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I2892

Sigma-Aldrich

Ifenprodil (+)-tartrate salt

Synonyme(s) :

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

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About This Item

Formule linéaire :
(C21H27NO2)2 · C4H6O6
Numéro CAS:
23210-58-4
Poids moléculaire :
800.98
Numéro CE :
245-493-5
Numéro MDL:
MFCD01529999
Code UNSPSC :
12352200
ID de substance PubChem :
24278826
Nomenclature NACRES :
NA.77

Température de stockage

room temp

Niveau de qualité

200

Chaîne SMILES 

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)

Clé InChI

DMPRDSPPYMZQBT-UHFFFAOYSA-N

Informations sur le gène

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

Description générale

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

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
085M4179V
049M4075V
098M4086V
13171116
085M4178V

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Ifenprodil for the treatment of flashbacks in adolescent female posttraumatic stress disorder patients with a history of abuse
Sasaki T, et al.
Psychotherapy and Psychosomatics, 82(5), 344-345 (2013)
Anti?epileptic effect of ifenprodil on neocortical pyramidal neurons in patients with malformations of cortical development
Wang X, et al.
Experimental and Therapeutic Medicine, 14(6), 5757-5766 (2017)
Pieter B Burger et al.
Molecular pharmacology, 82(2), 344-359 (2012-05-19)
We have used recent structural advances in our understanding of the N-methyl-d-aspartate (NMDA) receptor amino terminal domain to explore the binding mode of multiple diaryl GluN2B-selective negative allosteric modulators at the interface between the GluN1 and GluN2B amino-terminal domains. We
Matthew K Brittain et al.
Neuropharmacology, 63(6), 974-982 (2012-07-24)
Glutamate-induced delayed calcium dysregulation (DCD) is causally linked to excitotoxic neuronal death. The mechanisms of DCD are not completely understood, but it has been proposed that the excessive influx of external Ca(2+) is essential for DCD. The NMDA-subtype of glutamate
J Kurihara et al.
European journal of pharmacology, 190(1-2), 23-30 (1990-11-06)
Baroreflex sensitivity assessed from the phenylephrine-induced reflex bradycardia was significantly decreased following 5 min global incomplete cerebral ischemia in pentobarbitalized dogs. Although bilateral vagotomy in the cervical region decreased baroreflex sensitivity by about 50% in sham-operated animals, it hardly affected
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