1-Allyl and 1-(3, 3-dimethylallyl) analogues of pethidine and its reversed ester

Abstract

Abstract The preparation of some 1-allyl and 1-(3, 3-dimethylallyl)-4-phenylpiperidines related to pethidine and its reversed ester is described and the hot-plate activities in mice of these compounds reported. All six derivatives displayed morphine-like properties in mice, four being more potent (1·5–6 times) than morphine, but failed to act as analgesic antagonists in rats. The results are contrasted with the properties of similarly N-substituted fused-ring analgesics and differences discussed in terms of drug-receptor interaction modes.