Am.  Jour.  Pharm. 
June,  1894. 
Contributions  to  Pharmacy. 
307 
in  small  lustrous  scales ;  exposure  to  light  and  air  slowly  develop  a 
yellow  color.  The  nitrate  C20H21NO4HNO3  obtained  like  the  hydro- 
chlorate,  forms  small,  lustrous,  white  scales.  Canadine- platinic  chlo- 
ride (C20H21NO4HCl)2Ptcl4,  is  obtained  as  a  yellow  amorphous  pre- 
cipitate. Canadine-auric  chloride,  C20H21NO4HCl  +  AuCl3,  forms  a 
red-brown  flocculent  precipitate.  Methyl  iodide  at  ordinary  tem- 
perature unites  with  canadine,  forming  pale  yellow  crystals  C20H21 
N04CH3I,  which  melt  at  228-2320  C. 
The  behavior  of  canadine  towards  alkaloidal  reagents,  its  change 
of  color  when  exposed  to  light,  and  the  fact  that  the  mother- 
liquors  of  canadine  sulphate  exposed  to  light  and  air  contained 
berberine  sulphate,  indicated  the  close  relationship  of  these  two 
alkaloids ;  another  important  observation  in  this  connection  was 
that  iodine,  acting  upon  the  alcoholic  solution  of  canadine,  was 
decolorized,  producing  an  intensely  yellow-colored  solution,  from 
which  an  abundant  separation  of  small  yellow  crystalline  needles 
was  noted  after  a  short  time.  This  deposit  of  crystals  was 
found  to  consist  of  berberine  hydriodate  and  the  hydriodate  of 
another  base  resembling  canadine,  but  melting  at  1400  C.  instead 
of  132-5°  C.  These  reactions  indicate  that  canadine  C^H^NC^ 
is  Jetrahydroberberine  (berberine  C20H17NO4),  and  that  the  base 
just  mentioned  may  be  an  intermediate  product  between  canadine 
and  berberine.  From  the  action  of  iodine  upon  canadine  at 
iOO°  C.  were  isolated  golden-yellow,  lustrous  needles,  agreeing  in 
all  respects  with  berberine  hydriodate,  C20H17NO4HI ;  from  them 
derivatives  were  prepared,  agreeing  in  all  respects  with  berberine 
hydrochlorate  and  berberine  aurichloride.  By  the  action  of  zinc 
and  sulphuric  acid  the  yellow  solutions  of  the  hydrochlorate  and  hy. 
driodate  were  nearly  decolorized ;  ammonia  separated  from  these 
solutions  a  gray-white,  flocculent  precipitate,  which,  after  recrystal- 
lization  from  boiling  alcohol,  was  dissolved  in  chloroform  and  covered 
with  a  layer  of  alcohol ;  the  crystalline  needles  first  formed  were 
readily  transformed  into  the  octahedral  form  characteristic  of  hydro- 
berberine,  which  were  found  to  melt  at  1 66—  1 67  0  C,  thus  demon- 
strating that  canadine  could  be  changed  into  the  isomeric  hydro- 
berberine.  Frank  X.  Moerk. 
