Enciprazine

Enciprazine
Clinical data
Other names	WY-48624; D-3112
Routes of; administration	Oral
Identifiers
	IUPAC name 1-[4-(2-Methoxyphenyl)piperazin-1-yl]-3-(3,4,5-trimethoxyphenoxy)propan-2-ol;
CAS Number	68576-86-3 ; 68576-88-5;
PubChem CID	50222;
ChemSpider	34991993;
UNII	L6X660925G;
KEGG	D13112;
ChEMBL	ChEMBL101284;
CompTox Dashboard (EPA)	DTXSID3057806 ;
Chemical and physical data
Formula	C23H32N2O6
Molar mass	432.517 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC=CC=C1N2CCN(CC2)CC(COC3=CC(=C(C(=C3)OC)OC)OC)O;
	InChI InChI=1S/C23H32N2O6/c1-27-20-8-6-5-7-19(20)25-11-9-24(10-12-25)15-17(26)16-31-18-13-21(28-2)23(30-4)22(14-18)29-3/h5-8,13-14,17,26H,9-12,15-16H2,1-4H3; Key:KSQCNASWXSCJTD-UHFFFAOYSA-N;

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.^[1]^[2]^[3]^[4] It shows high affinity for the α₁-adrenergic receptor and 5-HT_1A receptor, among other sites.^[3]^[5]^[6] The drug was initially anticipated to produce ortho-methoxyphenylpiperazine (oMeOPP), a serotonin receptor agonist with high affinity for the 5-HT_1A receptor, as a significant active metabolite, but subsequent research found this not to be the case.^[5]

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Synthesis