Cimemoxin
Cimemoxin, or cyclohexylmethylhydrazine, is a hydrazine monoamine oxidase inhibitor antidepressant which was never marketed.
Synthesis
It possesses 50 times the relative activity of iproniazid and 25x nialamide.3-Cyclohexene-1-carbaldehyde is reacted with N-acetylhydrazine to give the hydrazone, which is reduced by catalytic hydrogenation. The acetyl group is removed by acid hydrolysis.