Am.  Jour.  Pharm.) 
Nov.,  1883.  J 
Constitution  of  the  Alkaloids. 
549 
hydrogen,  marsh  gas  and  ethylene.  Heated  with  bromine  water  to 
1 20 °C,  it  decomposes  into  bromoform,  carbon  dioxide,  nitrogen  and 
pyridine.  When  its  alcoholic  solution  is  treated  with  ferricyanide  of 
potassium  it  is  oxidized  to  dipyridine  CioHiyNg.  Potassium  perman- 
ganate, chromic  or  nitric  acid  oxidises  it  to  nicotinic  acid,  C6H5NO2, 
which  is  simply  pyridine-carboxylic  acid,  C5H4N  (COOH),  and  which, 
distilled  over  quick-lime,  yields  pyridine  C5H5N. 
Turning  now  to  the  non-volatile  and  oxygenized  bases,  we  take  up 
first  the  opium  alkaloids.  Morphine,  C^^H^gNO^,  is  a  tertiary  amine, 
and  appears  to  contain  a  hydroxyl  group  like  phenols,  to  which  class 
of  bodies  it  has  some  analogies,  as  is  shown  in  its  reaction  with  ferric 
chloride.  Its  methyl  ester,  which  can  be  formed  from  it,  is  Codeine, 
one  of  the  accompanying  alkaloids  of  opium.  Besides  the  methyl 
■derivative,  however,  others  are  possible,  and  several  have  been  recently 
prepared,  giving  rise  to  a  class  of  artificial  alkaloids  known  as  codeines. 
Morphine,  rapidly  distilled  over  zinc  dust,  yields  phenanthren,  tri- 
methyl- amine,  pyrrol,  pyridine,  quinoline,  and  other  bases.  The 
action  of  strong  hydrochloric  acid  upon  morphine  changes  it  into  apo- 
morphine  by  the  withdrawal  of  a  molecule  of  water. 
Ferricyanide  of  potassium  and  caustic  soda  solution  change  morphine 
into  oxydimorphine,  C34H3gN20g.  When  heated  with  strong  potassium 
hydrate,  it  yields  methylamine. 
Narcotine,  another  of  the  opium  alkaloids,  when  heated  with  man- 
ganese dioxide  and  sulphuric  acid,  is  oxidised  and  splits  apart  into  opi- 
anic  acid,  CjoHj^Os,  and  cotarnine,  Ci2Hj3N03.  This  latter,  by  careful 
oxidation,  yields  apophyllenic  acid,  CgH^NO^,  and  this,  on  heating 
^ith  hydrochloric  acid  to  240°  C,  yields  pyridine-dicarboxylic  acid, 
C5H3N  (COOH)2.  The  base  cotarnine  also  results  from  the  prolonged 
heating  of  narcotine  with  water  alone.  In  this  case,  instead  of  opianic 
acid,  its  reduction  product  meconine,  CioIIio04,  is  produced. 
Meconic  acid,  C7H4O7,  which  is  found  in  opium  in  combination  with 
the  different  bases,  has  also  been  investigated.  By  acting  upon  meconic 
acid  with  ammonia,  comenamic  acid  is  formed,  and  this  latter,  when 
heated  with  zinc  dust,  yields  pyridine. 
If  we  go  now  to  the  cinchona  alkaloids,  we  meet  with  exceedingly 
interesting  results.  Quinine,  C20H24N2O2,  when  carefully  oxidised 
with  chronic  acid  or  potassium  permanganate,  yields  a  series  of  pro- 
ducts. First  is  formed  quitenine,  C19H22N2O4,  a  weak  base,  then 
quininic  acid,  CnHgNOg,  then  the  so-called  oxycinchomeronic  acid. 
