Quinuclidine chemistry. 4. Diuretic properties of cis-3-amino-2-benzhydrylquinuclidine

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Abstract
A number of 3-amino-2-benzhydrylquinuclidines were tested for diuretic activity in both rats and dogs. The Schiff base formed from 2-benzhydryl-3-quinuclidinone and benzylamine was reduced with NaBH4 to a mixture of isomers, the cis isomer being preponderants. cis-2-Benzhydryl-3-benzylaminoquinuclidine was isolated by chromatography and debenzylat:d to cis-3-amino-2-benzhydrylquinuclidine, the most active compound in this series. The corresponding trans isomer was considerably less active. It was made by reacting the mesylate of cis-2-benzhydr-l-3-quinuclidinol with Nan3 to form trans-3-azido-2-benzhydrylquinuclidine which was reduced with LiAlH4. In dose-response studies (sodium excretion as a function of dose) in rats the maximal or ceiling effect of cis-3-amino-2-benzhydrylquinuclidine was considerably greater than that of hydroflumethiazide but less than that of furosemide. An unusual biphasic dose-response was seen in dogs with cis-3-amino-2-bezhydrylquinuclidine, centering around 10 mg/kg.

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