.Am  Jour.  Pharm. 
Nov.,  1891. 
Oil  of  Polei. 
551 
freely  in  hydrochloric  acid,  yielding  a  solution  which  gradually 
turns  brown,  but  it  is  only  very  sparingly  soluble  in  alkalis.  It 
reduces  ammoniacal  solutions  of  silver  and  copper  on  warming. 
The  hydrochloride,  C10H19NO2HCl,  separates  from  alcoholic  ether  in 
well-defined  rhombic  crystals,  a\b\c  —  0-6048  :  1  :  1-0477,  melts 
at  Ii7-n8°with  decomposition,  and  is  readily  soluble  in  water; 
its  specific  rotatory  power  is  [«]D  ==  — 32-43°.  The  benzoyl  deriva- 
tive, C10H18O:N-OBz,  prepared  by  treating  the  oxime  with  benzoic 
chloride  in  ethereal  solution,  crystallizes  from  dilute  alcohol  in 
colorless  needles  melting  at  137-138°  with  decomposition.  The 
acetyl  derivative,  C10H18O:N-OAc,  is  formed  when  the  oxime  is 
warmed  with  acetic  chloride  ;  it  crystallizes  in  long  needles,  and 
melts  at  1490. 
Pule 'gone 'amine,  C10H19ON,  is  obtained  when  the  oxime  is  treated 
with  hydriodic  acid,  and  the  crystalline  hydriodide  obtained  in  this 
way  warmed  with  excess  of  the  concentrated  acid ;  it  is  a  yellowish 
oil  having  a  bitter  taste  and  an  amine-like  odor,  and  it  decomposes 
when  heated  ;  it  is  only  sparingly  soluble  in  water,  but  readily  in 
ether  and  alcohol.  The  hydrochloride,  C10Hl9NO,HCl,  was  prepared, 
but  only  in  an  impure  condition,  by  treating  the  base  with  hydro- 
gen chloride  in  ethereal  solution ;  it  crystallizes  from  alcohol  in 
long  needles,  melts  at  117°,  and  is  readily  soluble  in  water,  alcohol, 
benzene,  and  glacial  acetic  acid,  but  only  moderately  easily  in  light 
petroleum,  and  sparingly  in  ether.  Pulegoneamine  phenylthiocarbi- 
mide,  C10H18O:N-CS-NHPh,-  is  precipitated  in  colorless  plates  on 
warming  a  benzene  solution  of  pulegoneamine  with  phenylthio- 
carbimide  ;  it  melts  at  I  p8°.  The  benzoyl  derivative,  CJ0H18O:NBz, 
separates  from  warm,  dilute  alcohol  in  colorless,  feathery  crystals, 
melts  at  100-5-101°,  and  is  sparingly  soluble  in  water,  ether  and 
benzene,  but  readily  in  alcohol.  The  methyl  derivative,  C10H18 
OiNMe,  prepared  by  boiling  the  amine  with  methyl  iodide,  and 
decomposing  the  product  with  potash,  is  a  light-yellow  oil ;  its 
platinochloride ,  (CuH21NO)2,H2PtCl6,  crystallizes  .in  well-defined  yel- 
low needles,  and  is  sparingly  soluble  in  alcohol  and  ether.  When 
pulegoneamine  is  boiled  with  concentrated  potash,  it  is  decomposed 
into  pulegone  and  ammonia;  methylpulegoneamine,  under  the 
same  conditions,  yields  pulegone  and  methylamine. 
An  additive  compound  of  the  composition  C]0H17BrO  is  deposited 
in  colorless  crystals  when  hydrogen  bromide  is  passed  into  a  well- 
