Abstract

In the title compound, C26H28N5O2+·Cl-·CH3OH {systematic name: 4-(2-carbamoyl-1-benzo-furan-5-yl)-1-[4-(5-cyano-1H-indol-3-yl)but-yl]piperazin-1-ium chloride methanol monosolvate}, the protonated piperazine ring adopts a chair conformation. The indole ring plane is nearly perpendicular to the benzo-furan ring system, with a dihedral angle of 85.77 (2)°. In the crystal, the organic cations, Cl- anions and methanol solvent mol-ecules are linked by classical N-H⋯O and N-H⋯Cl hydrogen bonds, and weak C-H⋯O and C-H⋯π inter-actions into a three-dimensional supra-molecular architecture.

Highlights

  • In the title compound, C26H28N5O2+ClCH3OH {systematic name: 4-(2-carbamoyl-1-benzofuran-5-yl)-1-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-ium chloride methanol monosolvate}, the protonated piperazine ring adopts a chair conformation

  • The indole ring plane is nearly perpendicular to the benzofuran ring system, with a dihedral angle of 85.77 (2)

  • Vilazodone binds with high affinity to the serotonin re-uptake site but not to the norepinephrine or dopamine reuptake site

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Summary

Chemical context

Major depression disorder (MDD) currently ranks as the world’s fourth greatest cause of illness and is expected to rank second by the year 2020 according to WHO studies The title compound, viladozone hydrochloride (marketed as Viibryd by Forest Pharmaceuticals), is a new treatment option for MDD. It was approved on January 21, 2011 by the FDA, licensed by Merck KGaA. Vilazodone hydrochloride is a selective serotonin re-uptake inhibitor (SSRI) with properties that are most similar to those of citalopram, escitalopram (levapro), fluoveline, proxetin, and sertraline. The mechanism of the antidepressant effect of vilazodone is thought to be related to its enhancement of serotonergic activity in the CNS through selective inhibition of serotonin re-uptake. Vilazodone potently and selectively inhibits the re-uptake of serotonin (Choi et al, 2012; Reed et al, 2012; Schwartz & Singh, 2012). H atoms are shown as small circles of arbitrary radii

Structural commentary
Supramolecular features
Refinement
Full Text
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