300  Chemistry  of  the  Coca  bases.  {AmjESS"wSfrm' 
stance  did  not  give  off  methyl,  but  when  boiled  with  dilute  acid  it 
melted  to  a  yellowish  oil,  and  after  some  long  time  was  completely 
decomposed,  yielding  ecgonine  and  an  acid  that  was  not  more  closely 
examined.  The  composition  of  this  substance  is  represented  by  the 
formula  C18H19N04. 
It  is  probable,  therefore,  that  the  acid  product  contained  two  atoms 
less  hydrogen  than  cocaic  acid,  and  that  its  relation  to  that  acid  is  the 
same  as  that  of  acrylic  acid  to  propionic  acid.  For  that  reason  I  give 
the  acid  the  name  of  cocrylic  acid,  the  substance  it  is  derived  from  that 
of  oocrylecgonine,  and  the  methylated  cocrylecgonine,  which  would 
correspond  with  cocamine,  that  of  cocryJarniDe.  The  brownish-yellow 
oil  observed  in  the  decomposition  of  the  so-called  isatropylcocaine  by 
hydrochloric  acid  may  be  for  the  most  part  only  cocrylecgonine,  and 
its  production  may  be  due  to  the  presence  of  some  cocrylamine  in  the 
isatropylcocaine.  That  moreover  is  probably  the  reason  that  the  pro- 
duct obtained  by  Liebermann  from  the  crude  bases  possessed  poison- 
ous characters. 
The  liquid  from  which  cocamine  had  been  separated  by  fractional 
precipitation  by  ammonia  still  contained  substances  that  could  be  ex- 
tracted by  petroleum  spirit  and  obtained  as  a  tolerably  liquid  oil  that 
was  readily  soluble  in  dilute  hydrochloric  acid.  Platinic  chloride 
added  to  the  solution  gave  a  pale  yellow  precipitate  which  contained 
19*44  per  cent,  platinum  after  drying  at  1 10°  C.  The  last  fraction  gave 
only  1  s '22  per  cent,  platinum,  and  therefore  the  substance  was  a  mixture. 
This  mixed  substance,  when  boiled  with  dilute  hydrochloric  acid, 
yielded  some  ecgonine  as  hydrochloride  and  an  oily  non- volatile  base, 
together  with  some  hygrine.  The  latter  was  separated  by  adding 
baryta  and  shaking  out  with  ether.  There  were  also  obtained  cocaic 
acid,  apparently  corresponding  in  quantity  to  the  ecgonine,  much  cin- 
namic  acid 1  and  some  benzoic  acid.  The  cinnamic  acid  was  sepa- 
rated in  the  form  of  a  lime  salt,  crystallizing  in  small  needles  very 
sparingly  soluble  in  cold  water  and  consisting  of  (C9H702)2Ca+3H20. 
The  melting  point  of  the  acid  was  131°  C,  or  rather  less  than  that 
observed  by  Kraut,  Liebermann  and  Frankfeld.  With  permanganate 
it  yielded  benzoic  aldehyd.  In  regard  to  the  acid  said  to  be  benzoic  it 
may  be  mentioned  that  its  melting  point  was  121°  C,  and  that  it  gave 
the  reactions  characteristic  of  benzoic  acid. 
1  The  occurrence  of  cinnamic  acid  among  the  products  of  decomposition  of 
coca  bases  was  known  to  me  long  before  the  publication  of  the  fact  by  Frankfeld. 
