/sup 13/C NMR studies of the molecular flexibility of antidepressants
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.
- Research Organization:
- Victorian College of Pharmacy, Ltd., Parkville, Australia
- OSTI ID:
- 5811221
- Journal Information:
- J. Pharm. Sci.; (United States), Journal Name: J. Pharm. Sci.; (United States) Vol. 2; ISSN JPMSA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
59 BASIC BIOLOGICAL SCIENCES
ANTIDEPRESSANTS
CARBON 13
CARBON ISOTOPES
CENTRAL NERVOUS SYSTEM AGENTS
DRUGS
EVEN-ODD NUCLEI
FLEXIBILITY
HYDROGEN COMPOUNDS
ISOTOPE APPLICATIONS
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
MECHANICAL PROPERTIES
MOLECULAR STRUCTURE
NUCLEAR MAGNETIC RESONANCE
NUCLEI
OVERHAUSER EFFECT
OXYGEN COMPOUNDS
PSYCHOTROPIC DRUGS
RELAXATION
RESONANCE
SOLVENTS
SPIN-LATTICE RELAXATION
STABLE ISOTOPES
TENSILE PROPERTIES
TRACER TECHNIQUES
WATER