Siramesine

Siramesine
Clinical data
ATC code	none;
Identifiers
	IUPAC name 1'-{4-[1-(4-Fluorophenyl)-1H-indol-3-yl]butyl}-3H-spiro[2-benzofuran-1,4'-piperidine];
CAS Number	147817-50-3 ;
PubChem CID	9829526;
ChemSpider	8005261 ;
UNII	3IX8CWR24V;
CompTox Dashboard (EPA)	DTXSID90163810 ;
Chemical and physical data
Formula	C30H31FN2O
Molar mass	454.589 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCC12C3=CC=CC=C3CO2)CCCCC4=CN(C5=CC=CC=C54)C6=CC=C(C=C6)F;
	InChI InChI=1S/C30H31FN2O/c31-25-12-14-26(15-13-25)33-21-23(27-9-2-4-11-29(27)33)7-5-6-18-32-19-16-30(17-20-32)28-10-3-1-8-24(28)22-34-30/h1-4,8-15,21H,5-7,16-20,22H2 ; Key:XWAONOGAGZNUSF-UHFFFAOYSA-N ;
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Siramesine (or Lu 28-179) is a sigma receptor agonist, selective for the σ2 subtype. In animal studies, siramesine has been shown to produce anxiolytic and antidepressant effects. It was developed by the pharmaceutical company H Lundbeck for the treatment of anxiety, although development was discontinued after clinical trials showed a lack of efficacy in humans. Siramesine has been shown to produce an enhanced antidepressant effect when co-administered with NMDA antagonists. It has also been used to study the σ2 activity of cocaine, and has been shown to produce anticancer properties both in vitro and in vivo.

Clinical data


ATC code	none
Identifiers
IUPAC name 1'-{4-[1-(4-Fluorophenyl)-1H-indol-3-yl]butyl}-3H-spiro[2-benzofuran-1,4'-piperidine]
CAS Number	147817-50-3^Y
PubChem CID	9829526
ChemSpider	8005261^N
UNII	3IX8CWR24V
CompTox Dashboard (EPA)	DTXSID90163810
Chemical and physical data
Formula	C₃₀H₃₁FN₂O
Molar mass	454.589 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CN(CCC12C3=CC=CC=C3CO2)CCCCC4=CN(C5=CC=CC=C54)C6=CC=C(C=C6)F
InChI InChI=1S/C30H31FN2O/c31-25-12-14-26(15-13-25)33-21-23(27-9-2-4-11-29(27)33)7-5-6-18-32-19-16-30(17-20-32)28-10-3-1-8-24(28)22-34-30/h1-4,8-15,21H,5-7,16-20,22H2^N Key:XWAONOGAGZNUSF-UHFFFAOYSA-N^N
^NY (what is this?) (verify)