60-46-8

Centrine,Bristol,US,1953

Aminopentamide Sulfate affects gastric function and gastroduodenal ulcus. Used in the treatment of vomiting, diarrhea and other side effects in dogs/cats.

ChEBI: 4-(dimethylamino)-2,2-diphenylpentanamide is a diarylmethane.

A mixture of 14 g (0.05 mol) of α,α-diphenyl-γ-dimethylaminovaleronitrile, 16 g (0.2 mol) of sodium acetate, 14 g (0.2 mol) of hydroxylamine hydrochloride and 75 ml of ethyl alcohol was refluxed 18 hours. The mixture was cooled, poured into water and neutralized with ammonium hydroxide. The heavy white precipitate solidified on standing. The material was filtered and recrystallized from isopropanol. After three recrystallizations the aminopentamide product melted at 177° to 179°C.
The product is often used as the acid sulfate which is produced as follows: 252.0 g (0.85 mol) of α,α-diphenyl-γ-dimethylaminovaleronitrile was dissolved in one liter of isopropanol, and 70 ml of concentrated sulfuric acid was added as rapidly as possible. The mixture was heated until clear, then filtered and diluted with 1,500 ml of anhydrous ethyl acetate. The solution was cooled and filtered, and the white crystalline product was dried in vacuum over P2O5.

Anticholinergic

Crystallise dimevamide from aqueous EtOH. The hydrochloride forms leaflets from EtOH/Et2O with m 190-191o and is deliquescent. The picrate has m 210-211o. It is an antispasmotic. [Moffett et al. J Am Chem Soc 79 4451, 4457 1957, Beckett J Pharm Pharmacol 8 848 1956, Beilstein 14 III 1363, 14 IV 1865.]