Am.  Jour.  Pharm. 
Oct.,  1884. 
Berberine  and  Derivatives. 
511 
(Gazzetta,  13,  342-347),  is  at  present  engaged  in  studying  their  con- 
stitution. 
When  hydroberberine  is  heated  with  methyl  iodide  at  100°  in  a 
closed  tube,  a  yellow  crystalline  mass  is  obtained,  which  may  be  puri- 
fied by  repeating  crystallization  from  boiling  methyl  alcohol.  Lb  crys- 
tallizes in  the  trimetric  system  :  a  :  b:  e=  1-10332:  1 :  1.78880.  Ob- 
served forms,  001,  111,  113;  combinations,  001,  111,  113;  cleavage 
perfect,  001.  The  hydroberberine  methiodide,  C20H2lNO4,MeI,  is  spar- 
ingly soluble  in  water  or  alcohol  in  the  cold,  but  readily  when  heated. 
When  the  iodide  suspended  in  water  is  treated  with  silver  oxide,  it 
yields  the  corresponding  hydroxide,  which  may  be  obtained  in  crys- 
talline crusts,  C20H21NO4,MeHO  -J-  H20,  on  evaporating  the  solution. 
It  is  strongly  basic,  and  liberates  ammonia  from  ammonium  chloride. 
It  dissolves  in  cold  alcohol,  but  is  insoluble  in  ether.  On  adding 
hydrochloric  acid  to  its  aqueous  solution,  the  chloride  is  precipitated 
as  a  crystalline  powder.  The  platinochloride  crystallizes  in  beautiful 
lustrous  plates,  soluble  in  boiling  alcohol.  When  heated  in  a  sealed 
tube  at  150°,  the  hydroxide  is  decomposed,  with  elimination  of  methyl 
alcohol.  From  these  results,  the  author  infers  that  hydroberberine, 
like  berberine  itself,  is  a  tertiary  base. 
When  berberine  is  heated  with  methyl  iodide  and  methyl  alcohol, 
it  yields  a  methiodide,  C20Hl7NO4,MeI,  in  stellate  groups  of  slender 
needles.  On  treating  this  with  silver  oxide,  the  corresponding 
hydroxide  is  obtained,  very  similar  in  its  properties  to  the  hydrober- 
berine compound.    The  platinochloride  is  a  yellow  powder. 
Fleitmann  (Annalen,  59,  176)  in  his  paper  on  berberine  mentions 
the  formation  of  the  hydrochloride  of  a  base  containing  sulphur.  The 
author,,  following  Fleitmann's  directions,  added  yellow  ammonium 
sulphide  to  a  solution  of  berberine  hydrochloride,  collected  the  red 
precipitate,  dissolved  it  in  warm  water,  and  added  hydrochloric  acid  ; 
hydrogen  sulphide  was  evolved,  and  on  examining  the  solution  it  was 
found  to  contain  berberine  hydrochloride,  but  no  trace  of  sulphuretted 
base.  The  red  precipitate  mentioned  above  is  probably  a  persulphide 
of  berberine. 
On  treating  hydroberberine  with  iodine,  both  in  chloroform  solution, 
a  brownish  precipitate  is  obtained  consisting  of  berberine  hydriodide, 
C20H17NO4, HI.  It  is  easily  purified  by  crystallization  from  dilute 
alcohol.— Jour.  Chem.  Soc,  March  1884,  p.  339,  340. 
