Enciprazine


Enciprazine is an anxiolytic and antipsychotic of the phenylpiperazine class which was never marketed. It shows high affinity for the α1-adrenergic receptor and 5-HT1A receptor, among other sites. The drug was initially anticipated to produce ortho-methoxyphenylpiperazine, a serotonin receptor agonist with high affinity for the 5-HT1A receptor, as a significant active metabolite, but subsequent research found this not to be the case.

Synthesis

3,4,5-trimethoxyphenol is alkylated with epichlorohydrin to give oxirane . Opening of the epoxide with o-anisyl-piperazine completes the synthesis of enciprazine.