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138356-20-4 | 1,2-Ethanediamine, N1-[2-(3,4-dichlorophenyl)ethyl]-N1,N2,N2-trimethyl-
CAS No: 138356-20-4 Catalog No: AG0018MI MDL No:
Product Description
Catalog Number:
AG0018MI
Chemical Name:
1,2-Ethanediamine, N1-[2-(3,4-dichlorophenyl)ethyl]-N1,N2,N2-trimethyl-
CAS Number:
138356-20-4
Molecular Formula:
C13H20Cl2N2
Molecular Weight:
275.2173
IUPAC Name:
N'-[2-(3,4-dichlorophenyl)ethyl]-N,N,N'-trimethylethane-1,2-diamine
InChI:
InChI=1S/C13H20Cl2N2/c1-16(2)8-9-17(3)7-6-11-4-5-12(14)13(15)10-11/h4-5,10H,6-9H2,1-3H3
InChI Key:
MGVRNMUKTZOQOW-UHFFFAOYSA-N
SMILES:
CN(CCc1ccc(c(c1)Cl)Cl)CCN(C)C
UNII:
1S3X75QGDO
Properties
Complexity:
212
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
274.1g/mol
Formal Charge:
0
Heavy Atom Count:
17
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
275.217g/mol
Monoisotopic Mass:
274.1g/mol
Rotatable Bond Count:
6
Topological Polar Surface Area:
6.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.5
Literature
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|---|---|
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| Chloroquine inhibits glutamate-induced death of a neuronal cell line by reducing reactive oxygen species through sigma-1 receptor. | Journal of neurochemistry 20111101 |
| Fluvoxamine enhances prefrontal dopaminergic neurotransmission in adrenalectomized/castrated mice via both 5-HT reuptake inhibition and σ(1) receptor activation. | Psychopharmacology 20111001 |
| Afobazole modulates microglial function via activation of both sigma-1 and sigma-2 receptors. | The Journal of pharmacology and experimental therapeutics 20111001 |
| Afobazole modulates neuronal response to ischemia and acidosis via activation of sigma-1 receptors. | The Journal of pharmacology and experimental therapeutics 20111001 |
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| Tic hydantoin sigma-1 agonist: pharmacological characterization on cocaine-induced stimulant and appetitive effects. | European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20090701 |
| Sigma-1 receptors are essential for capsaicin-induced mechanical hypersensitivity: studies with selective sigma-1 ligands and sigma-1 knockout mice. | Pain 20090601 |
| Intrathecal injection of the neurosteroid, DHEAS, produces mechanical allodynia in mice: involvement of spinal sigma-1 and GABA receptors. | British journal of pharmacology 20090601 |
| Antiamnesic and neuroprotective effects of the aminotetrahydrofuran derivative ANAVEX1-41 against amyloid beta(25-35)-induced toxicity in mice. | Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20090501 |
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| Antidepressant-like effect of PRE-084, a selective sigma1 receptor agonist, in Albino Swiss and C57BL/6J mice. | Pharmacological reports : PR 20090101 |
| Intrathecal administration of sigma-1 receptor agonists facilitates nociception: involvement of a protein kinase C-dependent pathway. | Journal of neuroscience research 20081201 |
| Sigma-1 receptor regulation of voltage-gated calcium channels involves a direct interaction. | Investigative ophthalmology & visual science 20081101 |
| Intrathecal injection of the sigma(1) receptor antagonist BD1047 blocks both mechanical allodynia and increases in spinal NR1 expression during the induction phase of rodent neuropathic pain. | Anesthesiology 20081101 |
| Involvement of sigma (sigma1) receptors in modulating the anti-depressant effect of neurosteroids (dehydroepiandrosterone or pregnenolone) in mouse tail-suspension test. | Journal of psychopharmacology (Oxford, England) 20080801 |
| Possible involvement of sigma-1 receptors in the anti-immobility action of bupropion, a dopamine reuptake inhibitor. | Fundamental & clinical pharmacology 20080801 |
| Activation of the spinal sigma-1 receptor enhances NMDA-induced pain via PKC- and PKA-dependent phosphorylation of the NR1 subunit in mice. | British journal of pharmacology 20080701 |
| Anti-inflammatory effects of dimemorfan on inflammatory cells and LPS-induced endotoxin shock in mice. | British journal of pharmacology 20080701 |
| sigma-1 receptors protect RGC-5 cells from apoptosis by regulating intracellular calcium, Bax levels, and caspase-3 activation. | Investigative ophthalmology & visual science 20080601 |
| A new sigma ligand, (+/-)-PPCC, antagonizes kappa opioid receptor-mediated antinociceptive effect. | Life sciences 20080312 |
| Dimemorfan protects rats against ischemic stroke through activation of sigma-1 receptor-mediated mechanisms by decreasing glutamate accumulation. | Journal of neurochemistry 20080101 |
| Effects of selective sigma receptor ligands on glucocorticoid receptor-mediated gene transcription in LMCAT cells. | Pharmacological reports : PR 20080101 |
| Sigma 1 receptor-mediated increase in hippocampal extracellular dopamine contributes to the mechanism of the anticonvulsant action of neuropeptide Y. | The European journal of neuroscience 20071201 |
| Novel sigma (sigma) receptor agonists produce antidepressant-like effects in mice. | European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20071101 |
| Protective effects of the sigma agonist Pre-084 in the rat retina. | The British journal of ophthalmology 20071001 |
| Stereoselective action of (+)-morphine over (-)-morphine in attenuating the (-)-morphine-produced antinociception via the naloxone-sensitive sigma receptor in the mouse. | European journal of pharmacology 20071001 |
| (+)-Morphine and (-)-morphine stereoselectively attenuate the (-)-morphine-produced tail-flick inhibition via the naloxone-sensitive sigma receptor in the ventral periaqueductal gray of the rat. | European journal of pharmacology 20070924 |
| Differential effects of sigma1 receptor blockade on self-administration and conditioned reinstatement motivated by cocaine vs natural reward. | Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20070901 |
| Involvement of sigma-1 receptor modulation in the antidepressant action of venlafaxine. | Neuroscience letters 20070615 |
| Involvement of the sigma1 receptor in inhibiting activity of fluvoxamine on marble-burying behavior: comparison with paroxetine. | European journal of pharmacology 20070601 |
| dextro-Morphine attenuates the morphine-produced conditioned place preference via the sigma(1) receptor activation in the rat. | European journal of pharmacology 20070521 |
| Dextromethorphan attenuates trimethyltin-induced neurotoxicity via sigma1 receptor activation in rats. | Neurochemistry international 20070501 |
| Novel sigma receptor ligands: synthesis and biological profile. | Journal of medicinal chemistry 20070308 |
| 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 |
| Sigma-1 receptor activation prevents intracellular calcium dysregulation in cortical neurons during in vitro ischemia. | The Journal of pharmacology and experimental therapeutics 20061201 |
| The anti-amnesic and neuroprotective effects of donepezil against amyloid beta25-35 peptide-induced toxicity in mice involve an interaction with the sigma1 receptor. | British journal of pharmacology 20061201 |
| Sigma1 receptor ligands and related neuroactive steroids interfere with the cocaine-induced state of memory. | Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20060701 |
| Cocaine-induced HIV-1 expression in microglia involves sigma-1 receptors and transforming growth factor-beta1. | International immunopharmacology 20060601 |
| Intrathecal treatment with sigma1 receptor antagonists reduces formalin-induced phosphorylation of NMDA receptor subunit 1 and the second phase of formalin test in mice. | British journal of pharmacology 20060601 |
| 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 |
| Interaction with sigma(1) protein, but not N-methyl-D-aspartate receptor, is involved in the pharmacological activity of donepezil. | The Journal of pharmacology and experimental therapeutics 20060501 |
| Sigma receptor ligands protect human retinal cells against oxidative stress. | Neuroreport 20060227 |
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| Presynaptic modulation of synaptic transmission by pregnenolone sulfate as studied by optical recordings. | Journal of neurophysiology 20051201 |
| Cocaine and sigma-1 receptors modulate HIV infection, chemokine receptors, and the HPA axis in the huPBL-SCID model. | Journal of leukocyte biology 20051201 |
| Neuroactive steroids protect retinal pigment epithelium against oxidative stress. | Neuroreport 20050801 |
| The dextromethorphan analog dimemorfan attenuates kainate-induced seizures via sigma1 receptor activation: comparison with the effects of dextromethorphan. | British journal of pharmacology 20050401 |
| Sigma receptor antagonists inhibit human lens cell growth and induce pigmentation. | Investigative ophthalmology & visual science 20050401 |
| Phenytoin differentially modulates the affinity of agonist and antagonist ligands for sigma 1 receptors of guinea pig brain. | Synapse (New York, N.Y.) 20050301 |
| Effects of neurosteroids on ischemia-reperfusion injury in the rat retina: role of sigma1 recognition sites. | European journal of pharmacology 20040913 |
| The sigma1 (sigma1) receptor activation is a key step for the reactivation of cocaine conditioned place preference by drug priming. | Psychopharmacology 20040901 |
| Small molecule antagonists of the sigma-1 receptor cause selective release of the death program in tumor and self-reliant cells and inhibit tumor growth in vitro and in vivo. | Cancer research 20040715 |
| Role of NMDA receptor subtypes in the induction of catalepsy and increase in Fos protein expression after administration of haloperidol. | Brain research 20040611 |
| Cocaine modulates cytokine and enhances tumor growth through sigma receptors. | Journal of neuroimmunology 20040201 |
| Antitussive activity of sigma-1 receptor agonists in the guinea-pig. | British journal of pharmacology 20040101 |
| Sigma 1 receptor-related neuroactive steroids modulate cocaine-induced reward. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20030501 |
| Sigma sites mediate DTG-evoked hypothermia in rats. | Pharmacology, biochemistry, and behavior 20021101 |
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| Characterization of two novel sigma receptor ligands: antidystonic effects in rats suggest sigma receptor antagonism. | European journal of pharmacology 19950714 |
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