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We previously reported that (+)-matrine and (+)-allomatrine have antinociceptive properties mediated mainly through the activation of kappa-opioid receptors. 1-Acyl-4-dialkylaminopiperidines were synthesized as the simplest derivatives of matrine, and the structure-activity relations were examined by the acetic acid-induced abdominal contraction test. The antinociceptive potencies of 1-alkyl-4-dialkylaminopiperidines were significantly lower than those of the corresponding 1-acyl-4-dialkylaminopiperidines. These findings suggest that the amide group of (+)-matrine is an essential functional group that influences antinociceptive potency.

biological and pharmaceutical bulletin

Antinociceptive Effects of 1-Acyl-4-dialkylaminopiperidine and 1-Alkyl-4-dialkylaminopiperidine in Mice: Structure-Activity Relation Study of Matrine-Type Alkaloids.