Am.  Jour.  Pharm. 
June,  1886. 
Cocaine  Benzoate. 
311 
mixing  the  two  substances  in  suitable  proportions  with  only  a  drop  or 
two  of  water  they  readily  combined,  forming  a  thick  liquid  which 
dried  up  on  exposure  to  a  surface  of  oil  of  vitrol  to  a  gummy  mass, 
and  after  some  days'  exposure  in  a  cold  place  it  presented  a  crystal- 
line structure.  Several  products  which  Mr.  Martindale  had  sent  to 
me  had  the  same  characters,  and  on  redissolving  these  in  about  their 
own  weight  of  moderately  warm  water,  solutions  were  obtained  which 
gave  on  cooling  and  after  standing  some  time,  acicular  crystals  quite 
different,  however,  from  those  obtained  from  a  solution  of  the  "  co- 
caine benzoate "  procured  from  Paris.  A  solution  of  these  crystals 
gave  with  ammonia  and  hydrochloric  acid  the  precipitates  character- 
istic of  cocaine  and  benzoic  acid  salts,  in  both  respects,  therefore,  dif- 
fering from  the  French  article. 
It  was  clear  therefore  that  cocaine  benzoate  could  be  obtained  in  a 
definite  crystalline  condition,  though  a  very  soluble  salt,  and  it  was 
also  clear  that  the  article  obtained  from  Paris,  under  that  name,  was  of 
a  different  nature.  A  further  examination  of  this  latter  substance 
enabled  me  to  ascertain  that  it  was  in  reality  the  same  substance  that 
I  have  previously  described1  as  being  produced  by  the  action  of  water 
and  heat  upon  cocaine — benzoyl  ecgonine — and  it  became  a  question 
how  this  substance  could  have  been  taken  for  cocaine  benzoate.  In 
seeking  for  a  solution  of  this  problem  I  tried  the  effect  of  rapidly 
evaporating  an  aqueous  solution  of  cocaine  benzoate  thinking  that  the 
benzoic  acid  might  thus  be  driven  off  and  the  decomposition  of  the 
cocaine  by  heat  and  water  brought  about  at  the  same  time.  But  this 
was  not  the  case,  and  I  was  equally  unsuccessful  when  a  solution  of  co- 
caine benzoate  in  spirit  wTas  rapidly  evaporated.  In  both  cases  the 
residue  left  was  cocaine  benzoate,  which  after  some  time  showed  signs 
of  becoming  crystalline.  Considering  the  source  from  which  this 
article  had  been  obtained  there  seemed  to  be  every  reason  to  suppose 
that  it  had  been  produced  as  the  result  of  some  unobserved  alteration 
that  had  taken  p'ace  in  the  attempt  to  prepare  a  true  cocaine  benzoate, 
and  it  remains  to  be  determined  how  this  change  took  place.  For  this 
purpose  I  have  some  experiments  still  in  progress,  and  have  received 
some  information  bearing  on  the  point  from  the  manufacturer  of  the 
article  supplied  from  Paris. 
I  may  take  this  opportunity  of  supplementing  the  account  I  form- 
erly gave  of  the  benzoyl  ecgoniue  obtained  by  heating  cocaine  with 
1  Ibid.,  p.  325. 
