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Methyl-ergometrine maleate from synchrotron powder diffraction data.

Jan Rohlíček, Michal Hušák, Bohumil Kratochvíl

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study details the crystal structure of 9,10-didehydro-N-[1-(hydroxy-meth-yl)prop-yl]-d-lysergamide maleate. Intermolecular hydrogen bonds create a 3D network, stabilizing the crystal structure of this ergolene derivative.

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    Area of Science:

    • Medicinal Chemistry
    • Crystallography
    • Organic Chemistry

    Background:

    • Ergolene derivatives are known for diverse pharmacological activities.
    • Understanding the solid-state structure is crucial for drug design and development.
    • The specific compound 9,10-didehydro-N-[1-(hydroxy-meth-yl)prop-yl]-d-lysergamide maleate has not been previously characterized in detail.

    Purpose of the Study:

    • To elucidate the crystal structure of 9,10-didehydro-N-[1-(hydroxy-meth-yl)prop-yl]-d-lysergamide maleate.
    • To analyze the intermolecular interactions within the crystal lattice.
    • To provide insights into the structural features of ergolene derivatives.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.

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  • The crystal structure was solved and refined using standard crystallographic software.
  • Analysis of bond lengths, bond angles, and intermolecular interactions was performed.

    • Main Results:

    • The crystal structure of 9,10-didehydro-N-[1-(hydroxy-meth-yl)prop-yl]-d-lysergamide maleate was successfully determined.
    • The compound features a rigid ergolene core with an indole plane, a six-membered carbon ring in an envelope conformation, and an equatorial methyl group on the N-methyl-tetra-hydro-pyridine ring.
    • An extensive three-dimensional hydrogen-bonding network involving N-H⋯O, O-H⋯N, and O-H⋯O interactions was observed, linking cations and anions.

    Conclusions:

    • The crystal structure provides a detailed understanding of the molecular conformation and solid-state arrangement of this ergolene derivative.
    • The identified hydrogen-bonding network plays a significant role in stabilizing the crystal structure.
    • These findings contribute to the structural knowledge of ergolene compounds and may inform future drug discovery efforts.