236  Researches  on  Opium  Alkaloids.  {Am'£^iSarm- 
RESEARCHES  ON  OPIUM  ALKALOIDS.1 
By  T.  and  H.  Smith  and  Co. 
Xanthaline. — This  new  alkaloid  was  discovered  in  our  laboratory 
as  far  back  as  1 88 1 ,  but,  owing  to  various  reasons,  publication  has 
been  deferred  until  now.  It  occurs  in  the  acid  mother  liquids 
resulting  from  the  crude  hydrochlorates  of  morphine  and  codeine  in 
the  Robertson  Gregory  process,  and  is  precipitated  therefrom,  along 
with  narcotine,  papaverine,  and  many  impurities,  on  diluting  and 
carefully  neutralizing  those  liquids. 
That  precipitate  is  purified  by  washing  with  dilute  caustic  soda 
and  hot  water,  and  subsequent  treatment  with  weak  spirit.  The 
remaining  crystals  are  dissolved  in  boiling  water,  with  addition  of 
as  much  hydrochloric  acid  as  is  requisite  to  dissolve  three-fourths 
of  them,  the  remaining  fourth  being  then  added,  and  the  whole 
allowed  to  boil  for  some  time.  After  filtration,  the  insoluble  residue 
is  well  washed  with  hot  water  and  again  treated  with  boiling  spirit. 
A  considerable  portion  still  remains  undissolved,  and  this  is  now 
dissolved  in  dilute  hydrochloric  acid  and  filtered  hot.  If  the  liquid 
be  at  all  concentrated,  the  filtrate  will  solidify  into  a  spongy  mass 
of  crystals,  which,  after  being  freed  from  the  dark  liquor,  present  a 
similar  appearance  to  narceine,  but  of  bright  yellow  color.  Recrys- 
tallization  from  dilute  hydrochloric  acid  and  washing  with  strong 
spirit  renders  the  salt  of  the  new  alkaloid  pure. 
The  alkaloid  itself  is  readily  precipitated  from  the  hydrochlorate 
by  boiling  with  water,  and  is  left  behind  as  a  white  powder  on 
heating  the  hydrochlorate  above  ioo°  C.  for  several  hours.  From 
a  hot  alcoholic  solution  of  the  salt,  it  is  thrown  down  by  an  alkali 
'  as  a  white  crystalline  powder,  insoluble  in  water  and  in  alkalies, 
sparingly  soluble  in  boiling  spirit,  more  easily  in  benzene,  and  very 
easily  in  chloroform.  Its  melting  point  is  2060  C.  It  is  a  weak 
base,  but  forms  well-defined  salts  with  mineral  acids  if  these  are 
used  in  excess,  all  these  salts  possessing  a  more  or  less  intense 
yellow  color.  The  nitrate  is  of  a  bright  orange  color.  In  accord- 
ance with  this  very  characteristic  property  of  forming  yellow  salts 
the  name  xanthaline  (savdos  =  yellow  ;  tils  =  salt)  was  chosen  for 
this  new  alkaloid. 
1  From  papers  read  before  the  Pharmaceutical  Society  of  Great  Britain  at  the 
evening  meeting  in  Edinburgh,  March  15.  Phar.  Jour,  and  Trans.,  March  25, 
i893,  p.  793-795- 
