Introduction
Enciprazine (INN, BAN; enciprazine hydrochloride (USAN); developmental code names WY-48624, D-3112) is an anxiolytic and antipsychotic of the phenylpiperazine class which was never marketed.
Outline
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 (oMeOPP), 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 (aka Antiarol) [642-71-7] is alkylated with epichlorohydrin to give [(3,4,5-Trimethoxyphenoxy)methyl]oxirane [74760-14-8]. Opening of the epoxide with o-anisyl-piperazine [35386-24-4] completes the synthesis of enciprazine.
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