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Merck

I2892

Ifenprodil (+)-tartrate salt

NMDA antagonist

Sinónimos:

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

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Fórmula lineal:
(C21H27NO2)2 · C4H6O6
Número CAS:
23210-58-4
Peso molecular:
800.98
NACRES:
NA.77
PubChem Substance ID:
24278826
UNSPSC Code:
12352200
EC Number:
245-493-5
MDL number:
MFCD01529999
Quality level:
200

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Nombre del producto

Ifenprodil (+)-tartrate salt,

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)

Categorías relacionadas

General description

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

Application

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

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000479050
0000479050
0000445537
0000350693
0000350693

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Inhibition of G protein-activated inwardly rectifying K+ channels by ifenprodil
Kobayashi T, et al.
Neuropsychopharmacology, 31(3), 516-516 (2006)
NMDA receptor antagonists attenuate intrathecal morphine-induced pruritus through ERK phosphorylation
Shen L, et al.
Molecular Brain, 11(1), 35-35 (2018)
Involvement of NMDA receptor subtypes in cortical spreading depression in rats assessed by fMRI
Shatillo A, et al.
Neuropharmacology, 93, 164-170 (2015)
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
B L Chenard et al.
Current pharmaceutical design, 5(5), 381-404 (1999-04-24)
In the late 1980s, a new class of N-methyl-D-aspartate (NMDA) receptor antagonists, exemplified by the phenylethanolamine ifenprodil (1), was identified. Initially, the mechanism of action of ifenprodil was a mystery as it was not a competitive antagonist at the glutamate
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