threo Ifenprodil hemitartrateCAS# 1312991-83-5 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 1312991-83-5 | SDF | Download SDF |
| PubChem ID | 90488783 | Appearance | Powder |
| Formula | C92H120N4O20 | M.Wt | 1602.0 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 25 mM in water and to 100 mM in DMSO | ||
| Chemical Name | 4-[(1S,2S)-2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl]phenol;4-[(1R,2R)-2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl]phenol;2,3-dihydroxybutanedioic acid | ||
| SMILES | CC(C(C1=CC=C(C=C1)O)O)N2CCC(CC2)CC3=CC=CC=C3.CC(C(C1=CC=C(C=C1)O)O)N2CCC(CC2)CC3=CC=CC=C3.CC(C(C1=CC=C(C=C1)O)O)N2CCC(CC2)CC3=CC=CC=C3.CC(C(C1=CC=C(C=C1)O)O)N2CCC(CC2)CC3=CC=CC=C3.C(C(C(=O)O)O)(C(=O)O)O.C(C(C(=O)O)O)(C(=O)O)O | ||
| Standard InChIKey | MMUFFGLAKFWLGJ-RRQZTXAJSA-N | ||
| Standard InChI | InChI=1S/4C21H27NO2.2C4H6O6/c4*1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17;2*5-1(3(7)8)2(6)4(9)10/h4*2-10,16,18,21,23-24H,11-15H2,1H3;2*1-2,5-6H,(H,7,8)(H,9,10)/t4*16-,21+;;/m1100../s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Potent σ receptor agonist (Ki values are 59.1 and 2 nM for σ1 and σ2 receptors respectively) and NR2B subunit-selective NMDA receptor antagonist (IC50 values are 0.22 and 324.8 μM at NR2B and NR2A respectively). Displays ~8-fold reduced affinity at α-adrenoceptors compared to Ifenprodil. Inhibits the hERG potassium channel (IC50 = 88 nM) and exhibits antiarrhythmic activity in vivo. |
threo Ifenprodil hemitartrate Dilution Calculator
threo Ifenprodil hemitartrate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 0.6242 mL | 3.1211 mL | 6.2422 mL | 12.4844 mL | 15.6055 mL |
| 5 mM | 0.1248 mL | 0.6242 mL | 1.2484 mL | 2.4969 mL | 3.1211 mL |
| 10 mM | 0.0624 mL | 0.3121 mL | 0.6242 mL | 1.2484 mL | 1.5605 mL |
| 50 mM | 0.0125 mL | 0.0624 mL | 0.1248 mL | 0.2497 mL | 0.3121 mL |
| 100 mM | 0.0062 mL | 0.0312 mL | 0.0624 mL | 0.1248 mL | 0.1561 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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sigma(2)-receptor ligand-mediated inhibition of inwardly rectifying K(+) channels in the heart.[Pubmed:17460149]
J Pharmacol Exp Ther. 2007 Jul;322(1):341-50.
The sigma(2)-receptor agonist, ifenprodil, was suggested as an inhibitor of G protein-coupled inwardly rectifying potassium channels. Nevertheless, an analysis of the role of sigma(2) receptors in cardiac electrophysiology has never been done. This work aims i) to identify the roles of cardiac sigma(2) receptors in the regulation of cardiac K(+) channel conductances and ii) to check whether sigma(2)-receptor agonists exhibit class III antiarrhythmic properties. The sigma(2)-receptor agonists ifenprodil, threo-ifenprodil, LNP250A [threo-8-[1-(4-hydroxyphenyl)-1-hydroxy-propan-2-yl]-1-phenyl-1,3,8-triazaspiro[4 ,5]decane-4-one] (a derivative of ifenprodil devoid of alpha(1)-adrenergic and N-methyl-d-aspartate glutamate receptor-blocking properties), and 1,3-di(2-tolyl)guanidine were used to discriminate the effects linked to sigma(2) receptors from those of the sigma(1) subtype, induced by (+/-)-N-allylnormetazocine (SKF-10,047). The sigma(2)-receptor antagonist 3-alpha-tropanyl-2(pCl-phenoxy)butyrate (SM-21) was employed to characterize sigma(2)-mediated effects in patch-clamp experiments. In rabbits, all sigma(2)-receptor agonists reduced phenylephrine-induced cardiac arrhythmias. They prolonged action potential duration in rabbit Purkinje fibers and reduced human ether-a-go-go-related gene (HERG) K(+) currents. (+)-SKF-10,047 was completely inactive in the last two tests. The effects of threo-ifenprodil were not antagonized by SM-21. In HERG-transfected COS-7 cells, SM-21 potentiated the ifenprodil-induced blockade of the HERG current. These data suggest that sigma(2)-receptor ligands block I(Kr) and that this effect could explain part of the antiarrhythmic properties of this ligands family. Nevertheless, an interaction with HERG channels not involving sigma(2) receptors seems to share this pharmacological property. This work shows for the first time that particular caution has to be taken toward ligands with affinity for sigma(2) receptors. The repolarization prolongation and the early-afterdepolarization can be responsible for "torsades de pointe" and sudden cardiac death.
Antagonist properties of the stereoisomers of ifenprodil at NR1A/NR2A and NR1A/NR2B subtypes of the NMDA receptor expressed in Xenopus oocytes.[Pubmed:8838458]
Eur J Pharmacol. 1996 Jan 25;296(2):209-13.
The NMDA receptor antagonist ifenprodil contains two asymmetric centres which give rise to four stereoisomeric forms of this molecule. The inhibitory effects of each of these stereoisomers on recombinant NMDA receptors expressed from NR1A/NR2A and NR1A/NR2B subunit combinations were studied in Xenopus oocytes by voltage-clamp recording. All four ifenprodil stereoisomers were potent antagonists at NR1A/NR2B (IC50 < 0.8 microM), but weak antagonists at NR1A/NR2A receptors (IC50 > 100 microM). In heteromeric NR1A/NR2B receptors, (+) erythro- and (-) threo-ifenprodil (IC50 0.21 and 0.22 microM, respectively) were about 4 times more potent than (-) erythro- and (+) threo-ifenprodil (IC50 0.81 and 0.76, respectively). These results show that the stereoisomers of ifenprodil exhibit a weak though significant stereoselectivity at the NR1A/NR2B NMDA receptor subtype.
Interactions of erythro-ifenprodil, threo-ifenprodil, erythro-iodoifenprodil, and eliprodil with subtypes of sigma receptors.[Pubmed:7737340]
Eur J Pharmacol. 1995 Feb 6;273(3):307-10.
Observations of sigma (sigma) receptor heterogeneity have prompted interest in identifying ligands for sigma receptor subtypes. Selective ligands for the sigma-2 are unavailable, but [3H]ifenprodil labels sigma-2 sites. Therefore, isomers and analogues of ifenprodil were compared as potential sigma-2 ligands. Threo-ifenprodil and erythro-ifenprodil had high affinity (Ki congruent to 2 nM) for sigma-2 sites; erythro-iodoifenprodil had moderate affinity (Ki congruent to 46 nM); eliprodil had lowest affinity (Ki congruent to 630 nM). Threo-ifenprodil, which has less affinity for alpha 1-adrenoceptors than erythro-ifenprodil, was slightly more selective than erythro-ifenprodil for sigma-2 sites. These results identify threo-ifenprodil as potentially useful for studies of sigma-2 receptors.
