Home Other Building Blocks Piperazine, 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)-

Piperazine, 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)-

CAS No.:
165377-43-5
Catalog Number:
AG001W4D
Molecular Formula:
C23H32N2O2
Molecular Weight:
368.5124
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Product Description
Catalog Number:
AG001W4D
Chemical Name:
Piperazine, 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)-
CAS Number:
165377-43-5
Molecular Formula:
C23H32N2O2
Molecular Weight:
368.5124
MDL Number:
MFCD09842336
IUPAC Name:
1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine
InChI:
InChI=1S/C23H32N2O2/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
InChI Key:
UVSWWUWQVAQPJR-UHFFFAOYSA-N
SMILES:
COc1cc(CCN2CCN(CC2)CCCc2ccccc2)ccc1OC
UNII:
9J7A4144BX
Properties
Complexity:
392  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
368.246g/mol
Formal Charge:
0
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
368.521g/mol
Monoisotopic Mass:
368.246g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
24.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.9  
Literature
Title Journal
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Re-evaluation of in vivo selectivity of [(11)C]SA4503 to σ(1) receptors in the brain: contributions of emopamil binding protein. Nuclear medicine and biology 20121001
Exploration of ring size in a series of cyclic vicinal diamines with σ₁ receptor affinity. Bioorganic & medicinal chemistry letters 20120901
Sigma-1 receptor chaperones regulate the secretion of brain-derived neurotrophic factor. Synapse (New York, N.Y.) 20120701
Attenuating heat-induced acute lung inflammation and injury by dextromethorphan in rats. American journal of respiratory cell and molecular biology 20120301
Effects of the sigma-1 receptor agonist 1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)-piperazine dihydro-chloride on inflammation after stroke. PloS one 20120101
Chloroquine inhibits glutamate-induced death of a neuronal cell line by reducing reactive oxygen species through sigma-1 receptor. Journal of neurochemistry 20111101
The sigma receptor agonist SA4503 both attenuates and enhances the effects of methamphetamine. Drug and alcohol dependence 20110701
Effect of structural modification in the amine portion of substituted aminobutyl-benzamides as ligands for binding σ1 and σ2 receptors. Bioorganic & medicinal chemistry 20110315
The sigma-1 receptor enhances brain plasticity and functional recovery after experimental stroke. Brain : a journal of neurology 20110301
SA 4503 attenuates cocaine-induced hyperactivity and enhances methamphetamine substitution for a cocaine discriminative stimulus. Pharmacology, biochemistry, and behavior 20110201
Potentiation of nerve growth factor-induced neurite outgrowth by the ROCK inhibitor Y-27632: a possible role of IP₃ receptors. European journal of pharmacology 20101201
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. Neuroscience letters 20100129
Sigma-1 receptor agonist fluvoxamine for delirium in patients with Alzheimer's disease. Annals of general psychiatry 20100101
Fluvoxamine for aripiprazole-associated akathisia in patients with schizophrenia: a potential role of sigma-1 receptors. Annals of general psychiatry 20100101
Fluvoxamine for blonanserin-associated akathisia in patients with schizophrenia: report of five cases. Annals of general psychiatry 20100101
Sigma-1 receptor agonist fluvoxamine for delirium in intensive care units: report of five cases. Annals of general psychiatry 20100101
Sigma-1 receptor agonist fluvoxamine for postoperative delirium in older adults: report of three cases. Annals of general psychiatry 20100101
High occupancy of sigma1 receptors in the human brain after single oral administration of donepezil: a positron emission tomography study using [11C]SA4503. The international journal of neuropsychopharmacology 20090901
Imaging of sigma1 receptors in the human brain using PET and [11C]SA4503. Central nervous system agents in medicinal chemistry 20090901
Steroid hormones affect binding of the sigma ligand 11C-SA4503 in tumour cells and tumour-bearing rats. European journal of nuclear medicine and molecular imaging 20090701
Pharmacology and therapeutic potential of sigma(1) receptor ligands. Current neuropharmacology 20081201
Further evidence for an antidepressant potential of the selective sigma1 agonist SA 4503: electrophysiological, morphological and behavioural studies. The international journal of neuropsychopharmacology 20080601
Shortened protocol in practical [11C]SA4503-PET studies for sigma1 receptor quantification. Annals of nuclear medicine 20080201
Synthesis and structure-activity relationships of N-(3-phenylpropyl)-N'-benzylpiperazines: Potent ligands for sigma1 and sigma2 receptors. Bioorganic & medicinal chemistry 20080115
A change of in vivo characteristics depending on specific activity of radioiodinated (+)-2-[4-(4-iodophenyl)piperidino]cyclohexanol [(+)-pIV] as a ligand for sigma receptor imaging. Nuclear medicine and biology 20080101
Potentiation of nerve growth factor-induced neurite outgrowth by fluvoxamine: role of sigma-1 receptors, IP3 receptors and cellular signaling pathways. PloS one 20080101
Effects of selective sigma receptor ligands on glucocorticoid receptor-mediated gene transcription in LMCAT cells. Pharmacological reports : PR 20080101
High occupancy of sigma-1 receptors in the human brain after single oral administration of fluvoxamine: a positron emission tomography study using [11C]SA4503. Biological psychiatry 20071015
Role of N-methyl-D-aspartate receptors in antidepressant-like effects of sigma 1 receptor agonist 1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine dihydrochloride (SA-4503) in olfactory bulbectomized rats. The Journal of pharmacology and experimental therapeutics 20070901
Rapid reduction of sigma1-receptor binding and 18F-FDG uptake in rat gliomas after in vivo treatment with doxorubicin. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20070801
In vivo characterization of radioiodinated (+)-2-[4-(4-iodophenyl) piperidino] cyclohexanol as a potential sigma-1 receptor imaging agent. Nuclear medicine and biology 20070801
American Chemical Society--233rd National Meeting. CNS, cancer and cardiovascular targets. 25-29 March 2007, Chicago, IL, USA. IDrugs : the investigational drugs journal 20070501
Phencyclidine-induced cognitive deficits in mice are improved by subsequent subchronic administration of fluvoxamine: role of sigma-1 receptors. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20070301
Mapping of human cerebral sigma1 receptors using positron emission tomography and [11C]SA4503. NeuroImage 20070301
Antidepressant-like effect of combined treatment with selective sigma receptor agonists and a 5-HT1A receptor agonist in the forced swimming test in rats. Pharmacological reports : PR 20070101
In vivo evaluation of radioiodinated 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)-piperazine derivatives as new ligands for sigma receptor imaging using single photon emission computed tomography. Biological & pharmaceutical bulletin 20061001
A feasibility study of [11C]SA4503-PET for evaluating sigmal receptor occupancy by neuroleptics: the binding of haloperidol to sigma1 and dopamine D2-like receptors. Annals of nuclear medicine 20061001
The synergistic effect of selective sigma receptor agonists and uncompetitive NMDA receptor antagonists in the forced swim test in rats. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20060601
Sigma1 and sigma2 receptor binding affinity and selectivity of SA4503 and fluoroethyl SA4503. Synapse (New York, N.Y.) 20060501
Evaluation of (+)-p-[11C]methylvesamicol for mapping sigma1 receptors: a comparison with [11C]SA4503. Nuclear medicine and biology 20060501
Synthesis and in vitro evaluation of iodinated derivatives of piperazine as a new ligand for sigma receptor imaging by single photon emission computed tomography. Chemical & pharmaceutical bulletin 20060401
Function of sigma1 receptors in Parkinson's disease. Acta neurologica Scandinavica 20050801
Tumor imaging with 2 sigma-receptor ligands, 18F-FE-SA5845 and 11C-SA4503: a feasibility study. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20041101
Behavioral pharmacology of sigma-ligands. Pharmacopsychiatry 20041101
Improved synthesis of [11C]SA4503, [11C]MPDX and [11C]TMSX by use of [11C]methyl triflate. Annals of nuclear medicine 20040401
Different brain kinetics of two sigma 1 receptor ligands, [3H](+)-pentazocine and [11C]SA4503, by P-glycoprotein modulation. Synapse (New York, N.Y.) 20030501
Sigma1 and dopamine D2 receptor occupancy in the mouse brain after a single administration of haloperidol and two dopamine D2-like receptor ligands. Nuclear medicine and biology 20030501
Age-related changes of the binding of [3h]SA4503 to sigma1 receptors in the rat brain. Annals of nuclear medicine 20030201
Potential antidepressant activity of sigma ligands. Polish journal of pharmacology 20030101
A potential antidepressant activity of SA4503, a selective sigma 1 receptor agonist. Behavioural pharmacology 20021101
Involvement of kappa-opioid and sigma receptors in short-term memory in mice. European journal of pharmacology 20021018
Effects of sigma(1) receptor ligand MS-377 on D(2) antagonists-induced behaviors. Pharmacology, biochemistry, and behavior 20021001
Effect of SA4503 on the electrically evoked release of (3)H-acetylcholine from striatal and hippocampal rat brain slices. Synapse (New York, N.Y.) 20021001
Synthesis and evaluation of [18F]fluoroethyl SA4503 as a PET ligand for the sigma receptor. Synapse (New York, N.Y.) 20020315
[11C]Raclopride binding was reduced in vivo by sigma(1) receptor ligand SA4503 in the mouse brain, while [11C]SA4503 binding was not by raclopride. Nuclear medicine and biology 20011001
The selective sigma(1) receptor agonist, 1-(3,4-dimethoxyphenethyl)-4-(phenylpropyl)piperazine (SA4503), blocks the acquisition of the conditioned place preference response to (-)-nicotine in rats. European journal of pharmacology 20010824
The anti-amnesic effects of sigma1 (sigma1) receptor agonists confirmed by in vivo antisense strategy in the mouse. Brain research 20010413
Phencyclidine impairs latent learning in mice: interaction between glutamatergic systems and sigma(1) receptors. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20010401
Repeated treatment with SA4503, a selective sigma1 receptor agonist, up-regulates alpha-adrenergic system. a behavioral study. Polish journal of pharmacology 20010101
Effect of sigma ligands on the cocaine-induced convulsions in mice. Polish journal of pharmacology 19990101
SA4503, a novel cognitive enhancer with sigma1 receptor agonist properties, facilitates NMDA receptor-dependent learning in mice. European journal of pharmacology 19970605
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