Oxypertine

Oxypertine, sold under the brand name Oxypertine among others, is an antipsychotic medication of the tryptamine and phenylpiperazine groups which was previously used in the treatment of schizophrenia but is no longer marketed.^[2] It was also evaluated for the treatment of anxiety.^[3]

Oxypertine

Clinical data
Trade names	Oxypertine, others
Other names	WIN-18501; WIN18501; WIN-18,501, Win-18501; Win-18501-2
AHFS/Drugs.com	International Drug Names
Routes of administration	By mouth
ATC code	N05AE01 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances)[1] In general: ℞ (Prescription only)
Identifiers
IUPAC name 5,6-Dimethoxy-2-methyl-3-[2-(4-phenylpiperazin-1-yl)ethyl]-1H-indole
CAS Number	153-87-7 Y
PubChem CID	4640
ChemSpider	4479 Y
UNII	5JGL4G25R7
KEGG	D01219 Y
CompTox Dashboard (EPA)	DTXSID20165185
ECHA InfoCard	100.005.291
Chemical and physical data
Formula	C23H29N3O2
Molar mass	379.504 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=C(C2=CC(=C(C=C2N1)OC)OC)CCN3CCN(CC3)C4=CC=CC=C4
InChI InChI=1S/C23H29N3O2/c1-17-19(20-15-22(27-2)23(28-3)16-21(20)24-17)9-10-25-11-13-26(14-12-25)18-7-5-4-6-8-18/h4-8,15-16,24H,9-14H2,1-3H3 N Key:XCWPUUGSGHNIDZ-UHFFFAOYSA-N N
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Pharmacology

Pharmacodynamics

The drug shows high affinity for the serotonin 5-HT₂ and dopamine D₂ receptors (K_i = 8.6 nM and 30 nM, respectively).^[4] It antagonizes the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals.^[4][5] Like reserpine and tetrabenazine, oxypertine depletes catecholamines, though not serotonin, possibly contributing to its antipsychotic effectiveness.^[6]

Chemistry

Chemically, it is a substituted tryptamine and phenylpiperazine derivative.^[7] Its chemical structure is similar to other "pertines" including alpertine, milipertine, and solypertine.^[8][9]

History

Oxypertine was first described in the scientific literature by 1962.^[10]

Society and culture

Names

Oxypertine is the generic name of the drug and its INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name, DCFTooltip Dénomination Commune Française, and JANTooltip Japanese Accepted Name.^{[10][11][12][13]} It is also known by its former developmental code name WIN-18501.^{[10][11][12][13]} The drug has been sold under brand names including Equipertine, Forit, Integrin, Lanturil, Lotawin, Opertil, and Oxypertine.^{[10][11][12][13]}