Ifenprodil hemitartrate | CAS#23210-58-4

MedKoo Cat#: 329680 | Name: Ifenprodil hemitartrate

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ifenprodil is an inhibitor of the NMDA receptor, specifically of GluN1 (glycine-binding NMDA receptor subunit 1) and GluN2B (glutamate-binding NMDA receptor subunit 2) subunits. Additionally, ifenprodil inhibits GIRK channels, and interacts with alpha1 adrenergic, serotonin, and sigma receptors.

Chemical Structure

Ifenprodil hemitartrate

CAS#23210-58-4 (tartrate)

Theoretical Analysis

MedKoo Cat#: 329680

Name: Ifenprodil hemitartrate

CAS#: 23210-58-4 (tartrate)

Chemical Formula: C46H60N2O10

Exact Mass:

Molecular Weight: 800.99

Elemental Analysis: C, 68.98; H, 7.55; N, 3.50; O, 19.97

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 350.00	2 Weeks
100mg	USD 650.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

23210-58-4 (tartrate) 23210-56-2 (free base) 66157-43-5 (tartrate)

Synonym

Ifenprodil; Ifenprodil hemitartrate; Ifenprodil tartrate; RC 61-91; RC-61-91; RC61-91; RC 6191; RC61-91; RC6191;

IUPAC/Chemical Name

4-(2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl)phenol; (2R,3R)-2,3-dihydroxysuccinate (2:1)

InChi Key

DMPRDSPPYMZQBT-CEAXSRTFSA-N

InChi Code

InChI=1S/2C21H27NO2.C4H6O6/c2*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;5-1(3(7)8)2(6)4(9)10/h2*2-10,16,18,21,23-24H,11-15H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t;;1-,2-/m..1/s1

SMILES Code

OC1=CC=C(C(O)C(N2CCC(CC3=CC=CC=C3)CC2)C)C=C1.OC4=CC=C(C(O)C(N5CCC(CC6=CC=CC=C6)CC5)C)C=C4.O=C(O)[C@H](O)[C@@H](O)C(O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

NMDA receptors are multimeric ionotropic glutamate receptors composed of four subunits. GluN1 is obligate for functional expression. Other subunits include GluN2A, GluN2B, and the more recently discovered GluN3 subunits. Ifenprodil selectively blocks NMDA receptors containing the GluN2B subunit.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ifenprodil tartrate is a typical noncompetitive NMDA receptor antagonist. Ifenprodil tartrate exerts high affinity at NR1A/NR2B receptors (IC50=0.34 μM) over 400-fold than at NR1A/NR2A receptors (IC50=146 μM). Ifenprodil tartrate inhibits GIRK (Kir3), reduces inward currents through the basal GIRK activity. Ifenprodil tartrate has the potential to be a cerebral vasodilator.

In vitro activity:

In experiments with "younger" neurons, 6-8 days in vitro (6-8 DIV), in which the NR2A-containing NMDAR expression is low, ifenprodil, an inhibitor of NR2B-containing NMDAR, completely prevented DCD whereas PEAQX, another NMDAR antagonist that preferentially interacts with NR2A-NMDAR, was without effect. This suggests that ifenprodil, Ro 25-6981, and Co 101244 inhibit NCX(rev). The ability of ifenprodil to inhibit NCX(rev) correlates with its efficacy in preventing DCD and emphasizes an important role of NCX(rev) in DCD. Reference: Neuropharmacology. 2012 Nov;63(6):974-82. https://pubmed.ncbi.nlm.nih.gov/22820271/

In vivo activity:

Ifenprodil treatment also reduced the frequency [F(1,10) = 31.756; p < .001; ηp2 = 0.761] (Figure 2D) and duration [F(1,10) = 10.075; p = 0.010; ηp2 = 0.502] (Figure 2E) of anogenital sniffing. Planned comparisons show that ifenprodil treatment reduced the frequency of anogenital sniffing in both SAC [F(1,5) = 17.043; p = 0.009; ηp2 = 0.773] and PAE rats [F(1,5) = 15.180; p = 0.011; ηp2 = 0.752], while ifenprodil treatment only reduced the duration of anogenital sniffing in the SAC group [F(1,5) = 11.140; p = 0.021; ηp2 = 0.021] (PAE: p > 0.22). Ifenprodil reduced the frequency of wrestling [F(1,10) = 5.735; p = 0.038; ηp2 = 0.364] (Figure 2F), which planned comparison show was significant in PAE animals [F(1,5) = 15.638; p = 0.011; ηp2 = 0.758] and not in SAC controls (p > 0.89). Reference: Behav Brain Res. 2017 Mar 1;320:1-11. https://pubmed.ncbi.nlm.nih.gov/27888019/

	Solvent	mg/mL	mM
Solubility
	DMF	50.0	62.42
	DMSO	208.3	260.09
	Ethanol	46.0	57.43
	PBS (pH 7.2)	1.0	2.50

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 800.99 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	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Amico-Ruvio SA, Paganelli MA, Myers JM, Popescu GK. Ifenprodil effects on GluN2B-containing glutamate receptors. Mol Pharmacol. 2012 Dec;82(6):1074-81. doi: 10.1124/mol.112.078998. Epub 2012 Aug 30. PMID: 22936815; PMCID: PMC3502619. 2. Brittain MK, Brustovetsky T, Brittain JM, Khanna R, Cummins TR, Brustovetsky N. Ifenprodil, a NR2B-selective antagonist of NMDA receptor, inhibits reverse Na+/Ca2+ exchanger in neurons. Neuropharmacology. 2012 Nov;63(6):974-82. doi: 10.1016/j.neuropharm.2012.07.012. Epub 2012 Jul 20. PMID: 22820271; PMCID: PMC3427421. 3. Bird CW, Barto D, Magcalas CM, Rodriguez CI, Donaldson T, Davies S, Savage DD, Hamilton DA. Ifenprodil infusion in agranular insular cortex alters social behavior and vocalizations in rats exposed to moderate levels of ethanol during prenatal development. Behav Brain Res. 2017 Mar 1;320:1-11. doi: 10.1016/j.bbr.2016.11.036. Epub 2016 Nov 22. PMID: 27888019; PMCID: PMC5239726. 4. Feng H, Chen Z, Wang G, Zhao X, Liu Z. Effect of the ifenprodil administered into rostral anterior cingulate cortex on pain-related aversion in rats with bone cancer pain. BMC Anesthesiol. 2016 Nov 21;16(1):117. doi: 10.1186/s12871-016-0283-1. PMID: 27871230; PMCID: PMC5117499.

In vitro protocol:

In vivo protocol:

1. Bird CW, Barto D, Magcalas CM, Rodriguez CI, Donaldson T, Davies S, Savage DD, Hamilton DA. Ifenprodil infusion in agranular insular cortex alters social behavior and vocalizations in rats exposed to moderate levels of ethanol during prenatal development. Behav Brain Res. 2017 Mar 1;320:1-11. doi: 10.1016/j.bbr.2016.11.036. Epub 2016 Nov 22. PMID: 27888019; PMCID: PMC5239726. 2. Feng H, Chen Z, Wang G, Zhao X, Liu Z. Effect of the ifenprodil administered into rostral anterior cingulate cortex on pain-related aversion in rats with bone cancer pain. BMC Anesthesiol. 2016 Nov 21;16(1):117. doi: 10.1186/s12871-016-0283-1. PMID: 27871230; PMCID: PMC5117499.