threo Ifenprodil hemitartrate

Name: threo Ifenprodil hemitartrate
Brand: Tocris Bioscience
SKU: 2892

Tocris Bioscience a Bio-Techne Brand

Catalog # 2892

Citations (2)

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Key Product Details

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)
Molecular Weight:	400.49

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Biological Activity for threo Ifenprodil hemitartrate

threo Ifenprodil hemitartrate is a potent σ receptor agonist (K_i 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 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	2.50 mL	12.48 mL	24.97 mL
5 mM	0.50 mL	2.50 mL	4.99 mL
10 mM	0.25 mL	1.25 mL	2.50 mL
50 mM	0.05 mL	0.25 mL	0.50 mL

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References for threo Ifenprodil hemitartrate

References are publications that support the biological activity of the product.

Monassier σ₂-receptor ligand-mediated inhibition of inwardly rectifying K⁺channels in the heart. J.Pharmacol.Exp.Ther. 2007 PMID: 17460149
Avenet 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. 1996 PMID: 8838458
Hashimoto and London Interactions of erythro-ifenprodil, threo-ifenprodil and erythro-iodoifenprodil, and eliprodil with subtypes of σ receptors. Eur.J.Pharmacol. 1995 PMID: 7737340

Citations for threo Ifenprodil hemitartrate (2)

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Citations are publications that use Bio-Techne products. Selected citations for threo Ifenprodil hemitartrate include:

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
Gasperini et al. (2015) Prion protein and copper cooperatively protect neurons by modulating NMDA receptor through S-nitrosylation. Sci Rep. 22:772
PMID: 25490055

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