Lomevactone (

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; developmental code name DR-250) is a drug described as a psychostimulant and antidepressant which was chemical synthesis, synthesized and assayed in the 1980s, but was never marketed.

Stereoisomers

There are eight possible stereoisomers of lomevactone. It is the (3''R'',4''R'',6''R'')-form that has the psychotherapeutic properties. :

Synthesis

The conjugate 1,4-alkylation reaction between 4-chlorobenzylideneacetone (1) and phenylacetonitrile (2) gives 3-(4-chlorophenyl)-5-oxo-2-phenylhexanenitrile (3). The selective reduction of the keto group to the alcohol with sodium borohydride gives 3-(4-chlorophenyl)-5-hydroxy-2-phenylhexanenitrile (4). Hydrolysis of the nitrile to an acid gives 3-(4-chlorophenyl)-5-hydroxy-2-phenylhexanoic acid. This is followed by lactone formation completing the synthesis of lomevactone (5). Lomevactone synthesis

References

2-Pyrones Antidepressants 4-Chlorophenyl compounds Stimulants Abandoned drugs {{nervous-system-drug-stub