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I2892

Sigma-Aldrich

Ifenprodil (+)-tartrate salt

Synonym(s):

α-(4-Hydroxyphenyl)-β-methyl-4-benzyl-1-piperidineethanol (+)-tartrate salt

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10 MG
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About This Item

Linear Formula:
(C21H27NO2)2 · C4H6O6
CAS Number:
23210-58-4
Molecular Weight:
800.98
EC Number:
245-493-5
MDL number:
MFCD01529999
UNSPSC Code:
12352200
PubChem Substance ID:
24278826
NACRES:
NA.77

¥14,900

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storage temp.

room temp

Quality Level

200

SMILES string

OC(C(O)C(O)=O)C(O)=O.CC(C(O)c1ccc(O)cc1)N2CCC(CC2)Cc3ccccc3.CC(C(O)c4ccc(O)cc4)N5CCC(CC5)Cc6ccccc6

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)

InChI key

DMPRDSPPYMZQBT-UHFFFAOYSA-N

Gene Information

human ... GRIN1(2902) , GRIN2A(2903) , GRIN2B(2904) , GRIN2C(2905) , GRIN2D(2906) , GRINA(2907)

General description

Ifenprodil is a phenylethanolamine, which stimulates blood circulation. It has anticonvulsant and antinociceptive properties.[1] Ifenprodil is used to treat posttraumatic stress disorder,[2] cerebrovascular diseases and peripheral arterial obliterative disease.[1] It blocks G protein-coupled inwardly-rectifying potassium channels (GIRKs) and interacts with α1 adrenergic, N-methyl-D-aspartate and serotonin receptors.[1]

Application

Ifenprodil (+)-tartrate salt has been used:
  • to test the action in a KCl-induced cortical spreading depression (CSD) animal[3]
  • to study its effects on electrophysiological properties and spontaneous spikes in neocortical pyramidal cells[4]
  • to investigate its therapeutic effects[5]

Biochem/physiol Actions

NMDA antagonist acting at the polyamine site; neuroprotective agent; α-adrenergic central and peripheral vasodilator; α2 adrenergic receptor ligand.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate Receptors (Ion Channel Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

I2892-VAR:
I2892-25MG-PW:
I2892-10MG-PW:
I2892-25MG:
I2892-10MG:
I2892-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000350693
0000350693
0000209959
0000145807
0000209959

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Kenneth R Tovar et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 32(23), 8065-8073 (2012-06-08)
The amino-terminal domains of NMDA receptor subunits are important for receptor assembly and desensitization, and incorporate the high-affinity binding sites for zinc and ifenprodil. These amino-terminal ligands are thought of as subunit-specific receptor inhibitors. However, multiple NMDA receptor subtypes contribute
Inhibition of G protein-activated inwardly rectifying K+ channels by ifenprodil
Kobayashi T, et al.
Neuropsychopharmacology, 31(3), 516-516 (2006)
Involvement of NMDA receptor subtypes in cortical spreading depression in rats assessed by fMRI
Shatillo A, et al.
Neuropharmacology, 93, 164-170 (2015)
NMDA receptor antagonists attenuate intrathecal morphine-induced pruritus through ERK phosphorylation
Shen L, et al.
Molecular Brain, 11(1), 35-35 (2018)
Austen J Milnerwood et al.
Neurobiology of disease, 48(1), 40-51 (2012-06-07)
We recently reported evidence for disturbed synaptic versus extrasynaptic NMDAR transmission in the early pathogenesis of Huntington's disease (HD), a late-onset neurodegenerative disorder caused by CAG repeat expansion in the gene encoding huntingtin. Studies in glutamatergic cells indicate that synaptic
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