Issue 30, 2021

An examination of the relationship between molecular dipole moment and blood-gas partition for common anaesthetic gases

Abstract

The solubility of inhalational anaesthetics in the bloodstream is related to the minimum alveolar concentration (MAC), which is an indicator of anaesthetic gas potency. The blood-gas partition coefficient (Kbg) is a measure of how much anaesthetics bind to plasma proteins in the blood compared to air. Just like the octanol–water partition coefficient, the Kbg may be related to the molecular dipole moment (μ), which can be modulated by the molecular conformation. Our quantum-chemical calculations demonstrated that subtle stereoelectronic interactions, namely those responsible for the anomeric and gauche effects, control the conformational equilibrium of some widely used volatile fluorinated anaesthetics and, consequently, of their molecular dipole moments. Since a remarkable correlation between empirical Kbg and calculated μ was found for these anaesthetics, the average molecular dipole moments may be used to predict the anaesthetic gas potency and other properties, such as lipid solubility, of inhalational anaesthetic analogs.

Graphical abstract: An examination of the relationship between molecular dipole moment and blood-gas partition for common anaesthetic gases

Supplementary files

Article information

Article type
Paper
Submitted
02 juin 2021
Accepted
14 juil. 2021
First published
14 juil. 2021

Org. Biomol. Chem., 2021,19, 6665-6670

An examination of the relationship between molecular dipole moment and blood-gas partition for common anaesthetic gases

F. A. Martins and M. P. Freitas, Org. Biomol. Chem., 2021, 19, 6665 DOI: 10.1039/D1OB01067K

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