Solypertine

Solypertine (INNTooltip International Nonproprietary Name; developmental code name WIN-18413), also known as solypertine tartrate (USANTooltip United States Adopted Name) in the case of the tartrate salt, is a drug of the pertine group described as an antiadrenergic (or adrenolytic/sympatholytic) and as also potentially possessing neuroleptic properties which was never marketed.^{[1][2][3][4][5]}

Other namesSolipertine; WIN18413; WIN-18,413; Win-18413; WIN 18413-2

ATC code

• None

CAS Number

• 4448-96-8
  5591-43-5 (tartrate)

PubChem CID

• 20517

Quick facts Clinical data, Other names ...

Solypertine

Clinical data
Other names	Solipertine; WIN18413; WIN-18,413; Win-18413; WIN 18413-2
ATC code	None
Identifiers
IUPAC name 7-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-5H-[1,3]dioxolo[4,5-f]indole
CAS Number	4448-96-8 5591-43-5 (tartrate)
PubChem CID	20517
ChemSpider	19323
UNII	9BUF6DCO0C
ChEMBL	ChEMBL1739674
CompTox Dashboard (EPA)	DTXSID50196189
Chemical and physical data
Formula	C22H25N3O3
Molar mass	379.460 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC=CC=C1N2CCN(CC2)CCC3=CNC4=CC5=C(C=C43)OCO5
InChI InChI=1S/C22H25N3O3/c1-26-20-5-3-2-4-19(20)25-10-8-24(9-11-25)7-6-16-14-23-18-13-22-21(12-17(16)18)27-15-28-22/h2-5,12-14,23H,6-11,15H2,1H3 Key:GIWODWVYEOAGQV-UHFFFAOYSA-N

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Structurally, it is a substituted tryptamine and a piperazinylethylindole.^[6] The drug is closely structurally related to other "pertines" including alpertine, milipertine, and oxypertine, which are also tryptamines and piperazinylethylindoles.^[6] Solypertine can be synthesized from 5,6-methylenedioxyindole.^[7]

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.^[8][9] Oxypertine, milipertine, and solypertine all antagonize the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals.^[8][10] ortho-Methoxyphenylpiperazine (oMeOPP) has been said to be a metabolite of milipertine and oxypertine.^[11][12]

Solypertine was first described in the scientific literature by 1962.^[1][13]