Reversed ester analogues of pethidine: isomeric 4-acetoxy-1,2,6-trimethyl-4-phenyrpiperidines

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Abstract
The preparation and stereochemical characterization of all three isomeric forms of 4-acetoxy-1,2,6-trimethyl-4-phenylpiperidine is described. Of these, only the t-2-Me,c-6-Me,r-4-OCOMe isomer was an effective analgesic in mice (2·3 × pethidine) as judged by the hot-plate test. The results, together with reported data, demonstrate the potency raising effects of axial methyl α- to nitrogen and the lowering action of equatorial α-methyl substituents in reversed esters of pethidine.