Two polymorphs of safinamide, a selective and reversible inhibitor of monoamine oxidase B.
Two polymorphs of safinamide {systematic name: (2S)-2-[4-(3-fluorobenzyloxy)benzylamino]propionamide}, C(17)H(19)FN(2)O(2), a potent selective and reversible monoamine oxidase B (MAO-B) inhibitor, are described. Both forms are orthorhombic and regarded as conformational polymorphs due to the differences in the orientation of the 3-fluorobenzyloxy and propanamide groups. Both structures pack with layers in the ac plane. In polymorph (I), the layers have discrete wide and narrow regions which are complementary when located next to adjacent layers. In polymorph (II), the layer has long flanges protruding from each side, which interdigitate when packed with the adjacent layers. N-H...O hydrogen bonds are present in both structures, whereas N-H...F hydrogen bonding is seen in polymorph (I), while N-H...N hydrogen bonding is seen in polymorph (II).
Laboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 607, India. sshiya@yahoo.com
Krishnan
K
Ravikumar
Balasubramanian
B
Sridhar
D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D001596:Benzylamines / Q000737:chemistry*; D003460:Crystallization; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008996:Monoamine Oxidase Inhibitors / Q000737:chemistry* / Q000494:pharmacology*
D001596:Benzylamines; D008996:Monoamine Oxidase Inhibitors; C092797:safinamide; D000409:Alanine