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Title: /sup 13/C NMR studies of the molecular flexibility of antidepressants

Abstract

The solution dynamics of a series of clinically potent antidepressants have been investigated by measuring /sup 13/C NMR relaxation parameters. Correlation times and internal motional rates were calculated from spin-lattice relaxation times and nuclear Overhauser effects for the protonated carbons in mianserin, imipramine-like antidepressants, and amitriptyline-like antidepressants. These data were interpreted in terms of overall molecular tumbling, internal rotations, and inherent flexibility of these structures. Of particular interest was the conformational variability of the tricyclic nucleus of the tricyclic antidepressants, where the data indicated a fivefold difference in mobility of the dimethylene bridge of imipramine-like antidepressants relative to amitriptyline-like compounds. The implications of such a difference in internal motions is discussed in relation to previous NMR studies and to the reported differences in pharmacological activity of these antidepressants.

Authors:
; ; ;
Publication Date:
Research Org.:
Victorian College of Pharmacy, Ltd., Parkville, Australia
OSTI Identifier:
5811221
Resource Type:
Journal Article
Resource Relation:
Journal Name: J. Pharm. Sci.; (United States); Journal Volume: 2
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; ANTIDEPRESSANTS; MOLECULAR STRUCTURE; CARBON 13; FLEXIBILITY; NUCLEAR MAGNETIC RESONANCE; OVERHAUSER EFFECT; SOLVENTS; SPIN-LATTICE RELAXATION; TRACER TECHNIQUES; WATER; CARBON ISOTOPES; CENTRAL NERVOUS SYSTEM AGENTS; DRUGS; EVEN-ODD NUCLEI; HYDROGEN COMPOUNDS; ISOTOPE APPLICATIONS; ISOTOPES; LIGHT NUCLEI; MAGNETIC RESONANCE; MECHANICAL PROPERTIES; NUCLEI; OXYGEN COMPOUNDS; PSYCHOTROPIC DRUGS; RELAXATION; RESONANCE; STABLE ISOTOPES; TENSILE PROPERTIES; 550201* - Biochemistry- Tracer Techniques

Citation Formats

Munro, S.L., Andrews, P.R., Craik, D.J., and Gale, D.J. /sup 13/C NMR studies of the molecular flexibility of antidepressants. United States: N. p., 1986. Web. doi:10.1002/jps.2600750206.
Munro, S.L., Andrews, P.R., Craik, D.J., & Gale, D.J. /sup 13/C NMR studies of the molecular flexibility of antidepressants. United States. doi:10.1002/jps.2600750206.
Munro, S.L., Andrews, P.R., Craik, D.J., and Gale, D.J. Sat . "/sup 13/C NMR studies of the molecular flexibility of antidepressants". United States. doi:10.1002/jps.2600750206.
@article{osti_5811221,
title = {/sup 13/C NMR studies of the molecular flexibility of antidepressants},
author = {Munro, S.L. and Andrews, P.R. and Craik, D.J. and Gale, D.J.},
abstractNote = {The solution dynamics of a series of clinically potent antidepressants have been investigated by measuring /sup 13/C NMR relaxation parameters. Correlation times and internal motional rates were calculated from spin-lattice relaxation times and nuclear Overhauser effects for the protonated carbons in mianserin, imipramine-like antidepressants, and amitriptyline-like antidepressants. These data were interpreted in terms of overall molecular tumbling, internal rotations, and inherent flexibility of these structures. Of particular interest was the conformational variability of the tricyclic nucleus of the tricyclic antidepressants, where the data indicated a fivefold difference in mobility of the dimethylene bridge of imipramine-like antidepressants relative to amitriptyline-like compounds. The implications of such a difference in internal motions is discussed in relation to previous NMR studies and to the reported differences in pharmacological activity of these antidepressants.},
doi = {10.1002/jps.2600750206},
journal = {J. Pharm. Sci.; (United States)},
number = ,
volume = 2,
place = {United States},
year = {Sat Feb 01 00:00:00 EST 1986},
month = {Sat Feb 01 00:00:00 EST 1986}
}