Am.  Tour.  Pharm.  \ 
July,  1 918.  / 
Analogues  of  Atropine. 
527 
I  express  my  appreciation  to  Dr.  W.  A.  Puckner  for  his  kind 
interest. 
Chemical  Laboratory, 
American  Medical  Association, 
Chicago,  III. 
ANALOGUES  OF  ATROPINE  AND  HOMATROPINE. 
By  Louis  F.  Werner. 
The  alkamine  tropine,  one  of  the  hydrolysis  products  of  atro- 
pine, is  changed  upon  oxidation  to  the  ketone  tropinone.  This 
ketone  is  closely  related  to  another  ketone  known  as  pseudopelle- 
tierine,  which  occurs  naturally  in  the  bark  of  the  pomegranate  tree. 
The  relationship  between  the  two  is  shown  by  the  following  struc- 
tural formulas : 
CH2 
Tropinone 
Pseudopelletierine 
As  can  be  readily  seen,  pseudopelletierine  differs  from  tropinone  in 
that  it  has  one  carbon  atom  and  two  hydrogen  atoms  more  than 
tropinone. 
Tropinone  upon  reduction  is  converted  into  two  stereoisomeric 
alcohols.  Upon  being  reduced  electrolytically,  or  with  concentrated 
hydriodic  acid  and  zinc  dust,  it  is  reduced  to  tropine,  but  if  reduced 
with  sodium  and  alcohol  it  yields  pseudotropine,  a  stereoisomer  of 
tropine.  These  two  stereoisomers  have  different  physical  proper- 
ties, and  the  esters  of  these  alcohols  with  the  hydroxy  acids  have 
different  physiological  properties. 
.  Pseudopelletierine  upon  reduction  also  gives  two  stereoisomeric 
compounds.  Ciamician  and  Silber2  found  that  an  alkamine  was 
formed  upon  reducing  pseudopelletierine  with  alcohol  and  sodium, 
which  they  named  methylgranatoline.    The  author  found  that  a 
1  From  the  Journal  of  the  American  Chemical  Society,  April,  1918. 
2  Ber.,  26,  2740  (1893). 
