Abstract
Vortioxetine, C18H22N2S, (1), systematic name 1-{2-[(2,4-di-methyl-phen-yl)sulfan-yl]phen-yl}piperazine, a new drug used to treat patients with major depressive disorder, has been crystallized as the free base and its methanol monosolvate, C18H22N2S·CH3OH, (2). In both structures, the vortioxetine mol-ecules have similar conformations: in (1), the dihedral angle between the aromatic rings is 80.04 (16)° and in (2) it is 84.94 (13)°. The C-S-C bond angle in (1) is 102.76 (14)° and the corresponding angle in (2) is 103.41 (11)°. The piperazine ring adopts a chair conformation with the exocyclic N-C bond in a pseudo-equatorial orientation in both structures. No directional inter-actions beyond normal van der Waals contacts could be identified in the crystal of (1), whereas in (2), the vortioxetine and methanol mol-ecules are linked by N-H⋯O and O-H⋯N hydrogen bonds, generating [001] chains.
Highlights
102.76 (14) and the corresponding angle in (2) is 103.41 (11)
No directional interactions beyond normal van der Waals contacts could be identified in the crystal of (1), whereas in (2), the vortioxetine and methanol molecules are linked by N—H O and
The medications most often prescribed for depression include the selective serotonin reuptake inhibitors (SSRIs) and the serotonin norepinephrine reuptake inhibitors (SNRIs)
Summary
Major depressive disorder (MDD) is a disabling mental illness responsible for almost 66 million disability-adjusted life-years globally (Bidzan et al, 2012). As several neurotransmitter pathways may be involved in MDD, antidepressants possessing two or more complementary modes of action (i.e. multimodal) have been a focus of MDD therapy for some time (Richelson, 2013). Vortioxetine is an investigational multi-modal antidepressant that is believed to work through a combination of two pharmacological modes of action: serotonin (5-HT). The piperazine ring of both structures adopts a chair conformation with the exocyclic N1—C14 bond in a pseudo equatorial orientation. The molecular structure of compound (1), showing 50% probability displacement ellipsoids
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