^ptemberrSS"}    American  Pharmaceutical  Association.  517 
Prescott  and  Lloyd  were  chosen  for  the  two-year  term,  and  Profs.  Coblentz  and 
Kremers  for  one  year.    A  paper  on 
THE  CAFFEINE  COMPOUND  IN  KOLA. 
By  James  W.  T.  Knox  and  Albert  B.  Prescott. 
The  history  and  literature  of  kola  were  first  elaborated,  then  the  results  of 
an  investigation  of  the  fresh  seed  were  given  in  detail.  When  a  fresh  kola 
seed  is  cut  or  bruised,  a  chemical  change  immediately  takes  place,  as  shown  by 
the  rapid  change  of  color  of  the  cut  surface  from  pink  or  cream  color  to  red- 
brown.  On  this  account  the  authors  sought  a  method  of  exhausting  the  seed 
without  this  change  taking  place.  They  found  by  dropping  the  slices  of 
freshly  cut  kola  into  boiling  water,  or  water  at  a  temperature  above  650,  that 
this  result  could  be  effected,  but  that  alcohol  at  a  temperature  of  450  or  higher 
wasjbetter. 
For  pharmaceutical  purposes  they  found  the  best  solvent  for  extracting  kola 
to  be  alcohol  of  not  less  than  50  per  cent,  strength. 
The  authors  next  exhaustively  considered  the  subject  of  kola  assaying,  and 
offered  a  process  which  they  had  found  to  yield  uniform  results. 
In  regard  to  the  so-called  glucoside  of  kola,  or  kolanin,  they  found  the  dilute 
acids  to  be  unsuited  to  the  purpose  of  recovering  completely  the  alkaloids  from 
their  natural  combination,  so  that  lead  hydroxide  was  tried,  and  a  simple  and 
effective  process  of  liberating  the  caffeine  devised.  This  reaction  of  kolanin 
with  lead  hydroxide,  they  considered,  .indicated  a  tannin-like  character  for  the 
body.  "  There  is  reason  to  think  that  the  glucose  obtained  by  decomposing 
this  so-called  glucoside  with  mineral  acids  exists  primarily  in  combination  with 
the  tannin-like  body,  for,  after  chloroform  had  removed  all  the  caffeine  from 
the  mixture  of  alkaloids,  treatment  with  water  removed  nothing  further.  The 
liberation  of  glucose,  therefore,  is  not  necessarily  simultaneous  with  that  of 
caffeine,  nor  in  consequence  of  it.  This  was  further  shown  by  decomposing 
the  lead  salt  formed  by  the  red  coloring  matter,  through  treatment  with 
hydrogen  sulphide,  and  thereby  recovering  the  colored  body  previously  com- 
bined with  the  caffeine.  This  body  so  obtained  gave  all  tannin  reactions 
towards  iron  salts,  alkaloids,  gelatin,  etc.,  and  had  a  pronounced  astringent 
taste,  on  treating  it  with  dilute  mineral  acid,  in  the  manner  directed  by  text- 
books ;  very  positive  evidence  of  glucose  was  given,  not  only  by  its  behavior 
with  Fehling's  solution,  but  with  phenyl  hydrazine  as  well.  The  foregoing 
facts  would  seem  to  indicate  that  the  so-called  glucoside  is  a  combination  of 
caffeine  (and  theobromine)  with  a  glucoside  tannin." 
An  "artificial  kola-tannate  of  caffeine"  was  prepared  by  the  following 
process : 
An  aqueous  infusion  of  kola  was  poured  into  a  10  per  cent,  solution  of  caffeine 
acidulated  with  hydrochloric  acid.  The  presence  of  acid  was  necessary  to 
obtain  an  aqueous  caffeine  solution  of  sufficient  concentration,  and  especially  to 
avoid  the  re-solution  of  the  tannate  of  caffeine  which  takes  place  in  the  neutral 
solutions  in  the  presence  of  an  excess  of  either  tannin  or  caffeine.  The  precipi- 
tate, abundantly  formed,  was  rapidly  filtered  at  the  pump,  washed  with  cold 
water,  and  well  drained.  It  was  then  dissolved  in  alcohol,  and  filtered  to 
remove  insoluble  extraneous  matter  carried  down  in  precipitation.  The  alcohol 
was  then  distilled  off  under  reduced  pressure  until  the  solution  had  reached  a 
