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Venlafaxine besylate monohydrate.

Carolina H Corvalan¹, Daniel R Vega²

¹Gerencia Materiales, GAEN - CAC - CNEA, Av. Gral. Paz 1499, (1650) San Martín, Buenos Aires, Argentina.

Acta Crystallographica. Section E, Structure Reports Online

|January 24, 2014

Summary

This study details the crystal structure of venlafaxine besylate salt hydrate. It reveals a unique closed conformation of the venlafaxine cation stabilized by intramolecular hydrogen bonding.

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Area of Science:

Crystallography
Medicinal Chemistry
Solid-State Chemistry

Background:

Venlafaxine is a widely used antidepressant.
Understanding the solid-state properties of drug salts is crucial for formulation and stability.
Besylate salts are common pharmaceutical forms.

Purpose of the Study:

To characterize the crystal structure of venlafaxine besylate salt hydrate.
To investigate the intermolecular interactions and crystal packing.
To identify novel conformational features of the venlafaxine cation.

Main Methods:

Single-crystal X-ray diffraction analysis.
Hydrogen bond analysis (graph set notation).
Analysis of non-covalent interactions (C-H···O, C-H···π).

Main Results:

The crystal structure comprises venlafaxine cations, besylate anions, and water molecules.
Besylate anions and water molecules form hydrogen-bonded dimers.
The crystal packing exhibits a chain of dimers and cations linked by hydrogen bonds and other interactions.
A novel, closed conformation of the venlafaxine cation stabilized by an intramolecular N-H···O interaction was observed.

Conclusions:

The crystal structure provides detailed insights into the solid-state behavior of venlafaxine besylate.
The observed intramolecular interaction in the venlafaxine cation is a significant finding.
This structural information can aid in the development of improved pharmaceutical formulations.