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Buprenorphine.

Jaroslaw Mazurek1, Marcel Hoffmann1, Anna Fernandez Casares1

  • 1Crystallics B.V., Meibergdreef 31, 1105 AZ Amsterdam, The Netherlands.

Acta Crystallographica. Section E, Structure Reports Online
|June 19, 2014
PubMed
Summary

The crystal structure of buprenorphine reveals a disordered cyclo-propyl-methyl group and specific hydrogen bonding. These interactions influence how buprenorphine molecules arrange in a zigzag chain formation.

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Area of Science:

  • Pharmacology
  • Crystallography
  • Organic Chemistry

Background:

  • Buprenorphine is a semi-synthetic opioid medication used for pain management and opioid use disorder treatment.
  • Understanding its crystal structure is crucial for comprehending its physical properties and potential interactions.

Purpose of the Study:

  • To elucidate the detailed crystal structure of buprenorphine.
  • To identify key intermolecular interactions, such as hydrogen bonding and molecular packing.

Main Methods:

  • Single-crystal X-ray diffraction analysis was performed on buprenorphine.
  • The crystal structure was solved and refined to determine atomic positions and bonding.

Main Results:

  • The cyclo-propyl-methyl group exhibited disorder over two sites, with a major component occupancy of 0.611(3).

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  • An intramolecular hydrogen bond was observed involving one hydroxyl group.
  • The other hydroxyl group participated in an intermolecular hydrogen bond, forming zigzag chains along the b axis.

    • Conclusions:

    • The crystal structure provides a detailed molecular-level understanding of buprenorphine.
    • Hydrogen bonding plays a significant role in the self-assembly and crystal packing of buprenorphine molecules.
    • This structural information can inform drug design and formulation strategies.