threo Ifenprodil hemitartrate

Discontinued Product

threo Ifenprodil hemitartrate (Cat. No. 2892) has been withdrawn from sale for commercial reasons.
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)
Citations (2)
Literature (5)

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
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.

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

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Keywords: threo Ifenprodil hemitartrate, threo Ifenprodil hemitartrate supplier, NR2B, selective, NMDA, antagonists, receptors, s, σ, sigma, agonist, ionotropic, glutamate, iGluR, GluN2B, Sigma-Related, Receptors, 2892, Tocris Bioscience

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

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Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!

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