# New Molecular Insights on Gabapentin

## TL;DR

Scientists studied gabapentin's structure in gas form and found five stable shapes that might explain how it works differently from GABA.

## Contribution

The study reveals new conformational and interaction patterns in gabapentin compared to GABA.

## Key findings

- Five stable conformers of gabapentin were detected with different intramolecular interactions.
- The equatorial form of gabapentin's cyclohexane ring is more abundant than the axial form.
- Gabapentin's conformational behavior differs significantly from GABA, possibly explaining their differing mechanisms of action.

## Abstract

Neutral gabapentin
has been vaporized by laser ablation and supersonically
expanded to record its rotational spectrum using Fourier transform
microwave spectroscopy. We report the detection of five stable conformers,
which differ in the intramolecular interactions between the different
functional groups (OH, C=O, and NH). Two configurations, axial and equatorial, are possible depending on the chair
form of the cyclohexane ring, and both forms are detected, with the
latter being predominant. The conformational landscape of gabapentin
is compared with that of GABA, and significant differences are observed.
One of the most meaningful results of such a comparison is that the
relationship between the intramolecular interactions and the relative
abundance within each type is reversed from GABA to gabapentin. It
could explain the distinction in the mechanism of action of GABA and
gabapentin, despite being structurally similar.