Abstract

Abstract A spectroscopic (ultraviolet, infrared and nuclear magnetic resonance) study of N-[(2-benzylmethylaminp)propyl]propionanilide hydrochloride is reported and probable conformations of this molecule (in which the phenyl group and amide function are non-planar, the protonated basic centre lies close to the amido-nitrogen atom, and the secondary methyl group is removed from the region above the aromatic plane) proposed on the basis of the spectroscopic results. Differences in analgesic stereospecificity and basic group structure between enantiomorphs of methadone and N-[(2-benzylmethylamino)propyl]propionanilide are discussed in terms of the probable conformations of the two analgesics.

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