Alpertine

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;

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.

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

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. Oxypertine, milipertine, and solypertine all antagonize the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals. Conversely however, alpertine was not effective, at least at doses of up to 10 mg/kg. ortho-Methoxyphenylpiperazine (oMeOPP) has been said to be a metabolite of the related drugs milipertine and oxypertine.

Alpertine was first described in the scientific literature by 1971.