Alpertine

Alpertine (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name; developmental code name WIN-31665) is a drug of the pertine group described as an antipsychotic, neuroleptic, and tranqulizer which was never marketed.^[1][2][3]

Other namesWIN31665; WIN-31,665; Win 31665

CAS Number

• 27076-46-6

PubChem CID

• 166547

ChemSpider

• 145751

Quick facts Clinical data, Other names ...

Alpertine

Clinical data
Other names	WIN31665; WIN-31,665; Win 31665
Identifiers
IUPAC name ethyl 5,6-dimethoxy-3-[2-(4-phenylpiperazin-1-yl)ethyl]-1H-indole-2-carboxylate
CAS Number	27076-46-6
PubChem CID	166547
ChemSpider	145751
UNII	KYT38QTB4K
KEGG	D02635
ChEBI	CHEBI:177808
ChEMBL	ChEMBL2104031
CompTox Dashboard (EPA)	DTXSID30181538
Chemical and physical data
Formula	C25H31N3O4
Molar mass	437.540 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCOC(=O)C1=C(C2=CC(=C(C=C2N1)OC)OC)CCN3CCN(CC3)C4=CC=CC=C4
InChI InChI=1S/C25H31N3O4/c1-4-32-25(29)24-19(20-16-22(30-2)23(31-3)17-21(20)26-24)10-11-27-12-14-28(15-13-27)18-8-6-5-7-9-18/h5-9,16-17,26H,4,10-15H2,1-3H3 Key:RXAVJRAUFOPBOO-UHFFFAOYSA-N

Close

Structurally, it is a substituted tryptamine and a piperazinylethylindole.^[4] The drug is closely structurally related to other "pertines" including milipertine, oxypertine, and solypertine, which are also tryptamines and piperazinylethylindoles.^[4]

The related drug oxypertine shows high affinity for the serotonin 5-HT₂ and dopamine D₂ receptors (K_i = 8.6 nM and 30 nM, respectively) and is also known to act as a catecholamine depleting agent.^[5][6] Oxypertine, milipertine, and solypertine all antagonize the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals.^[5][7] Conversely however, alpertine was not effective, at least at doses of up to 10 mg/kg.^[5][7] ortho-Methoxyphenylpiperazine (oMeOPP) has been said to be a metabolite of the related drugs milipertine and oxypertine.^[8][9]

Alpertine was first described in the scientific literature by 1971.^[1]