ADnN0°v.i;-if8h9arm-}  The  Synthesis  of  Alkaloids.  549 
loid  of  coca  leaves,  is  the  most  important,  from  a  physiological  point 
of  view. 
Ecgonine,  which,  as  is  well  known,  results,  along  with  benzoic  acid 
and  methyl  alcohol,  when  cocaine  is  heated  with  hydrochloric  acid, 
has  been  found  to  be  methyltetrahydropyridyl-oxy propionic  acid. 
Cocaine  can  be  made  synthetically  by  heating  this  ecgonine  with 
benzoic  anhydride  and  methyl  iodide,  and  a  series  of  analogous  artifi- 
cial alkaloids  have  been  made  with  phthalic,  cinnamic,  phenylacetic 
and  isovalerianic  acids,  combined  with  the  ecgonine.  The  production 
of  both  phenanthren  and  pyridine,  when  morphine  is  distilled  over 
zinc  dust,  has  been  known  for  years,  and  was  mentioned  in  my  previ- 
ous lecture  on  the  subject. 
Narcotine,  it  will  be  remembered,  is  decomposed  under  the  influence 
of  water  into  meconine  C10H16O4,  and  cotarnine  C12H13N03.  This  lat- 
ter is  capable  of  yielding,  under  the  influence  of  bromine,  dibrompyri- 
dine. 
Quinine  is  is  now  considered  to  be  a  derivative  of  a  partially  hydro- 
genated  diquinoline  corresponding  to  the  formula  C9H6  (OCH3)N- 
C9Hu(OH)N.CH3. 
That  cinchonine,  fused  with  caustic  potash,  yields  quinoline,  and 
that  strychnine,  under  the  same  treatment,  yields  also  quinoline,  to- 
gether with  indol,  while  brucine  yields  homologues  of  pyridine,  was 
noted  in  my  previous  lecture,  in  1883. 
Perhaps  of  greater  present  interest  is  the  manufacture  in  the  last 
few  years  of  a  large  number  of  synthetic  organic  compounds  which, 
while  not  generally  basic  or  alkaloidal,  are  equally  active,  physiolog- 
ically, in  a  variety  of  ways.  We  have  had  considerable  additions 
made  to  our  list  of  hypnotics,  antiseptics,  autipyretics  and  analgesics. 
In  a  lecture  I  delivered  last  January  before  the  Franklin  Institute  of 
this  city  on  the  "Debt  of  Medical  and  Sanitary  Science  to  Synthetic 
Chemistry/'  I  attempted  to  classify  the  more  important  of  these  newer 
synthetic  remedies.  They  were  there  arranged  in  five  groups,  accord- 
ing to  their  chemical  relationship. 
The  first  group  was  made  to  comprise  the  derivatives  of  methane 
CH4,  and  was  found  to  include  almost,  if  not  all,  of  the  hypnotics  and 
anesthetics.    The  list  as  there  given  was  as  follows  : 
Methylene  dimethylic  ether  (methylal)  CH2(OCH3)2 
Ethylidene  diethylic  ether  (acetal)  CH3.CH.(Od2H5)2 
Tertiary  amyl  alcohol  (araylene  hydrate)  (CH3  )2.C.C2H5.OH 
Paraldehyde  (CH3.COH)3 
