Am;J0U,n  Pharm-)  Photochemical  Research. 
March,  19 17     J  J 
103 
A  desire  to  ascertain  the  nature  of  the  toxic  constituent  of  the 
nutmeg  was  the  chief  incentive  to  its  complete  chemical  examina- 
tion, and  this  yielded  results  of  considerable  interest.8 
Although  the  nutmeg  contains  a  considerable  amount  of  a  fatty 
oil,  the  more  important  product  is  the  essential  oil,  which  has  been 
found  to  be  of  very  complex  composition.  This  essential  oil  con- 
tains, for  example,  pinene,  camphene,  and  dipentene,  eugenol  and 
uoeugenol,  linalool,  borneol,  terpineol  and  geraniol,  safrole  and 
myristicin,  CnH^Og.  It  also  contains  formic,  acetic,  butyric,  and 
octoic  acids,  and  an  acid  of  the  composition  C13H1803,  all  in  the  form 
of  esters,  together  with  myristic  acid  in  a  free  state,  and  some  minor 
constituents  not  here  enumerated.  The  so-called  "  myristicol "  of 
earlier  investigators  is  now  known  to  have  been  a  mixture  of 
alcohols,  which  probably  consisted  chiefly  of  terpineol. 
Physiological  experiments  have  shown  that  the  toxic  properties 
of  nutmeg  are  due  to  the  compound  known  as  myristicin,  C^II^Os, 
which  is  a  3-methoxy-4  :  5-methylenedioxy-i-allylbenzene  : 
ch2— ch=ch2 
c 
HC  CH 
il  I 
O — C  C.OCH3 
CHi— OC 
This  compound  is  a  liquid,  possessing  only  a  faintly  aromatic 
odor  and  a  high  boiling  point,  171-1730  at  40  mm.  By  treatment 
with  metallic  sodium  or  with  an  alcoholic  solution  of  potassium 
hydroxide  it  is  converted,  through  the  change  of  the  allyl  into  a 
propenyl  group,  into  the  handsomely  crystalline  womyristicin,  which 
melts  at  440. 
The  chemical  interest  pertaining  to  nutmeg  is  not  restricted  to 
the  characterization  of  its  constituents,  or  even  to  the  determination 
of  the  physiologically  active  component,  for  the  primary  investiga- 
tion, as  is  frequently  the  case,  suggested  another  line  of  research 
which  led  to  results  of  considerable  importance.  It  was  conceived, 
for  example,  by  my  associate  in  these  investigations9  that  myristicin, 
8  Power  and  Salway,  Jour.  Chem.  Soc,  1907,  gi,  pp.  2037-2058,  and  1908, 
93,  PP-  1653-1659.    Also  Amer.  Jour.  Pharm.,  1908,  80,  pp.  563-580. 
9  Salway,  Jour.  Chem.  Soc,  1910,  gy,  pp.  1208-1219. 
