Synthesis of 1-substituted analogs of trimetoquinol possessing differential and selective .beta.-adrenergic properties

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Abstract
Trimetoquinol (1) is used as a bronchial relaxant and is known to possess potent .beta.1- and .beta.2-stimulant properties. The synthesis of the 1,1-disubstiuted tetrahydroisoquinoline analogs, 1-methyl-1-(3,4,5-trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (2) and 1-benzyl-1-(3,4,5-trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3), is described. The profile of .beta.-adrenergic activity for these analogs was determined and compared to that in isolated guinea pig atrial, tracheal and rat adipocyte preparations. Unexpected selective .beta.1-blocking activity in guinea pig trachea was noted with analog 3. With the exception of 2 in guinea pig atria, 2 and 3 did not possess any .beta.-stimulant activity. Substitution at the 1 position of 1 revealed qualitative differences in .beta.-adrenergic activity.

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