Milipertine

Milipertine
Clinical data
Other names	Millipertine; WIN18935; WIN-18,935; Win-18935
Identifiers
	IUPAC name 5,6-dimethoxy-3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2-methyl-1H-indole;
CAS Number	24360-55-2;
PubChem CID	32345;
ChemSpider	29982;
UNII	WX1V67H28T;
KEGG	D02673;
ChEMBL	ChEMBL2105252;
CompTox Dashboard (EPA)	DTXSID00179104 ;
Chemical and physical data
Formula	C24H31N3O3
Molar mass	409.530 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C2=CC(=C(C=C2N1)OC)OC)CCN3CCN(CC3)C4=CC=CC=C4OC;
	InChI InChI=1S/C24H31N3O3/c1-17-18(19-15-23(29-3)24(30-4)16-20(19)25-17)9-10-26-11-13-27(14-12-26)21-7-5-6-8-22(21)28-2/h5-8,15-16,25H,9-14H2,1-4H3; Key:XYAANYFFYIRFND-UHFFFAOYSA-N;

Milipertine (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name; developmental code name WIN-18935) is a drug of the pertine group described as an antipsychotic, neuroleptic, and tranquilizer which was under development for the treatment of schizophrenia but was never marketed.

Structurally, it is a substituted tryptamine and a piperazinylethylindole. The drug is closely structurally related to other "pertines" including alpertine, 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. ortho-Methoxyphenylpiperazine (oMeOPP) has been said to be a metabolite of milipertine, as well as of oxypertine and several other drugs.

Milipertine produced troublesome side effects in clinical studies including orthostatic hypotension, drowsiness, extrapyramidal symptoms, elevated liver enzymes, and weight loss. The side effects of milipertine occurred too frequently and at doses well below those producing antipsychotic effects and its development was abandoned.

Milipertine was first described in the scientific literature by 1968.