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

We previously reported that (+)-matrine and (+)-allomatrine have antinociceptive properties mediated mainly through the activation of κ-opioid receptors. 1-Acyl-4-dialkylaminopiperidines were synthesized as the simplest derivatives of matrine, and the structure–activity relations were examined by th...

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Bibliographic Details
Published in:Biological & pharmaceutical bulletin 2002, Vol.25(8), pp.1030-1034
Main Authors: Kobashi, Seiichi, Kubo, Hajime, Yamauchi, Takayasu, Higashiyama, Kimio
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - pharmacology
Analgesics
Analgesics - chemistry
Analgesics - pharmacology
Animals
antinociception
Biological and medical sciences
Dose-Response Relationship, Drug
General pharmacology
Male
matrine
Medical sciences
Mice
Mice, Inbred ICR
Neuropharmacology
Pain Measurement - drug effects
Pain Measurement - methods
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Piperidines - chemistry
Piperidines - pharmacology
Quinolizines
Structure-Activity Relationship
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Summary:We previously reported that (+)-matrine and (+)-allomatrine have antinociceptive properties mediated mainly through the activation of κ-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.
ISSN:0918-6158
1347-5215
DOI:10.1248/bpb.25.1030