28 
Theocin. 
Am.  Jour.  Pliarni. 
January,  1903. 
ful  diuretic  of  this  class  of  vegetable  alkaloids.  -  By  the  synthesis  of 
Fischer  somewhat  larger  quantities  could  be  prepared,  but  at  a 
tremendous  expense.  It  was  the  endeavor  of  chemists  interested 
in  this  branch  of  chemistry  to  find  a  way  of  preparing  this  valuable 
remedy  so  that  it  could  be  used  commercially. 
I  am  exceedingly  pleased  to  state  that  such  a  synthesis  was  at 
last  discovered  in  the  laboratories  of  the  Farbenfabriken  of  Elber- 
feld.  The  new  synthesis  is  based  upon  Wilhelm  Traube's  research, 
published  in  the  Berichte  der  Chemisch.  Gesellsch.y  Vol.  33,  p.  3053, 
1900.  The  modifications  of  this  process  enable  the  Farbenfabriken 
to  produce  in  about  twelve  reactions  the  alkaloid,  which  is  named 
by  them  theocin,  on  a  larger  scale,  and  at  a  price  which  makes  its 
introduction  into  medicine  feasible. 
Although  some  vegetable  bases  and  alkaloids  had  been  previ- 
ously produced — thus  Ladenburg  prepared  coniin,  Hantzsch  trigo- 
nelline and  Willstaetter  cocain — yet  a  complete  synthesis  like  that 
of  theocin  has  not  hitherto  been  accomplished  on  a  commercial 
scale. 
This  synthesis  must,  therefore,  be  considered  as  one  of  the  most 
remarkable  achievements  of  organic  chemistry,  both  from  the  tech- 
nical and  scientific  point  of  view,  and  can  justly  be  compared  with 
the  synthesis  of  indigo. 
There  were  several  reactions  known  which  led  to  the  formation  of 
indigo,  but  none  was  economical ;  it  was  the  Badische  Anilin  and 
Soda  Fabrik  which  first  discovered  a  process  for  the  manufacture  of 
this  vegetable  product  by  synthesis.  The  same  is  true  of  theocin: 
there  was  the  ''Fischer,"  the  "  Traube  "  reaction ;  there  wras  the 
"Fischer  and  Ach"  modification  of  the  "Fischer"  synthesis,  yet 
none  of  these  reactions  could  be  carried  out  on  a  commercial  basis. 
The  Farbenfabriken  process  is  the  first  one  by  which  this  vegetable 
alkaloid  can  be  manufactured  on  a  large  scale. 
The  value  of  the  synthesis  of  theocin  will  be  seen  from  the  fact 
that  while  the  natural  product  cost  #93  an  ounce,  the  price  of  the 
synthetic  preparation  is  S2.30. 
In  regard  to  its  physical  and  chemical  characters  the  following 
may  be  said :  Theocin  appears  in  the  form  of  beautiful  colorless 
needles,  having  a  melting  point  of  2680  C.  It  is  difficultly  soluble 
in  cold  water  and  alcohol,  but  more  readily  in  warm  water ;  insol- 
uble in  ether.    It  is,  however,  much  more  soluble  in  cold  water  than 
