306 
Contributions  to  Pharmacy. 
Am.  Jour.  Pharni. 
June,  1894. 
combustion  gave  results  quite  different  from  those  obtained  by  Deich- 
mann,  so  that  the  presence  of  another  alkaloid  (containing  less  car- 
bon) in  the  material  suggested  itself.  By  forming  the  sulphate,  re- 
crystallizing  this,  then  liberating  the  base  and  crystallizing  from  al- 
cohol, the  alkaloid  was  purified  so  that  it  now  formed  white,  lustrous 
needles,  melting  at  132-5°  C,  insoluble  in  water,  soluble  in  alcohol, 
ether,  chloroform,  benzol  and  hot  petroleum-ether ;  exposed  to  light, 
it  slowly  becomes  yellow ;  the  alcoholic  solution  is  neutral  to  litmus 
and  phenolphtalein  ;  this  solution,  also  the  solutions  of  the  salts,  are 
laevogyre ;  the  nitrate,  hydrochlorate  and  hydrobromate,  especially 
in  presence  of  an  excess  of  the  acids,  are  difficultly  soluble ;  the  sul- 
phate, in  being  quite  soluble,  forms  an  exception  to  this  behavior. 
The  average  of  a  number  of  combustions  of  the  alkaloid,  C  70  60, 
H  6  31  and  N  4-13,  and  the  analysis  of  its  salts,  indicate  the  formula 
C20H21NO4,  isomeric  with  that  of  hydroberberine.  The  tests  for 
canadine  are  as  follows :  H2S04  dissolves  it  with  a  yellowish  color, 
slowly  taking  a  reddish  tinge,  and  after  long  exposure  to  air  the 
solution  becomes  milky-turbid ;  HNOs  dissolves  it  with  a  yellow 
color ;  Erdmann's  and  Froehde's  reagents  produce  a  transient,  olive- 
green  coloration,  changing  to  brownish -red  ;  vanadin-sulphuric  acid 
dissolves  it,  forming  an  olive-green  solution,  changing  to  a  black- 
brown.  Canadine  salts  are  not  changed  by  ferric  chloride  nor  by 
potassium  ferrocyanide  as  stated  by  Prescott ;  in  some  respects  the 
reactions  of  canadine  resemble  those  of  morphine,  hydrastine,  oxy- 
acanthine  and  berbamine :  Ferric  chloride  and  potassium  ferricy- 
anide  produce  a  blue-green  coloration  due  to  the  formation  of  Prus- 
sian blue ;  iodic  acid  is  reduced,  liberating  iodine  ;  if  a  little  bismuth 
sub-nitrate  be  sprinkled  on  a  solution  of  canadine  in  strong  sulphuric 
acid,  a  brown-black  color  is  developed. 
Of  the  salts  of  canadine  the  sulphate,  C20H21NO4H2SO4,  may 
be  obtained  anhydrous  in  large,  colorless,  tabular  crystals  or 
hydrated  with  one  molecule  water  in  the  form  of  groups  of  yellow- 
ish needles;  it  was  thought  at  first  that  there  were  here  the  sul- 
phates of  two  alkaloids,  but  as  in  the  recrystallization  it  was  possible 
to  get  from  both  salts  either  hydrated  or  anhydrous  crystals,  and  as 
the  base  separated  from  both  were  identical,  this  idea  had  to  be 
given  up.  The  hydrochlorate,  C20H21NO4HCl,  is  obtained  by  adding 
HC1  to  the  solution  of  the  sulphate,  when  it  may  separate  as  a  white 
crystalline  precipitate,  a  translucent  gelatinous  mass,  or  more  slowly 
