Cericlamine
Cericlamine is a potent and moderately selective serotonin reuptake inhibitor of the amphetamine family that was investigated as an antidepressant for the treatment of depression, anxiety disorders, and anorexia nervosa by Jouveinal but did not complete development and was never marketed. It reached phase III clinical trials in 1996 before development was discontinued in 1999.Synthesis
Arylation of methacrylic acid with a diazonium salt of 3,4-dichloroaniline, is carried out according to the Meerwein reaction catalysed by a metallic halide. For the next step, the halide is displaced by dimethylamine, then esterification is performed, followed by reduction with a metal hydride.
