ATa?uaryfl900m-}  Constitution   of  the    Alkaloids .  2$ 
formula  of  Knorr  is  usually  accepted  as  very  near  the  truth,  and  as 
such  we  will  accept  it.  It  is  a  morpholine  derivative  of  the  hydro- 
carbon phenanthrene,  and  the  questions  remaining  open  are  at 
which  of  two  of  the  three  benzene  rings  of  phenanthrene  the 
morpholine  ring  is  attached,  and  (2)  exactly  where  the  two  hydroxyls 
are  located.  I  will  give  you  both,  and  you  can  have  your  choice : 
OH 
CH     CH  O 
CH  OH 
HC       C         CH  CH2 
III  I  OH.C  CH 
C       C         CH         CH2  I         I  I 
/\/     \/        X/  HC       C  CH 
OH.C        C      CH2        N.CH3  \/\  /\ 
I  !  C        C  CH 
HC        CH  I  I  I 
HC        C         CH  CH9 
C 
H  Morphine.  CH      CH2  N.CH3 
There  can  be  no  doubt  that  this  question  of  final  doubt  will  ere 
long  be  settled.  What  was  said  of  morphine  is  equally  true  of 
quinine,  for  one  investigator  of  the  constitution  of  this  alkaloid 
alone,  Konigs,  could  fill  a  good-sized  quarto  volume  with  his  own 
work.  The  question  is,  however,  further  removed  from  solution 
than  in  case  of  morphine,  for  in  case  of  quinine  there  is  an  entire 
group,  C10H15(OH)N,  that  is  more  or  less  a  mystery.  On  the  face 
of  it,  it  appears  like  a  quinoline  group,  but  it  has  been  settled  that 
it  is  not,  but  rather  a  pyridine  group,  and  tetra-hydrated  at  that, 
and  somewhat  similar  to  tropine  and  ecgonine.  The  fact  that  cin- 
choloiponic  acid,  an  oxidation  product  of  cinchonine,  is  both  iso- 
meric with  tropic  acid  and  of  very  similar  constitution,  indicates 
this  very  strongly.  At  any  rate,  we  know  that  quinine,  quinidine 
and  quinicine  are  identical  constitutionally,  but  are  stereochemic 
isomers,  and  the  same  is  true  of  cinchonine,  cinchonidine  and  cin- 
chonicine.  The  difference  between  the  two  groups  is  one  methoxyl 
group,  OCH3,  as  the  formulas  below  indicate: 
C10H]5(OH)N  C10H15(OH)N 
H         /  H  I 
c     c  c  c 
HC       C        CH  CH3OC       C  CH 
III  III' 
HC       C        CH  HC       C  CH 
C        N  C  N 
H  H 
Cinchonine,  etc.  Quinine,  etc. 
