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C104

Sigma-Aldrich

(±)-CPP

solid

Synonyme(s) :

(±)-3-(2-Carboxypiperazin-4-yl)propyl-1-phosphonic acid

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About This Item

Formule empirique (notation de Hill):
C8H17N2O5P
Numéro CAS:
100828-16-8
Poids moléculaire :
252.20
Numéro MDL:
MFCD00055136
Code UNSPSC :
12352200
ID de substance PubChem :
24277958
Nomenclature NACRES :
NA.77

Forme

solid

Couleur

white

Solubilité

H2O: 99.2 mg/mL
ethanol: insoluble

Chaîne SMILES 

OC(=O)C1CN(CCCP(O)(O)=O)CCN1

InChI

1S/C8H17N2O5P/c11-8(12)7-6-10(4-2-9-7)3-1-5-16(13,14)15/h7,9H,1-6H2,(H,11,12)(H2,13,14,15)

Clé InChI

CUVGUPIVTLGRGI-UHFFFAOYSA-N

Informations sur le gène

human ... GRIN1(2902) , GRIN2A(2903) , GRIN2B(2904) , GRIN2C(2905) , GRIN2D(2906) , GRINA(2907)
rat ... Grin2a(24409)

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Application

(±)-CPP has been used as an uncompetitive NMDA receptor antagonist:
  • to study its effects on blood glucose in mice
  • in electrophysiological recording in mouse brain slices
  • in electrophysiological recording in rat hippocampal pyramidal neurons

Actions biochimiques/physiologiques

3-(2-carboxypiperazin-4yl) propyl-1-phosphonic acid (CPP) is a potent, competitive, and selective N-methyl-D-aspartate (NMDA) receptor antagonist. It is an analog of 2-amino-7-phosphonoheptanoic acid. CPP shows anticonvulusant and antinociceptive activity.

Attention

Hygroscopic

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Consulter la Bibliothèque de documents

Thien-Tri Cung et al.
The New England journal of medicine, 373(11), 1021-1031 (2015-09-01)
Experimental and clinical evidence suggests that cyclosporine may attenuate reperfusion injury and reduce myocardial infarct size. We aimed to test whether cyclosporine would improve clinical outcomes and prevent adverse left ventricular remodeling. In a multicenter, double-blind, randomized trial, we assigned
Mohammadali Foroozandeh et al.
Magnetic resonance in chemistry : MRC, 53(11), 894-900 (2015-08-21)
Resolution enhancement is a long-sought goal in NMR spectroscopy. In conventional multidimensional NMR experiments, such as the (1) H-(13) C HSQC, the resolution in the indirect dimensions is typically 100 times lower as in 1D spectra because it is limited
Anita E Autry et al.
Nature, 475(7354), 91-95 (2011-06-17)
Clinical studies consistently demonstrate that a single sub-psychomimetic dose of ketamine, an ionotropic glutamatergic NMDAR (N-methyl-D-aspartate receptor) antagonist, produces fast-acting antidepressant responses in patients suffering from major depressive disorder, although the underlying mechanism is unclear. Depressed patients report the alleviation
Wayne W Tschetter et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(12), 5362-5366 (2013-03-22)
We previously reported in adult mice that visuomotor experience during monocular deprivation (MD) augmented enhancement of visual-cortex-dependent behavior through the non-deprived eye (NDE) during deprivation, and enabled enhanced function to persist after MD. We investigated the physiological substrates of this
Neil Schwartz et al.
Neuron, 70(3), 455-467 (2011-05-11)
In the developing Xenopus tadpole, conditioning with 20 min of visual stimulation leads to increased proBDNF protein levels in the tectum measured 4 hr later. Following conditioning, the ability to induce direction selectivity in tectal neurons, as well as both
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