Am>Ju°nUer;il9h9arm-}  Hydrastine  Hexiodide.  261 
is  easily  decomposed  by  boiling  with  mineral  acids,  with  the  libera- 
tion of  pure  berberine. 
hydrastine.  In  the  elaborate  research  which  has  established  the  existence  of 
canadine,  Prof.  B.  Schmidt  (1894  :  Arch.  d.  Pharm.,  232,  136)  prepared  it  from 
a  crude  hydrastine,  and  also  from  a  crude  canadine  hydrochloride  made  for  him 
by  B.  Merck,  of  Darmstadt.  In  the  purification  the  canadine  was  precipitated  as' 
a  salt  of  nitric  acid.  The  insolubility  of  its  salts  with  mineral  acids  would  be 
likely  to  carry  it  into  the  crude  salts  of  berberine,  when  these  are  precipitated 
for  the  removal  of  this  alkaloid.  Prof.  J.  U.  L4oyd  ("  Drugs  and  Medicines  of 
North  America,"  Cincinnati,  1885,  pp.  139-141,  127)  has  shown  that  strong 
acidulation  with  hydrochloric  acid  is  necessary  to  the  full  precipitation  of  the- 
berberine,  and  that  when  the  filtrate  is  precipitated  by  ammonia  at  the  neutral 
point  any  further  precipitation  caused  by  an  excess  of  the  ammonia  consists 
of  or  contains  berberine,  as  a  result  of  its  incomplete  removal  by  acid  pre- 
cipitation. Professor  L/loyd  was  evidently  right  in  his  conclusion  that  the 
method  of  Burt  (1875  :  Am.  J.  Pharm.,  /7,  481)  for  "a  third  alkaloid"  yields 
berberine  unless  this  have  been  more  closely  removed  by  the  strong  acidula- 
tion just  referred  to.  But  since  the  research  of  Schmidt  it  appears  likely  that 
canadine  would  be  precipitated  with  the  berberine  by  strong  acidulation.  And 
the  discrepant  accounts  of  the  color  of  the  third  alkaloid  are  explained  by  the 
discovery  that,  though  it  is  colorless,  in  purity,  it  acquires  color  by  exposure 
to  light  and  air,  tetrahydroberberine  (C20H21NO4)  being  oxidized  into  berberine 
itself  (C20HnNO4)  (Schmidt,  Arch.  d.  Pharm.,  232,  148).  Howrever,  neither 
Hale  nor  Burt  worked  with  enough  of 'the  hydrastis  to  obtain  canadine  in  the 
purity  and  amount  required  for  any  satisfactory  description  or  conclusion. 
They  did  not  claim  to  individualize  or  name  the  alkaloid  ;  indeed,  the  note 
of  Hale  only  raised  the  question  of  its  existence.  Professor  Schmidt,  who  had, 
as  he  said,  worked  more  than  ten  years  with  hydrastis  alkaloids,  found  it  need- 
ful to  operate  upon  50  kilograms  of  the  drug,  and  availed  himself  of  a  crude 
product  accumulated  in  a  manufactory.  This  was  about  five  }*ears  after  that 
Wilhelm  had  made  a  report  from  the  laboratory  of  Professor  Schmidt  (1888  : 
Arch.  d.  Pharm. ,  226,  320)  upon  a  third  alkaloid  in  hydrastis.  In  this  report 
the  finding  of  this  alkaloid  was  ascribed  to  Hale  (1873:  Am.  J.  Pharm.,  45, 
247),  Burt  {toe.  tit.)  and  Lerchen  (1878:  Am.  J.  Pharm.,  jo,  470),  and  the 
reader  might  infer  that  the  name  canadine  had  been  proposed  by  Hale  and 
Burt.  Consequently,  in  the  second  edition  of  "  Beilstein  "  (III,  491)  "cana- 
dine" is  described  upon  no  other  authority  than  that  of  Hale  and  of  Burt.  In 
Beilstein's  third  edition,  with  fuller  description,  the  authority  of  B.  Schmidt, 
Privatmitth,  is  prefixed.  The  alkaloid  examined  by  Wilhelm  in  1888,  not 
analyzed  because  of  insufficient  quantity,  was  prepared  from  ammoniacal  solu- 
tion extracted  with  acetic  ether.  That  observed  by  Hale,  by  Burt  and  by 
Lerchen  was  obtained  by  precipitation  with  ammonia  in  some  excess.  The 
first  elementary  analysis  was  made  by  D.  Deichmann  (Inauguraldissert,  Ros- 
tock, 1892).  In  the  analysis  of  Schmidt  his  figures  differ  from  those  of  Deich- 
mann, due  to  greater  purity  of  preparation  (Arch.  d.  Pharm.,  232,  139). 
Deichmann  reported  a  cryoscopic  determination  of  the  molecular  weight. 
Zeisel  (Inauguraldissert,  Dorpat,  1892)  determined  the  methoxy  groups  in 
canadine. — A.  B.  Prkscott. 
