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165377-44-6,MFCD00939308
Catalog No.:AA001W1K

165377-44-6 | 1-(3,4-Dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine dihydrochloride

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10mg
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25mg
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250mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA001W1K
Chemical Name:
1-(3,4-Dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine dihydrochloride
CAS Number:
165377-44-6
Molecular Formula:
C23H34Cl2N2O2
Molecular Weight:
441.4343
MDL Number:
MFCD00939308
SMILES:
COc1cc(CCN2CCN(CC2)CCCc2ccccc2)ccc1OC.Cl.Cl
Properties
Computed Properties
 
Complexity:
392  
Covalently-Bonded Unit Count:
3  
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
9  

Downstream Synthesis Route

[1]CurrentPatentAssignee:M'SSCIENCECORPORATION-US5736546,1998,A

[1]CurrentPatentAssignee:M'SSCIENCECORPORATION-WO2007/21545,2007,A2Locationinpatent:Page/Pagecolumn17-18

Literature

Title: Application of [¹¹C]SA4503 to selection of novel σ₁ selective agonists.

Journal: Nuclear medicine and biology 20121101

Title: Re-evaluation of in vivo selectivity of [(11)C]SA4503 to σ(1) receptors in the brain: contributions of emopamil binding protein.

Journal: Nuclear medicine and biology 20121001

Title: Sigma-1 receptor chaperones regulate the secretion of brain-derived neurotrophic factor.

Journal: Synapse (New York, N.Y.) 20120701

Title: Attenuating heat-induced acute lung inflammation and injury by dextromethorphan in rats.

Journal: American journal of respiratory cell and molecular biology 20120301

Title: Effects of the sigma-1 receptor agonist 1-(3,4-dimethoxyphenethyl)-4-(3-phenylpropyl)-piperazine dihydro-chloride on inflammation after stroke.

Journal: PloS one 20120101

Title: Chloroquine inhibits glutamate-induced death of a neuronal cell line by reducing reactive oxygen species through sigma-1 receptor.

Journal: Journal of neurochemistry 20111101

Title: Synthesis and in vitro biological evaluation of carbonyl group-containing analogues for σ1 receptors.

Journal: Journal of medicinal chemistry 20110811

Title: The sigma receptor agonist SA4503 both attenuates and enhances the effects of methamphetamine.

Journal: Drug and alcohol dependence 20110701

Title: The sigma-1 receptor enhances brain plasticity and functional recovery after experimental stroke.

Journal: Brain : a journal of neurology 20110301

Title: SA 4503 attenuates cocaine-induced hyperactivity and enhances methamphetamine substitution for a cocaine discriminative stimulus.

Journal: Pharmacology, biochemistry, and behavior 20110201

Title: Potentiation of nerve growth factor-induced neurite outgrowth by the ROCK inhibitor Y-27632: a possible role of IP₃ receptors.

Journal: European journal of pharmacology 20101201

Title: 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.

Journal: Neuroscience letters 20100129

Title: High occupancy of sigma1 receptors in the human brain after single oral administration of donepezil: a positron emission tomography study using [11C]SA4503.

Journal: The international journal of neuropsychopharmacology 20090901

Title: Imaging of sigma1 receptors in the human brain using PET and [11C]SA4503.

Journal: Central nervous system agents in medicinal chemistry 20090901

Title: Steroid hormones affect binding of the sigma ligand 11C-SA4503 in tumour cells and tumour-bearing rats.

Journal: European journal of nuclear medicine and molecular imaging 20090701

Title: Further evidence for an antidepressant potential of the selective sigma1 agonist SA 4503: electrophysiological, morphological and behavioural studies.

Journal: The international journal of neuropsychopharmacology 20080601

Title: Shortened protocol in practical [11C]SA4503-PET studies for sigma1 receptor quantification.

Journal: Annals of nuclear medicine 20080201

Title: 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.

Journal: Nuclear medicine and biology 20080101

Title: Potentiation of nerve growth factor-induced neurite outgrowth by fluvoxamine: role of sigma-1 receptors, IP3 receptors and cellular signaling pathways.

Journal: PloS one 20080101

Title: Effects of selective sigma receptor ligands on glucocorticoid receptor-mediated gene transcription in LMCAT cells.

Journal: Pharmacological reports : PR 20080101

Title: High occupancy of sigma-1 receptors in the human brain after single oral administration of fluvoxamine: a positron emission tomography study using [11C]SA4503.

Journal: Biological psychiatry 20071015

Title: 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.

Journal: The Journal of pharmacology and experimental therapeutics 20070901

Title: Rapid reduction of sigma1-receptor binding and 18F-FDG uptake in rat gliomas after in vivo treatment with doxorubicin.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20070801

Title: In vivo characterization of radioiodinated (+)-2-[4-(4-iodophenyl) piperidino] cyclohexanol as a potential sigma-1 receptor imaging agent.

Journal: Nuclear medicine and biology 20070801

Title: American Chemical Society--233rd National Meeting. CNS, cancer and cardiovascular targets. 25-29 March 2007, Chicago, IL, USA.

Journal: IDrugs : the investigational drugs journal 20070501

Title: Phencyclidine-induced cognitive deficits in mice are improved by subsequent subchronic administration of fluvoxamine: role of sigma-1 receptors.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20070301

Title: Mapping of human cerebral sigma1 receptors using positron emission tomography and [11C]SA4503.

Journal: NeuroImage 20070301

Title: Antidepressant-like effect of combined treatment with selective sigma receptor agonists and a 5-HT1A receptor agonist in the forced swimming test in rats.

Journal: Pharmacological reports : PR 20070101

Title: 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.

Journal: Annals of nuclear medicine 20061001

Title: The synergistic effect of selective sigma receptor agonists and uncompetitive NMDA receptor antagonists in the forced swim test in rats.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20060601

Title: Sigma1 and sigma2 receptor binding affinity and selectivity of SA4503 and fluoroethyl SA4503.

Journal: Synapse (New York, N.Y.) 20060501

Title: Evaluation of (+)-p-[11C]methylvesamicol for mapping sigma1 receptors: a comparison with [11C]SA4503.

Journal: Nuclear medicine and biology 20060501

Title: Function of sigma1 receptors in Parkinson's disease.

Journal: Acta neurologica Scandinavica 20050801

Title: Tumor imaging with 2 sigma-receptor ligands, 18F-FE-SA5845 and 11C-SA4503: a feasibility study.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20041101

Title: Behavioral pharmacology of sigma-ligands.

Journal: Pharmacopsychiatry 20041101

Title: Improved synthesis of [11C]SA4503, [11C]MPDX and [11C]TMSX by use of [11C]methyl triflate.

Journal: Annals of nuclear medicine 20040401

Title: Different brain kinetics of two sigma 1 receptor ligands, [3H](+)-pentazocine and [11C]SA4503, by P-glycoprotein modulation.

Journal: Synapse (New York, N.Y.) 20030501

Title: Sigma1 and dopamine D2 receptor occupancy in the mouse brain after a single administration of haloperidol and two dopamine D2-like receptor ligands.

Journal: Nuclear medicine and biology 20030501

Title: Age-related changes of the binding of [3h]SA4503 to sigma1 receptors in the rat brain.

Journal: Annals of nuclear medicine 20030201

Title: Potential antidepressant activity of sigma ligands.

Journal: Polish journal of pharmacology 20030101

Title: A potential antidepressant activity of SA4503, a selective sigma 1 receptor agonist.

Journal: Behavioural pharmacology 20021101

Title: Effects of sigma(1) receptor ligand MS-377 on D(2) antagonists-induced behaviors.

Journal: Pharmacology, biochemistry, and behavior 20021001

Title: Effect of SA4503 on the electrically evoked release of (3)H-acetylcholine from striatal and hippocampal rat brain slices.

Journal: Synapse (New York, N.Y.) 20021001

Title: Synthesis and evaluation of [18F]fluoroethyl SA4503 as a PET ligand for the sigma receptor.

Journal: Synapse (New York, N.Y.) 20020315

Title: [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.

Journal: Nuclear medicine and biology 20011001

Title: 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.

Journal: European journal of pharmacology 20010824

Title: The anti-amnesic effects of sigma1 (sigma1) receptor agonists confirmed by in vivo antisense strategy in the mouse.

Journal: Brain research 20010413

Title: Phencyclidine impairs latent learning in mice: interaction between glutamatergic systems and sigma(1) receptors.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20010401

Title: Repeated treatment with SA4503, a selective sigma1 receptor agonist, up-regulates alpha-adrenergic system. a behavioral study.

Journal: Polish journal of pharmacology 20010101

Title: SA4503, a novel cognitive enhancer with sigma1 receptor agonist properties, facilitates NMDA receptor-dependent learning in mice.

Journal: European journal of pharmacology 19970605

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

Title: 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.

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Tags:165377-44-6 Molecular Formula|165377-44-6 MDL|165377-44-6 SMILES|165377-44-6 1-(3,4-Dimethoxyphenethyl)-4-(3-phenylpropyl)piperazine dihydrochloride