Enciprazine

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. 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] (1) is alkylated with epichlorohydrin (2) to give [(3,4,5-Trimethoxyphenoxy)methyl]oxirane [74760-14-8] (3). Opening of the epoxide with o-anisyl-piperazine [35386-24-4] (4) completes the synthesis of enciprazine (5).