianic acid under the influence of nascent hydrogen (as with sodium-amalgam 
or zinc and sulphuric acid) is reduced to meconin (Part I. p. 354). 
C 10 H 10 0 5 + H 2 = C 10 H 10 0 4 + H 2 O. 
10th. Opianic acid heated with caustic potash splits up into meconin and hemipinic 
acid (Part I. p. 352). 
2C 10 H 10 O 5 =C 10 H 10 O 4 + C 10 H 10 O 6 . 
11th. When opianic acid is heated with excess of hydrochloric acid, chloride of methyl 
is formed, and hydrogen substituted for methyl in the opianic acid : it appears probable 
that two distinct substances are thus produced, noropianic acid and methyl-noropianic 
acid — the former by substitution of H 2 for (CH 3 ) 2 , and the latter of H for CH 3 ; only 
the latter has been isolated in a pure state, the former decomposing spontaneously, 
C 10 H 10 0 5 + 2 HC1 = C 8 H 6 0 5 + 2CH 3 Cl, 
C 10 H 10 0 5 + HC1 = C 9 Hg 0 5 + CH 3 Cl. 
Hydriodic acid apparently produces similar decompositions ; like opianic acid, methyl- 
noropianic acid is monobasic (Part II. p. 657). 
12 th. All experiments to oxidize meconin to opianic or hemipinic acids or any other 
product have proved failures. 
13th. Meconin treated with excess of hydrochloric or hydriodic acid forms chloride or 
iodide of methyl, and a body derived from meconin by substitution of H for CH 3 (methyl- 
normeconin) : 
C10 H 10 0 4 + HC1 = C 9 Hg 0 4 + CH 3 Cl. 
Attempts to substitute H 2 for (CH 3 ) 2 did not yield anything capable of isolation in a 
pure state (Part II. p. 660). 
MDCCCLXIX. 4 X 
