242 
Cocaine  and  Atropine. 
/Am.  Jour.  Pharm. 
\       May,  1886. 
tests  to  them.  One  of  the  samples  consisted  of  the  crude  alkaloid  made 
in  South  America,  which,  it  is  true,  contains  43  per  cent,  of  matter 
insoluble  in  ether.  This  impure  cocaine  immediately  developed  the 
red  coloration  on  moist  phenolphtalein  paper;  not  so  the  other  speci- 
men of  cocaine  carefully  prepared  in  Dr.  Squibb's  laboratory. 
Cocaine  is  not  very  stable;  it  is  a  well-known  fact  that  solutions  of 
that  alkaloid  or  of  its  salts  do  not  keep  for  a  long  time  without  decom- 
position. If  the  purest  cocaine  be  dissolved  in  water  and  evaporated, 
the  residue,  after  having  repeatedly  undergone  this  treatment,  will  no 
longer  display  an  alkaloid  reaction  on  litmus  paper,  but  it  then  slightly 
reddens  litmus.1  This  experiment  proves  that  cocaine  already  splits  up 
by  the  mere  influence  of  boiling  water.  I  demonstrated  this  much  more 
strikingly  by  enclosing  a  little  cocaine  with,  say,  about  five  times  its 
weight  of  water,  and  heating  it  for  a  week  in  a  closed  tube,  only  in  a 
temperature  of  scarcely  100°  (212°  F.).  When  the  tube  was  opened, 
the  liquid  showed  now  a  very  strongly  acid  reaction.  The  alkaloid 
must  have  been  decomposed,  in  all  probability  into  benzoic  acid  and 
ecgonine.  I  do  not  know  whether  the  latter,  in  the  free  state,  has  any 
action  on  litmus,  but  from  my  experiment  it  would  appear  very  prob- 
able that  it  has  not;  at  least,  the  acid  reaction  of  the  acid  (benzoic,  no 
doubt)  produced  under  the  above-mentioned  conditions  is  not  altered 
by  the  presence  of  the  other  product  of  decomposition — ecgonine 
probably. 
I  thought  it  worth  while  to  examine  atropine  in  the  same  way.  This 
alkaloid,  as  I  have  shown  in  my  paper  in  the  Pharmaceutical  Journal, 
January  16,  1886,  p.  602  (see  Am.  Jour,  Phar.,  1886,  p.  129),  dis- 
plays a  very  decided  alkaline  reaction,  both  with  regard  to  litmus  and 
phenolphtalein.  This  was  no  longer  the  case  when  I  heated  the  atropine 
in  a  closed  tube  with  water  for  a  week.  The  solution,  however,  did  not 
redden  litmus,  but,  on  the  other  hand,  it  no  longer  displayed  an  alka- 
line reaction,  neither  on  red  litmus  paper  nor  on  phenolphtalein.  The 
said  aqueous  solution  of  atropine,  moreover,  produced  no  precipitate 
at  all  in  the  solution  nf  mercuric  chloride  (see  my  paper  just  alluded  to). 
It  is  evident,  therefore,  that  atropine,  as  well  as  cocaine,  is  decomposed 
merely  by  the  prolonged  influence  of  water  at  a  temperature  of  nearly 
100°  C. 
The  reactions  which  I  mentioned  may  prove  very  interesting  theoret- 
1  See  Notes  on  Cocaine,  etc.,  by  Dr.  Paul,  Phar.  Jour.,  xvi.,  (Oct.  17, 1885),  p.  325. 
