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Hydrogen bonding and anesthetic potency

S Yokono, D D Shieh, H Goto

    Journal of Medicinal Chemistry
    |July 1, 1982
    PubMed
    Summary
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    Potent inhalation anesthetics with weaker hydrogen bonds are more effective. This study measured hydrogen bond strengths using proton chemical shifts, correlating them with anesthetic potency.

    Area of Science:

    • Analytical Chemistry
    • Medicinal Chemistry
    • Physical Chemistry

    Background:

    • Inhalation anesthetics are crucial for surgical procedures.
    • Understanding the physicochemical properties of anesthetics is key to optimizing their clinical use.
    • Hydrogen bonding plays a significant role in molecular interactions and biological activity.

    Purpose of the Study:

    • To quantitatively compare the relative polar character of potent inhalation anesthetics.
    • To investigate the relationship between hydrogen bond strength and anesthetic potency.
    • To elucidate the role of hydrogen bonding in the mechanism of action of inhalation anesthetics.

    Main Methods:

    • Proton magnetic resonance spectroscopy was employed to measure proton chemical shifts.

    Related Experiment Videos

  • Hydrogen bond strengths were determined by analyzing chemical shift differences in cyclohexane and methanol.
  • The hydrogen bond shift (delta ppm) was calculated as the difference between infinitely diluted unassociated and hydrogen-bonded anesthetic chemical shifts.

    • Main Results:

    • Hydrogen bond shifts (in delta ppm) were measured for methoxyflurane (0.72), chloroform (0.75), halothane (1.06), isoflurane (1.38), and enflurane (1.44).
    • A strong correlation was observed between the measured hydrogen bond shifts and the clinical potencies (minimum alveolar concentration in man) of these anesthetics.
    • The data indicate that anesthetics forming weaker hydrogen bonds exhibit greater potency.

    Conclusions:

    • Acidic halogenated inhalation anesthetics demonstrate increased potency with weaker hydrogen bond formation.
    • Hydrogen bond strength is a critical factor influencing the clinical efficacy of inhalation anesthetics.
    • This study provides quantitative insights into the structure-activity relationship of anesthetic agents.