Biomaterial Database

Quinuclidine chemistry. 4. Diuretic properties of cis-3-amino-2-benzhydrylquinuclidine. 1975

E J Warawa, and N J Mueller

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.

UI	MeSH Term	Description	Entries
D011188	Potassium	An element in the alkali group of metals with an atomic symbol K, atomic number 19, and atomic weight 39.10. It is the chief cation in the intracellular fluid of muscle and other cells. Potassium ion is a strong electrolyte that plays a significant role in the regulation of fluid volume and maintenance of the WATER-ELECTROLYTE BALANCE.
D011812	Quinuclidines	A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.	Quinuclidine
D002712	Chlorides	Inorganic compounds derived from hydrochloric acid that contain the Cl- ion.	Chloride,Chloride Ion Level,Ion Level, Chloride,Level, Chloride Ion
D004231	Diuresis	An increase in the excretion of URINE. (McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed)	Diureses
D004232	Diuretics	Agents that promote the excretion of urine through their effects on kidney function.	Diuretic,Diuretic Effect,Diuretic Effects,Effect, Diuretic,Effects, Diuretic
D004285	Dogs	The domestic dog, Canis familiaris, comprising about 400 breeds, of the carnivore family CANIDAE. They are worldwide in distribution and live in association with people. (Walker's Mammals of the World, 5th ed, p1065)	Canis familiaris,Dog
D004305	Dose-Response Relationship, Drug	The relationship between the dose of an administered drug and the response of the organism to the drug.	Dose Response Relationship, Drug,Dose-Response Relationships, Drug,Drug Dose-Response Relationship,Drug Dose-Response Relationships,Relationship, Drug Dose-Response,Relationships, Drug Dose-Response
D005665	Furosemide	A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.	Frusemide,Fursemide,Errolon,Frusemid,Furanthril,Furantral,Furosemide Monohydrochloride,Furosemide Monosodium Salt,Fusid,Lasix
D006857	Hydroflumethiazide	A thiazide diuretic with actions and uses similar to those of HYDROCHLOROTHIAZIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p822)	Diucardin,Trifluoromethylhydrothiazide
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia