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Related Experiment Videos

(-)-Norcocaine

N Zhu1, M Reynolds, C L Klein

  • 1Department of Chemistry, Xavier University of Louisiana, New Orleans 70125.

Acta Crystallographica. Section C, Crystal Structure Communications
|December 15, 1994
PubMed
Summary
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This study details a cocaine metabolite, methyl 3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate. Its rigid structure, with flexible substituents, was determined through crystallization.

Area of Science:

  • Organic Chemistry
  • Pharmacology
  • Crystallography

Background:

  • Cocaine is a tropane alkaloid with significant abuse potential.
  • Metabolism of cocaine produces various compounds, including ester derivatives.
  • Understanding cocaine metabolites is crucial for forensic science and toxicology.

Purpose of the Study:

  • To characterize the structure of a specific cocaine metabolite.
  • To elucidate the conformational properties of this tropane alkaloid derivative.
  • To provide crystallographic data for [2R,3S-(2 beta,3 beta)]-methyl 3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate.

Main Methods:

  • Single crystal X-ray diffraction analysis.
  • Crystallization of the compound as a free base.

Related Experiment Videos

  • Conformational analysis of the bicyclic system and substituents.

    • Main Results:

    • The title compound, C16H19NO4, was successfully crystallized.
    • The piperidine ring adopted a chair conformation.
    • The tropane ring system, methoxycarbonyl, and benzoyl groups exhibited rigidity, with limited rotational flexibility in substituents.

    Conclusions:

    • The crystallographic data provides a precise three-dimensional structure of the cocaine metabolite.
    • The conformational rigidity of the core structure influences its chemical and biological properties.
    • This detailed structural information aids in understanding cocaine metabolism and the pharmacology of its derivatives.