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A series of 2-(tetrahydroisoquinolin-2-ylmethyl)- and 2-(isoindolin-2-ylmethyl)imidazolines were prepared and tested for alpha1- and alpha2-adrenoceptor affinity with radioligand binding. Several compounds, 5-fluoro- (5h), 5-chloro- (5j), 5,8-dimethoxy- (5r), and 5,8-dimethoxy-1-methyl- (5s) 2-(tetrahydroisoquinolin-2-ylmethyl)imidazoline, were found to be selective alpha2-adrenoceptor ligands on the basis of displacement of [3H]yohimbine from rat cerebral cortical membranes. One compound, 2-[(8-chloro tetrahydroisoquinolin-2-yl)methyl]imidazoline (5m), showed a 36-fold difference in affinity for the [3H]idazoxan-labeled alpha2-adrenoceptor relative to the [3H]yohimbine-labeled site, which may be evidence for alpha2-adrenoceptor subtypes.
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Reference：
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem