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1H and 13C NMR studies on the antidepressant drug tianeptine

✍ Scribed by N. Platzer; J. P. Bouchet; C. Malen; C. Labrid; E. Mocaer

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
667 KB
Volume
30
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The conformational behaviour of 7‐[(3‐chloro‐6,11‐dihydro‐6‐methyldibenzo[c, f][1,2]thiazepin‐11‐yl)amino] heptanoic acid 5,5 dioxide (tianeptine), a new antidepressant drug, was studied by means of ^1^H and ^13^C NMR. The ring skeleton exhibits two distinct conformations at low temperature. The conformational exchange is still restricted at room temperature, particularly in the solvents D~2~O and CDCl~3~, where significant aggregation of the molecules occurs. The side‐chain seems to adopt a preferential conformation where it is bent over the unsubstituted aromatic ring. This conformational preference in the biologically active structure might be related to the observed loss of activity when substituents are introduced on the aromatic rings.

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