enpiprazole

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 1-(2-Chlorophenyl)-4-[2-(1-methyl-1H-pyrazol-4-yl)ethyl]piperazine

| image = Enpiprazole.png

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 31729-24-5

| ATC_prefix = none

| ATC_suffix =

| PubChem = 208921

| ChEMBL = 2104269

| ChemSpiderID = 181017

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 78G92X9EH7

| C=16 | H=21 | Cl=1 | N=4

| smiles = Clc3ccccc3N2CCN(CCc1cn(nc1)C)CC2

}}

Enpiprazole (INN, BAN) is an anxiolytic drug of the phenylpiperazine group that was never marketed.{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA488|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=488–}}{{cite book | author = Bernan, British Pharmacopoeia Commission | title = British Approved Names 2002 | publisher = The Stationery Office | location = United Kingdom | year = 2002 | pages = 359 | isbn = 0-11-322558-X | url = https://books.google.com/books?id=zruxjioUFngC&pg=PA100}} It produces anxiolytic-like effects in animals, though these effects appear to be biphasic and may reverse at high doses.{{cite journal |vauthors=Murasaki M, Hara T, Oguchi T, Inami M, Ikeda Y | title = Action of enpiprazole on emotional behavior induced by hypothalamic stimulation in rats and cats | journal = Psychopharmacology | volume = 49 | issue = 3 | pages = 271–4 |date=September 1976 | pmid = 12526 | doi = 10.1007/BF00426829| s2cid = 10302402 }} It is known to produce ortho-chlorophenylpiperazine (oCPP) as a metabolite.{{cite book|author=B.L. Goodwin|title=Handbook of Biotransformations of Aromatic Compounds|url=https://books.google.com/books?id=luttauRomC8C&pg=SL3-PA124|date=10 November 2004|publisher=CRC Press|isbn=978-0-203-64196-5|pages=3–}}