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Selectivity of Sterically Fixed Tryptamine and 5‐Methoxytryptamine Derivatives for Serotonin Receptor Subtypes, I: Synthesis of N ‐Alkyl‐ and N,N ‐Dialkyl‐3‐indolylbicyclo[2.2.1]heptane‐2‐amines
Author(s) -
Rehse Klaus,
Zimmermann Hans
Publication year - 1994
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19943270203
Subject(s) - tryptamine , chemistry , tryptamines , stereochemistry , ethylamine , serotonin , heptane , selectivity , receptor , organic chemistry , biochemistry , catalysis
Twenty‐six title compounds with the ethylamine part of tryptamine or 5‐methoxytryptamine fixed in an anticlinal ecliptic conformation were synthesized for assaying them at the different known serotonin receptors. Several alkylation methods have been improved and adapted for the space consuming norbornane system. The structures were fully elucidated by high‐field NMR spectroscopy. All 1 H‐ and 13 C‐signals could be assigned by means of 1 H‐ 1 H‐ and 13 C‐ 1 H‐correlation spectroscopy (COSY).