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165377-44-6

165377-44-6 structure
165377-44-6 structure
  • Name: SA 4503 dihydrochloride
  • Chemical Name: 1-(3,4-Dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine dihydrochloride
  • CAS Number: 165377-44-6
  • Molecular Formula: C23H34Cl2N2O2
  • Molecular Weight: 441.434
  • Catalog: Signaling Pathways GPCR/G Protein Sigma Receptor
  • Create Date: 2016-10-22 18:42:36
  • Modify Date: 2024-01-05 17:24:01
  • Cutamesine dihydrochloride (SA4503 dihydrochloride) is a potent Sigma 1 receptor agonist with an IC50 of 17.4 nM in guinea pig brain membranes.

Name 1-(3,4-Dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine dihydrochloride
Synonyms 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine,dihydrochloride
1-(3,4-Dimethoxyphenethyl)-4-(3-phenylpropyl)piperazinedihydrochloride
Piperazine, 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)-, hydrochloride (1:2)
1-[2-(3,4-Dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride
SA-4503
SA4503 2HCl
SA4503 (dihydrochloride)
Description Cutamesine dihydrochloride (SA4503 dihydrochloride) is a potent Sigma 1 receptor agonist with an IC50 of 17.4 nM in guinea pig brain membranes.
Related Catalog
Target

IC50: 17.4 nM (σ1receptor, guinea pig brain membranes)[1]

In Vitro The sigma receptor might be involved in several diseases in the central nervous system. Cutamesine, a potent σ1receptor agonist, has 103-fold higher affinity for σ1 (IC50=17.4 nM) than σ2 (IC50=1,784 nM) sites in guinea pig brain membranes. Cutamesine is 14-fold selective for σ1 (Ki=4.6 nM) over σ2 (Ki=63.1 nM) sites in guinea pig brain homogenates[1]. Cutamesine protects motor neuron NSC34 cells against superoxide dismutase 1 and serum free neurotoxicity. It upregulates the phosphorylation levels of Akt and extracellular signal-regulated kinase (ERK) 1/2[2]. Cutamesine reduces the activation of the MAPK/ERK pathway and down-regulated the ionotropic glutamate receptor, GluR1[3].
In Vivo Cutamesine extends the survival time in the SOD1G93A mice[2].
Cell Assay The NSC34 cells are seeded at a density of 7000 cells per well into 96-well plates with D-MEM and transfected using Lipofectamine 2000 mixed with 2 μg /mL of plasmid vector in D-MEM for 6 h. After 6 h, the cell-culture medium is replaced with fresh D-MEM and culture and allowed to proceed for a further 42 h. The cells are then transferred to serum-free D-MEM and immediately treated with Cutamesine at a final concentration of 1, 3, or 10 nM[2].
Animal Admin Mice: Transgenic female mice overexpressing mutated human SOD1G93A are used in the study. Cutamesine is dissolved in saline and subcutaneously administered at a dose of 1 mg/kg once daily to 5-week-old SOD1G93A mice to the time of death. In a control group, vehicle (saline) is subcutaneously administered at 10 ml/kg[2].
References

[1]. Lever JR, et al. Sigma1 and sigma2 receptor binding affinity and selectivity of SA4503 and fluoroethyl SA4503. Synapse. 2006 May;59(6):350-8.

[2]. Tuerxun T, et al. SA4503, a sigma-1 receptor agonist, prevents cultured cortical neurons from oxidative stress-induced cell death via suppression of MAPK pathway activation and glutamate receptor expression. Neurosci Lett. 2010 Jan 29;469(3):303-8.

Boiling Point 499.2ºC at 760 mmHg
Molecular Formula C23H34Cl2N2O2
Molecular Weight 441.434
Flash Point 137.3ºC
Exact Mass 440.199738
PSA 24.94000
LogP 4.97650
Vapour Pressure 4.25E-10mmHg at 25°C
HS Code 2933599090
HS Code 2933599090
Summary 2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%