Siramesine hydrochloride - ≥98% , CAS No.224177-60-0

CAS: 224177-60-0 Cat. No.: S288444 Molecular Weight: 491.04 PubChem CID: 9891778

GRADE & PURITY ≥98%

Synonyms

Lu 28-179;Lu-28-179;Lu 28-179 hydrochloride | 1'-(4-(1-(4-Fluorophenyl)-1H-indol-3-yl)butyl)-3H-spiro[isobenzofuran-1,4'-piperidine]hydrochloride | UNII-39CG1EG1SS | I1090 | Lu 28-179 hydrochloride | AKOS026750245 | FS-2246 | Siramesine-hydrochloride | 1/

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

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.

Specifications

Synonyms

Lu 28-179;Lu-28-179;Lu 28-179 hydrochloride | 1'-(4-(1-(4-Fluorophenyl)-1H-indol-3-yl)butyl)-3H-spiro[isobenzofuran-1, 4'-piperidine]hydrochloride | UNII-39CG1EG1SS | I1090 | Lu 28-179 hydrochloride | AKOS026750245 | FS-2246 | Siramesine-hydrochloride | 1/

Specifications & Purity

≥98%

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

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488196403
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488196403
• Canonical Smiles: C1CN(CCC12C3=CC=CC=C3CO2)CCCCC4=CN(C5=CC=CC=C54)C6=CC=C(C=C6)F.Cl
• IUPAC Name: 1'-[4-[1-(4-fluorophenyl)indol-3-yl]butyl]spiro[1H-2-benzofuran-3,4'-piperidine];hydrochloride
• InChIKey: ILSRGIFRZZSGPN-UHFFFAOYSA-N
• 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
• 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

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrroles
      • Subclass Substituted pyrroles

• 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

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 24.55, Max Conc. mM: 50
• Sensitivity: Heat Sensitive;Moisture sensitive
• Melt Point(°C): 225 °C
• Molecular Weight: 491.000 g/mol
• 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

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