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(S)-(+)-Ketamine hydro-chloride.

Patrick Hakey¹, Wayne Ouellette, Jon Zubieta

¹Department of Chemistry, Syracuse University, Syracuse, New York 13244, USA.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

The crystal structure of (S)-(+)-ketamine hydrochloride, a potent anesthetic, was determined. Its chair conformation and hydrogen bonding network are key structural features.

Area of Science:

Crystallography
Medicinal Chemistry
Pharmacology

Background:

Ketamine is a widely used anesthetic known for its potent effects.
(S)-(+)-ketamine is significantly more potent than its R-isomer.
Understanding the crystal structure of ketamine hydrochloride is crucial for its pharmaceutical development.

Purpose of the Study:

To determine the crystal structure of (S)-(+)-ketamine hydrochloride.
To elucidate the conformational preferences and intermolecular interactions of the compound.
To provide insights into the structural basis for its anesthetic potency.

Main Methods:

Single-crystal X-ray diffraction at 90 K.
Analysis of molecular conformation and crystal packing.

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Identification of hydrogen bonding networks.

Main Results:

The crystal structure of (S)-(+)-ketamine hydrochloride (C(13)H(17)ClNO(+)·Cl(-)) was determined.
The cyclohexanone ring adopts a chair conformation with equatorial oxo group.
The methyl-amino group is equatorial, while the 2-chlorophenyl group is axial.
An infinite 1D hydrogen-bonding network involving chloride anions and protonated amine groups was observed.

Conclusions:

The determined crystal structure provides a detailed molecular and supramolecular understanding of (S)-(+)-ketamine hydrochloride.
The observed conformation and hydrogen bonding pattern likely contribute to the compound's stability and pharmacological activity.
This structural data can inform future drug design and development of related anesthetic agents.