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Summary

This summary is machine-generated.

This study characterizes a degradation impurity of paroxetine hydrochloride hemihydrate (PAXIL), a selective serotonin reuptake inhibitor (SSRI) antidepressant. The impurity, a hydrochloride salt, exhibits a chair conformation with specific equatorial group positioning and forms hydrogen-bonded tapes.

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Area of Science:

Pharmaceutical Chemistry
Structural Chemistry
Medicinal Chemistry

Background:

Paroxetine hydrochloride hemihydrate (PAXIL) is a widely used selective serotonin reuptake inhibitor (SSRI) antidepressant.
Drug degradation impurities can impact the safety and efficacy of pharmaceutical products.
Understanding the structure of impurities is crucial for quality control and regulatory compliance.

Purpose of the Study:

To characterize the chemical structure and solid-state properties of a specific degradation impurity of paroxetine hydrochloride hemihydrate.
To elucidate the intermolecular interactions and crystal packing of the title compound.

Main Methods:

Chemical synthesis and isolation of the degradation impurity.
Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.
Spectroscopic methods for structural confirmation (implied).

Main Results:

The title compound, C(12)H(17)FNO(+)·Cl(-), was identified as a degradation impurity of paroxetine.
The impurity exists as a hydrochloride salt, with protonation on the piperidine ring.
The piperidinium ring adopts a chair conformation, with hydroxy-methyl and 4-fluorophenyl groups in equatorial positions.
Charge-assisted N(+)-H⋯Cl(-) hydrogen bonds form tapes along the b axis, connected by O-H⋯Cl(-) hydrogen bonds along the a axis.

Conclusions:

The structural elucidation provides critical information about a paroxetine degradation product.
The observed hydrogen bonding network explains the crystal packing and stability of the impurity.
This characterization aids in the quality control of paroxetine formulations and understanding its degradation pathways.