Molecular structures of two indole alkaloids, evodiamine and rutecarpine, from evodia fruit

Evodiamine,C 19 H 17 N 3 , is orthorhombic, P2 1 2 1 2, a=13.654(2) Å, b=20.727(1) Å, c=5.2370(3) Å, V=1482.1(2) Å 3 , Z=4. Rutecarpine, C 18 H 13 N 3 O, is monoclinic, P2 1 /a, a= 26.909(1) Å, b=7.398(1) Å, c=14.468(1) Å, ß=98.672(5)°, V=2847.3(4) Å 3 , Z=8. Although rutecarpine takes an essentially planar structure, evodiamine is folded in the middle of the molecule and the two halves are nearly perpendicular to each other. The marked differences of the three-dimensional structures is considered to be responsible for the significant difference of the body temperature retaining effects of these alkaloids.