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SML2181

Sigma-Aldrich

SA4503

≥98% (HPLC)

Synonym(s):

1-(3,4-Dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine dihydrochloride, AGY 94806, AGY94806, Cutamesine, SA 4503

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About This Item

Empirical Formula (Hill Notation):
C23H32N2O2 · 2HCl
CAS Number:
165377-44-6
Molecular Weight:
441.43
MDL number:
MFCD09842336
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

COC1=CC=C(CCN2CCN(CCCC3=CC=CC=C3)CC2)C=C1OC

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

InChI key

XWOXAKBQEMQMFH-UHFFFAOYSA-N

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).

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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K Matsuno et al.
European journal of pharmacology, 312(3), 267-271 (1996-10-03)
The immobility time in the mouse forced swimming test was dose-dependently reduced by sigma 1 receptor agonists, such as 1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine dihydrochloride (SA4503) and (+)-pentazocine, and non-specific sigma receptor agonists, such as 1,3-di(2-tolyl)guanidine (DTG) and (+)-N-cyclopropyl-methyl-N-methyl-1,4-diphenyl-1-yl-but-3-en-1-ylamin e hydrochloride (JO-1784). On the
Andrew J Rennekamp et al.
Nature chemical biology, 12(7), 552-558 (2016-05-31)
Humans and many animals show 'freezing' behavior in response to threatening stimuli. In humans, inappropriate threat responses are fundamental characteristics of several mental illnesses. To identify small molecules that modulate threat responses, we developed a high-throughput behavioral assay in zebrafish
Mori Tomohisa et al.
Synapse (New York, N.Y.), 69(11), 526-532 (2015-08-04)
Previous studies have shown that ligands of the sigma-1 receptor chaperone (Sig-1R) regulate pain-related behaviors. Clinical use of chemotherapeutics is often compromised due to their adverse side effects, particularly those related to neuropathy. Previous studies have shown that repeated administration
Yasuharu Shinoda et al.
PloS one, 11(10), e0163992-e0163992 (2016-10-16)
Cardiovascular diseases are risk factors for depression in humans. We recently proposed that σ1 receptor (σ1R) stimulation rescued cardiac hypertrophy and heart failure induced by transverse aortic constriction (TAC) in mice. Importantly, σ1R stimulation reportedly ameliorates depression-like behaviors in rodents.
Dennis K Miller et al.
Pharmacology, biochemistry, and behavior, 150-151, 198-206 (2016-11-17)
This study examined the effect of the N-phenylpropyl-N'-substituted piperazine ligands SA4503 (3.4-dimethoxyphenethyl), YZ-067 (4-methoxyphenethyl), YZ-185 (3-methoxyphenethyl) and Nahas-3h (4-methoxybenzyl) on methamphetamine-induced hyperactivity in mice. In a previous study in rats, SA4503 increased methamphetamine-induced hyperactivity at a lower ligand dose and
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