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Submit Reviewthreo Ifenprodil hemitartrate
Description: GluN2B-selective NMDA antagonist; also σ agonist
Chemical Name: (1S*,2S*)-threo-2-(4-Benzylpiperidino)-1-(4-hydroxyphenyl)-1-propanol hemitartrate
Purity: ≥98% (HPLC)
Biological Activity for threo Ifenprodil hemitartrate
threo Ifenprodil hemitartrate is a potent σ receptor agonist (Ki values are 59.1 and 2 nM for σ1 and σ2 receptors respectively) and GluN2B (formally NR2B) subunit-selective NMDA receptor antagonist (IC50 values are 0.22 and 324.8 μM at GluN2B and GluN2A respectively). Displays ~8-fold reduced affinity at α-adrenoceptors compared to Ifenprodil (Cat.No. 0545). Inhibits the hERG potassium channel (IC50 = 88 nM) and exhibits antiarrhythmic activity in vivo.
Please refer to IUPHAR Guide to Pharmacology for the most recent naming conventions.
Technical Data for threo Ifenprodil hemitartrate
| M. Wt | 400.49 |
| Formula | C21H27NO2.½C4H6O6 |
| Storage | Store at RT |
| Purity | ≥98% (HPLC) |
| PubChem ID | 11957579 |
| InChI Key | DMPRDSPPYMZQBT-UHFFFAOYSA-N |
| Smiles | OC(C=C3)=CC=C3[C@H](O)[C@H](C)N2CCC(CC2)CC1=CC=CC=C1.OC(C=C6)=CC=C6[C@H](O)[C@H](C)N5CCC(CC5)CC4=CC=CC=C4.OC(C=C9)=CC=C9[C@@H](O)[C@@H](C)N8CCC(CC8)CC7=CC=CC=C7.OC(C=C%12)=CC=C%12[C@@H](O)[C@@H](C)N%11CCC(CC%11)CC%10=CC=CC=C%10.O=C(O)C(O)C(O)C(O)=O.O=C(O)C(O)C(O)C(O)=O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for threo Ifenprodil hemitartrate
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 10.01 | 25 | |
| DMSO | 40.05 | 100 |
Preparing Stock Solutions for threo Ifenprodil hemitartrate
The following data is based on the product molecular weight 400.49. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.5 mL | 12.48 mL | 24.97 mL |
| 5 mM | 0.5 mL | 2.5 mL | 4.99 mL |
| 10 mM | 0.25 mL | 1.25 mL | 2.5 mL |
| 50 mM | 0.05 mL | 0.25 mL | 0.5 mL |
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Product Datasheets for threo Ifenprodil hemitartrate
References for threo Ifenprodil hemitartrate
References are publications that support the biological activity of the product.
Hashimoto and London (1995) Interactions of erythro-ifenprodil, threo-ifenprodil and erythro-iodoifenprodil, and eliprodil with subtypes of σ receptors. Eur.J.Pharmacol. 273 307 PMID: 7737340
Avenet et al (1996) Antagonist properties of the stereoisomers of ifenprodil at NR1A/NR2A and NR1A/NR2B subtypes of the NMDA receptor expressed in Xenopus oocytes. Eur.J.Pharmacol. 296 209 PMID: 8838458
Monassier et al (2007) σ2-receptor ligand-mediated inhibition of inwardly rectifying K+channels in the heart. J.Pharmacol.Exp.Ther. 322 341 PMID: 17460149
If you know of a relevant reference for threo Ifenprodil hemitartrate, please let us know.
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2 Citations for threo Ifenprodil hemitartrate
Citations are publications that use Tocris products. Selected citations for threo Ifenprodil hemitartrate include:
Gasperini et al (2015) Prion protein and copper cooperatively protect neurons by modulating NMDA receptor through S-nitrosylation. Sci Rep 22 772 PMID: 25490055
Lassus et al (2018) Glutamatergic and dopaminergic modulation of cortico-striatal circuits probed by dynamic calcium imaging of networks reconstructed in microfluidic chips. Sci Rep 8 17461 PMID: 30498197
Do you know of a great paper that uses threo Ifenprodil hemitartrate from Tocris? Please let us know.
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