Mefeclorazine

Mefeclorazine (INNTooltip International Nonproprietary Name) is a neuroleptic (antipsychotic) of the phenethylamine and arylpiperazine groups.^[1][2][3]

CAS Number

• 1243-33-0

PubChem CID

• 3064105

ChemSpider

• 2324598

UNII

• IM840F32VV

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Mefeclorazine

Identifiers
IUPAC name 1-(2-chlorophenyl)-4-[2-(3,4-dimethoxyphenyl)ethyl]piperazine
CAS Number	1243-33-0
PubChem CID	3064105
ChemSpider	2324598
UNII	IM840F32VV
ChEMBL	ChEMBL2107173
CompTox Dashboard (EPA)	DTXSID30154262
Chemical and physical data
Formula	C20H25ClN2O2
Molar mass	360.88 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=C(C=C(C=C1)CCN2CCN(CC2)C3=CC=CC=C3Cl)OC
InChI InChI=1S/C20H25ClN2O2/c1-24-19-8-7-16(15-20(19)25-2)9-10-22-11-13-23(14-12-22)18-6-4-3-5-17(18)21/h3-8,15H,9-14H2,1-2H3 Key:PJDRMPCBIWKBJA-UHFFFAOYSA-N

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Part of mefeclorazine's chemical structure is based on 3,4-dimethoxyphenethylamine (DMPEA or homoveratrylamine), which has structural similarity to the neurotransmitter dopamine.^[1] Mefeclorazine was invented by Jack Mills of Eli Lilly in 1958.^[4] Although it is not known to have ever been used clinically,^[1] it is based on a chemically rational synthetic design.

The ortho-chlorophenylpiperazine (oCPP) moiety forms part of the molecular structure.^[1] This precursor finds dual use in the synthesis of the arylpiperazines enpiprazole and KMUP-1.^{[citation needed]}