(S)-α-(Hydroxymethyl)benzeneacetic acid (1β,2α,4α,5β,7α)-9-butyl-9-methyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane-7-yl ester

Butylscopolamine,China Pharm

ChEBI: Butylscopolamine is a carboxylic ester resulting from the formal condensation of the carboxy group of (2S)-3-hydroxy-2-phenylpropanoic acid with the hydroxy group of (2R,4S,5S,7s)-9-butyl-7-hydroxy-9-methyl-3-oxa-9-azoniatricyclo[3.3.1.0(2,4)]nonane. It has a role as a muscarinic antagonist and an antispasmodic drug. It is a carboxylic ester, an epoxide, a quaternary ammonium ion and a tropane alkaloid.

1300 g of scopolamine base and 350 g of n-butylbromide in 600 ml acetonitrile is heated at 65°C for 160 hours. The oil obtained is dissolved in methanol. The solution is cooled and crystalline scopolamine N-n-butylbromide is filtered. After recrystallization from methanol was obtained scopolamine N-n-butylbromide with melting point 142-144°C and [α]d 20 = -20.5° (3% solution in water); yield 65%.

Anticholinergic, Spasmolytic, Antitussive