Delequamine

Delequamine (INNTooltip International Nonproprietary Name; developmental code names RS-15385, RS-15385-197) is a potent and selective α₂-adrenergic receptor antagonist which was under development for the treatment of erectile dysfunction and major depressive disorder but was never marketed.^[1][2][3][4]

Delequamine

Clinical data
Other names	DMMIN; RS-15385; RS 15385; RS15385; RS 15385-197; RS-15385-197; RS15385-197
Drug class	α2-Adrenergic receptor antagonist
Identifiers
IUPAC name (8aR,12aS,13aS)-3-methoxy-12-methylsulfonyl-5,6,8,8a,9,10,11,12a,13,13a-decahydroisoquinolino[2,1-g][1,6]naphthyridine
CAS Number	119813-87-5 119905-05-4
PubChem CID	60713
ChemSpider	54718
UNII	L37HF85G8S
ChEMBL	ChEMBL163911
CompTox Dashboard (EPA)	DTXSID301350815
Chemical and physical data
Formula	C18H26N2O3S
Molar mass	350.48 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC2=C(C=C1)[C@@H]3C[C@H]4[C@H](CCCN4S(=O)(=O)C)CN3CC2
InChI InChI=1S/C18H26N2O3S/c1-23-15-5-6-16-13(10-15)7-9-19-12-14-4-3-8-20(24(2,21)22)17(14)11-18(16)19/h5-6,10,14,17-18H,3-4,7-9,11-12H2,1-2H3/t14-,17+,18+/m1/s1 Key:JKDBLHWERQWYKF-JLSDUUJJSA-N

It is structurally related to the naturally occurring α₂-adrenergic receptor antagonist yohimbine but has greater selectivity in comparison.^[3][4] The drug has been found to affect sexual function and sleep in humans.^[4]

Delequamine reached phase 3 clinical trials prior to the discontinuation of its development.^[1] The drug was under development in the 1990s and its development was discontinued by 1999.^[1] It was first described in the scientific literature by 1990.^[5]