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Siramesine hydrochloride - 10mM in DMSO, high purity , CAS No.224177-60-0

    Grade & Purity:
  • 10mM in DMSO
In stock
Item Number
S422694
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S422694-1ml
1ml
Available within 4-8 weeks(?)
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$241.90

High affinity σ agonist (σ2> σ1)

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Compound libraries (12325)

Basic Description

Synonyms Siramesine hydrochloride | 224177-60-0 | Siramesine HCl | Siramesine (hydrochloride) | SiraMesine, Lu-28-179 | 39CG1EG1SS | Siramesine (lu-28-179) | 1'-(4-(1-(4-Fluorophenyl)-1H-indol-3-yl)butyl)-3H-spiro[isobenzofuran-1,4'-piperidine] hydrochloride | 1/'-[4-[1-(4-fluoro
Specifications & Purity 10mM in DMSO
Biochemical and Physiological Mechanisms High affinity σ receptor agonist (Kivalues are 0.19 and 17 nM for σ2and σ1receptors, respectively). Displays anxiolytic and antidepressant effects in rodents. Also induces cell death in tumor cell lines.
Storage Temp Store at -80°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Product Description

Siramesine (Lu 28-179) hydrochloride is a potent sigma-2 receptor agonist. Siramesine hydrochloride has a subnanomolar affinity for sigma-2 receptors (IC50=0.12 nM) and exhibits a 140-fold selectivity for sigma-2 receptors over sigma-1 receptors (IC50=17 nM). Siramesine hydrochloride triggers cell death through destabilisation of mitochondria, but not lysosomes. Anti-cancer activity.


Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Organoheterocyclic compounds
Class Pyrroles
Subclass Substituted pyrroles
Intermediate Tree Nodes Not available
Direct Parent Phenylpyrroles
Alternative Parents 3-alkylindoles  Isocoumarans  Isobenzofurans  Fluorobenzenes  Aralkylamines  Piperidines  Aryl fluorides  Heteroaromatic compounds  Trialkylamines  Oxacyclic compounds  Dialkyl ethers  Azacyclic compounds  Organofluorides  Hydrochlorides  Hydrocarbon derivatives  
Molecular Framework Aromatic heteropolycyclic compounds
Substituents 1-phenylpyrrole - 3-alkylindole - Indole - Indole or derivatives - Isocoumaran - Isobenzofuran - Fluorobenzene - Halobenzene - Aralkylamine - Aryl fluoride - Benzenoid - Piperidine - Aryl halide - Monocyclic benzene moiety - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Oxacycle - Azacycle - Dialkyl ether - Ether - Organic nitrogen compound - Amine - Hydrocarbon derivative - Hydrochloride - Organooxygen compound - Organic oxygen compound - Organohalogen compound - Organofluoride - Organonitrogen compound - Aromatic heteropolycyclic compound
Description This compound belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
External Descriptors Not available

Names and Identifiers

IUPAC Name 1'-[4-[1-(4-fluorophenyl)indol-3-yl]butyl]spiro[1H-2-benzofuran-3,4'-piperidine];hydrochloride
INCHI InChI=1S/C30H31FN2O.ClH/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;1H
InChIKey ILSRGIFRZZSGPN-UHFFFAOYSA-N
Smiles C1CN(CCC12C3=CC=CC=C3CO2)CCCCC4=CN(C5=CC=CC=C54)C6=CC=C(C=C6)F.Cl
Isomeric SMILES C1CN(CCC12C3=CC=CC=C3CO2)CCCCC4=CN(C5=CC=CC=C54)C6=CC=C(C=C6)F.Cl
PubChem CID 9891778
Molecular Weight 491.04

Certificates(CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

Sensitivity Heat Sensitive
Melt Point(°C) 225 °C
Molecular Weight 491.000 g/mol
XLogP3
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 3
Rotatable Bond Count 6
Exact Mass 490.219 Da
Monoisotopic Mass 490.219 Da
Topological Polar Surface Area 17.400 Ų
Heavy Atom Count 35
Formal Charge 0
Complexity 656.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 0
Covalently-Bonded Unit Count 2

Solution Calculators

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