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I2892

Sigma-Aldrich

Ifenprodil (+)-tartrate salt

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

Quality Level

200

storage temp.

room temp

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. 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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Pallab Bhattacharya et al.
Medical hypotheses, 79(4), 516-518 (2012-08-10)
Owing to the intricate and multifaceted pathology of cerebral stroke, multiple drug therapy had long been suggested for effective stroke treatment. Therefore, the development of a potential new combination of drug is necessitated which can bring about desirable improved neuroprotection
Ifenprodil and SL 82.0715 are antagonists at the polyamine site of the N-methyl-D-aspartate (NMDA) receptor.
C Carter et al.
European journal of pharmacology, 164(3), 611-612 (1989-05-30)
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)
Ifenprodil for emotional incontinence in patients with vascular dementia: two case reports.
Akira Kishimoto et al.
Journal of clinical psychopharmacology, 33(1), 143-145 (2013-01-05)
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