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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).

Storage Class Code

11 - Combustible Solids

WGK

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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T Kobayashi et al.
The Journal of pharmacology and experimental therapeutics, 279(1), 106-113 (1996-10-01)
We found that 1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl) piperazine dihydrochloride (SA4503), a potent and selective sigma 1 receptor agonist, significantly enhanced the cerebral acetylcholine (ACh) release in the rat using in vivo brain microdialysis technique. Interestingly, the significant enhancement of ACh release elicited by
Rong Xu et al.
Bioorganic & medicinal chemistry, 23(1), 222-230 (2014-12-04)
Two series of novel ether analogs of the sigma (σ) receptor ligand 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine (SA4503) have been prepared. In one series, the alkyl portion of the 4-methoxy group was replaced with allyl, propyl, bromoethyl, benzyl, phenethyl, and phenylpropyl moieties. In the
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
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
K Matsuno et al.
European journal of pharmacology, 306(1-3), 271-279 (1996-06-13)
The binding profiles of SA4503 (1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine dihydrochloride), a novel sigma receptor ligand, to sigma 1 and sigma 2 receptor subtypes in guinea pig and rat brain membranes were evaluated. SA4503 showed a high affinity for the sigma 1 receptor subtype
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