Panamesine - ≥99% , CAS No.139225-22-2

CAS: 139225-22-2 Cat. No.: P649071 Formula: C₂₃H₂₆N₂O₆ Molecular Weight: 426.46 PubChem CID: 3047810

GRADE & PURITY ≥99%

Synonyms

2-Oxazolidinone, 5-[[4-(1,3-benzodioxol-5-yl)-4-hydroxy-1-piperidinyl]methyl]-3-(4-methoxyphenyl)-, (5S)- | Panamesine | Panamesine [INN] | Q27231486 | (5S)-5-[[4-(1,3-benzodioxol-5-yl)-4-hydroxypiperidin-1-yl]methyl]-3-(4-methoxyphenyl)-1,3-oxazolidin-2-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Panamesine (EMD 57445) is a sigma receptor ligand, which has a high affinity ( IC 50 6 nM) and selectivity for sigma binding sites. Panamesine is a potential atypical neuroleptic agent

In Vivo

Panamesine (EMD 57445; 0.3, 1, 3, 30 mg/kg) induces a dose-dependent increase of c-fos expression in several cortical areas with the strongest signals in the piriform cortex . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Female Sprague Dawley rats aged 2 months with a body weights of 200-250 g Dosage: 0.3, 1, 3, 30 mg/kg Administration: Subcutanous injections Result: Specific c-fos gene expression was detected at all concentrations (0.3 mg/kg, 1 mg/kg, 3 mg/kg, 30 mg/kg) tested in frontal, parietal, perirhinal, temporal, piriform, insular, limbic, cingulate and occipital cortex.

Form:Solid

IC50& Target:IC50: 6 nM (sigma receptor)

Specifications

Synonyms

2-Oxazolidinone, 5-[[4-(1,3-benzodioxol-5-yl)-4-hydroxy-1-piperidinyl]methyl]-3-(4-methoxyphenyl)-, (5S)- | Panamesine | Panamesine [INN] | Q27231486 | (5S)-5-[[4-(1,3-benzodioxol-5-yl)-4-hydroxypiperidin-1-yl]methyl]-3-(4-methoxyphenyl)-1,3-oxazolidin-2-

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Panamesine (EMD 57445) is a sigma receptor ligand, which has a high affinity ( IC 50 6 nM) and selectivity for sigma binding sites. Panamesine is a potential atypical neuroleptic agent.

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

≥99%

Names and Identifiers

• Canonical Smiles: COC1=CC=C(C=C1)N2CC(OC2=O)CN3CCC(CC3)(C4=CC5=C(C=C4)OCO5)O
• IUPAC Name: (5S)-5-[[4-(1,3-benzodioxol-5-yl)-4-hydroxypiperidin-1-yl]methyl]-3-(4-methoxyphenyl)-1,3-oxazolidin-2-one
• InChIKey: NINYZUDVKTUKIA-IBGZPJMESA-N
• INCHI: 1S/C23H26N2O6/c1-28-18-5-3-17(4-6-18)25-14-19(31-22(25)26)13-24-10-8-23(27,9-11-24)16-2-7-20-21(12-16)30-15-29-20/h2-7,12,19,27H,8-11,13-15H2,1H3/t19-/m0/s1
• Isomeric SMILES: COC1=CC=C(C=C1)N2C[C@@H](OC2=O)CN3CCC(CC3)(C4=CC5=C(C=C4)OCO5)O
• Alternate CAS: 139225-22-2
• PubChem CID: 3047810
• MeSH Entry Terms: (5S)-5-((4-Hydroxy-4-(3,4-(methylenedioxy)phenyl)piperidino)methyl)-3-(p-methoxyphenyl)-2-oxazolidinone;5-(4-hydroxy-4-(1,3-benzodioxol-5-yl)piperidine-1-ylmethyl)-3-(4-methoxyphenyl)oxazolidine-2-one hydrochloride;EMD 57445;EMD-57445;panamesine
• Molecular Weight: 426.46

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Piperidines
      • Subclass Phenylpiperidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Piperidines
• Subclass: Phenylpiperidines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpiperidines
• Alternative Parents: Methoxyanilines Benzodioxoles Phenoxy compounds Anisoles Methoxybenzenes Alkyl aryl ethers Aralkylamines Oxazolidinones Tertiary alcohols Carbamate esters Trialkylamines Acetals Oxacyclic compounds Azacyclic compounds Organic oxides Organopnictogen compounds Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenylpiperidine - Methoxyaniline - Benzodioxole - Phenoxy compound - Methoxybenzene - Phenol ether - Anisole - Alkyl aryl ether - Aralkylamine - Benzenoid - Oxazolidinone - Monocyclic benzene moiety - Tertiary alcohol - Carbamic acid ester - Oxazolidine - Tertiary amine - Tertiary aliphatic amine - Acetal - Ether - Oxacycle - Azacycle - Organonitrogen compound - Alcohol - Carbonyl group - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
• 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

Associated Targets(Human)

SIGMAR1 Tclin Sigma non-opioid intracellular receptor 1 (1 Activities)

Discover Target: SIGMAR1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 125 mg/mL (293.11 mM; Need ultrasonic)
• Molecular Weight: 426.500 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 426.179 Da
• Monoisotopic Mass: 426.179 Da
• Topological Polar Surface Area: 80.700 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 632.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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: 1

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 139225-22-2, the molecular formula is C23H26N2O6, and the molecular weight is 426.46 g/mol. InChIKey NINYZUDVKTUKIA-IBGZPJMESA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.