| Identification | Back Directory | [Name]
SA-4503,1-(3,4-DIMETHOXYPHENETHYL)-4-(3-PHENYLPROPYL)PIPERAZINE DIHYDROCHLORIDE | [CAS]
165377-44-6 | [Synonyms]
SA-4503
CS-2246
SA-4503(2HCl)
Cutamesine HCl
SA 4503;SA-4503
SA4503 >=98% (HPLC)
Cutamesine hydrochloride
AGY94806 dihydrochloride
SA 4503 (dihydrochloride)
Cutamesine dihydrochloride
Cutamesine HCl (SA-4503 HCl)
SA4503 DIHYDROCHLORIDE;AGY94806 DIHYDROCHLORIDE
1-(3,4-Dimethoxyphenethyl)-4-(3-phenylpropyl)piperazinedihydrochloride
1-[2-(3,4-Dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine hydrochloride
1-[2-(3,4-DiMethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride
SA-4503,1-(3,4-DIMETHOXYPHENETHYL)-4-(3-PHENYLPROPYL)PIPERAZINE DIHYDROCHLORIDE
SA4503; SA 4503; SA-4503; AGY94806; AGY-94806; AGY 94806; CUTAMESINE HCL; CUTAMESINE HYDROCHLORIDE | [Molecular Formula]
C23H32N2O2.2ClH | [MDL Number]
MFCD00939308 | [MOL File]
165377-44-6.mol | [Molecular Weight]
441.44 |
| Chemical Properties | Back Directory | [Melting point ]
250-252°C | [storage temp. ]
2-8°C | [solubility ]
Soluble in DMSO (up to 5 mg/ml) or in Water (up to at least 25 mg/ml).. | [form ]
powder | [color ]
white to beige | [Water Solubility ]
H2O: 2mg/mL, clear | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month. | [InChI]
1S/C23H32N2O2.2ClH/c1-26-22-11-10-21(19-23(22)27-2)12-14-25-17-15-24(16-18-25)13-6-9-20-7-4-3-5-8-20;;/h3-5,7-8,10-11,19H,6,9,12-18H2,1-2H3;2*1H | [InChIKey]
XWOXAKBQEMQMFH-UHFFFAOYSA-N | [SMILES]
COC1=CC=C(CCN2CCN(CCCC3=CC=CC=C3)CC2)C=C1OC |
| Hazard Information | Back Directory | [Description]
SA4503 (165377-44-6) is a potent and selective sigma 1 agonist (σ1 IC50?= 17.4 nM, σ2 IC50?= 1784 nM).1?It has been investigated as a cognition enhancer2,3, antidepressant4,5, anti-addiction agent6, and neuroprotectant7-10. | [Uses]
SA 4503 Dihydrochloride is a novel and selective σ1 receptor agonist. | [Biochem/physiol Actions]
SA4503 is a high affinity, orally active non-opioid intracellular receptor sigma-1 (σ1R) selective agonist (IC50 = 17.4 nM against 200 nM (+)-pentazocine for binding σ1R), exhibiting ~100-fold less affinity for the sigma 2 receptor subtype (σ2R) and little or no affinity toward 36 other receptors, ion channels and second messenger systems. Oral administration is reported to elicit cerebral acetylcholine (ACh) release in rat frontal cortex and hippocampus (5-20 mg/kg p.o.) and reduce immobility time in a mouse forced swimming test (Immobility time = 214.8 s without vs. 111.6 s with 1.0 mg/kg oral dosage). | [in vivo]
Cutamesine extends the survival time in the SOD1G93A mice[2]. | [IC 50]
Sigma 1 Receptor | [storage]
Desiccate at RT | [References]
1) Matsuno?et al.?(1996),?Binding properties of SA4503, a novel and selective sigma 1 receptor agonist; Eur. J. Pharmacol.?306?271
2) Matsuno?et al.?(1997),?SA4503, a novel cognition enhancer with sigma 1 agonistic properties; Behav. Brain Res.?83?221
3) Niitsu?et al.?(2012),?Sigma-1 receptor agonists as therapeutic drugs for cognitive impairment in neuropsychiatric diseases; Curr. Pharm. Des.?18?875
4) Skuza and Rogoz?et al.?(2002),?A potential antidepressant activity of SA4503, a selective sigma 1 receptor agonist; Behav. Pharmacol.?13 537
5) Lucas?et al.?(2008),?Further evidence for an antidepressant potential of the selective sigma1 agonist SA4503: electrophysiological, morphological and behavioral studies; Int. J. Neuropsychopharmacol.?11?485
6) Mori?et al.?(2014),?Inhibitory effects of SA4503 on the rewarding effects of abused drugs; Addict. Biol.?19?362
7) Nakazawa?et al. (1998),?Activation of sigma1 receptor subtype leads to neuroprotection in the rat primary neuronal cultures; Neurochem. Int.?32?337
8) Ruscher?et al.?(2011),?The sigma-1 receptor enhances brain plasticity and functional recovery after experimental stroke; Brain?134(Pt.3)?732
9) Ruscher?et al.?(2012),?Effects of the sigma-1 receptor agonist 1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine dihydrochloride on inflammation after stroke; PLoS One.?7?e45118
10) Yamashita?et al.?(2015),?Neuroprotective effects of cutamesine, a ligand of the sigma-1 receptor chaperone, against noise-induced hearing loss; Int. J. Neurosci. Res.?93?788 |
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