510 
Berberine  and  Derivatives. 
Am.  Jour.  Pharm. 
Oct.,  1884. 
ride,  ammonium  iodide,  potassium  chloride,  magnesium  chloride  and 
ammonia. 
Musculus  recommended  "  capillarimetry  "  more  particularly  for  the 
detection  of  alcohol,  acetic  acid,  etc.,  in  aqueous  liquids  ("  Jahresb.  d. 
Chem./'  1864,  p.  5),  and  similar  recommendations  were  previously  made 
by  Yalson  ("Jahresb.  Physik,"  1857,  p.  2). 
Experiments  on  the  coefficients  of  capillarity  of  numerous  sub- 
stances were  made  by  Wilhelmy  ("  Pogg.  Ann./5  cxix,  p.  177; 
"Jahresb.  d.  Chem./'  1864,  p.  6).  Chevreul  ("  Comp.  rend./'  lxiii, 
p.  399;  "Jahresb.  d.  Chem./'  1866,  p.  8)  called  "capillary  elective 
affinity"  the  property  of  linseed  oil  of  displacing  water  from  white 
lead,  and  of  water  displacing  oil  from  a  mixture  with  kaolin  or  with 
gray  clay. 
BERBERINE  AND  DERIVATIVES. 
The  formula  of  this  body,  according  to  Fleitmann,  is  C42H36N2G9,  ac- 
cording to  Kemp,  C42H34N207,  according  to  Stas,  C44TT38N2O10,  accord- 
ing to  Henry,  C42H38N2O10,  and  according  to  Serrius  and  Hlasivvetz, 
C20H17NO4,4jH2O.  From  numerous  analyses  of  the  free  base,  the 
hydrochloride,  nitrate,  and  sulphate,  E.  Schmidt  (Berichte  16,  2589), 
assigns  to  it  the  formula  C20H17NO44H2O.  Analyses  of  Hlasiwetz 
and  Gilm's  hydroberberine  (Annalen,  Suppl.,  2, 191),  its  hydrochloride 
and  nitrate  confirm  their  formula,  C20H21NO4.  From  its  behavior 
with  ethyl  iodide,  hydroberberine  must  be  a  tertiary  base.  Berberine 
is  converted  into  berberine  hydriodide  by  treatment  with  ethyl  iodide. 
The  hydroxide  obtained  from  hydroberberine  ethiodide  forms  color- 
less needles  melting  at  165°  ;  it  yields  crystalline  salts  with  hydro- 
chloric, nitric,  and  sulphuric  acids,  and  with  platinic  chloride.  On 
oxidizing  berberine  with  alkaline  permanganate,  a  bibasic  acid, 
C10H10O6  +  2H2O,  melting  at  165°,  is  obtained  apparently  identical 
with  hemipinic  acid. 
Derivatives.- — When  berberine  is  heated  in  a  retort  with  five  times  its 
weight  of  potassium  hydroxide,  it  blackens,  intumesces,  and  gives  off 
ammonia,  together  with  a  small  quantity  of  an  oily  liquid  which,  on 
examination,  was  found  to  be  quinoline.  From  the  residue  in  the 
retort,  two  acids  were  isolated,  which  were  found  to  have  all  the  pro- 
perties ascribed  to  them  by  Hlasiwetz  and  Gil  in  ;  O.  Bernheimer 
