Analgesically active basic anilides: stereospecificity and structure of the basic group

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Abstract
The synthesis of (RS)-, (R)- and (S)-N-(2-dimethylaminopropyl)propionanilide and the benzylmethylamino- analogues of methadone and isomethadone is described. The hot-plate activities in mice of the (S)- enantiomorphs of both the dimethylamino- and benzylmethylaminopropionanilides are greater than those of the corresponding (RS)- and (R)- forms, while the methadone and isomethadone analogues are inactive in the same test. These results support the view that 3-amino-1,1-diphenylpropyl- and basic anilide - analgesics differ in their modes of binding to the analgesic receptor site.