Saltar al contenido
Merck

I2892

Sigma-Aldrich

Ifenprodil (+)-tartrate salt

Sinónimos:

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

Iniciar sesiónpara Ver la Fijación de precios por contrato y de la organización


About This Item

Fórmula lineal:
(C21H27NO2)2 · C4H6O6
Número de CAS:
Peso molecular:
800.98
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

storage temp.

room temp

Quality Level

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

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Elija entre una de las versiones más recientes:

Certificados de análisis (COA)

Lot/Batch Number

¿No ve la versión correcta?

Si necesita una versión concreta, puede buscar un certificado específico por el número de lote.

¿Ya tiene este producto?

Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

Los clientes también vieron

Slide 1 of 1

1 of 1

Inhibition of G protein-activated inwardly rectifying K+ channels by ifenprodil
Kobayashi T, et al.
Neuropsychopharmacology, 31(3), 516-516 (2006)
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
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)
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

Artículos

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

Nuestro equipo de científicos tiene experiencia en todas las áreas de investigación: Ciencias de la vida, Ciencia de los materiales, Síntesis química, Cromatografía, Analítica y muchas otras.

Póngase en contacto con el Servicio técnico