SYNTHESIS OF QUATERNARY AMMONIUM SALTS AND N-OXIDES OF ANISODAMINE AND ANISODINE

In order to search for effective peripheral anticholinic atropine type drugs, Nmethylbromides(Ⅴ-Ⅵ), N-methylmethosulfates (Ⅸ and Ⅹ) and N-oxides (ⅩⅣ and ⅩⅤ) of anisodamine and anisodine were prepared. In exploring stronger musculotropic organic antispasmodics, n-butyl bromide derivatives of both alkaloids were also prepared (Ⅺ and Ⅻ). Deoxyanisodine (Ⅲ) was obtained as a minor product on hydrogenation of anisodine. Physical and NMR spectral data of these derivatives and related compounds were listed in tables 1 and 2 respectively. The anticholinic screening results showed that N-methyl bromide quaternary ammonium salts were more active than their parent compounds. Among them anisodamine-N-methyl bromide (Ⅴ) is the most active.