298 poisons : THEIR effects and detection. [§ 361 . 
converted into codeine by heating with methyl iodide and caustic 
potash when the phenol hydroxyl of the morphine is alkylated, 
C 17 H 17 NO(OH) 2 +CH 3 I+KOH -> C 17 H 17 N0(0H)(0CH 3 )+KI+H 2 0 
Morphine. Codeine. 
When codeine methyl hydroxide is distilled it yields methyl- 
morphimethine (0H)(CH 3 0)C 17 H 16 0 = N —CH 3 +H 2 0 ; this heated with 
OH x 
HC1 gives methyldioxyphenanthrene _^3C 14 H 8 and dimethyloxethyl- 
CH 3 0 
amine OH—C 2 H 4 —N(CH 3 ) 2 . The first of these has been shown to be 
the monomethyl ether of dioxyphenanthrene or methyl morphol ; the free 
base from this is known as morphol , and has been proved to be 3, 4-dioxy- 
phenanthrene, and methyl morphol is 3-methoxy-4-oxyphenanthrene, 
OH OH OH_OCH 3 
Morphol. Methyl morphol. 
The nitrogenous base formed on heating methylmorphimethine 
ch 2 oh 
with HC1 may be represented thus, | dimethyl ethyl 
CH 2 N(CH 3 ) 2 
oxethylamine, and from the formation of this compound morphine is 
considered to contain an oxazine ring of the form 
0 
H,C CH, 
H 2 C v ch 2 
NH 
this is called morpholine. 
Morphine and codeine thus appear to be ring systems containing the 
phenanthrene complex in connection with a morpholine ring, and the 
following formula has been proposed for morphine, 
CH 
HO-C CH 
CH 2 -0- 
C 
C\/\ 
c 
H 
CH, 
N 
CH, 
HO 
H 
C 
)>c \y 
CH 
CH 
C 
CH, 
CH, 
Morphine. 
