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Merck
CN

C104

(±)-CPP

solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C8H17N2O5P
CAS Number:
Molecular Weight:
252.20
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
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form

solid

Quality Level

color

white

solubility

H2O: 99.2 mg/mL, ethanol: insoluble

SMILES string

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)

InChI key

CUVGUPIVTLGRGI-UHFFFAOYSA-N

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

Biochem/physiol Actions

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.

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Hygroscopic


pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves



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Thien-Tri Cung et al.
The New England journal of medicine, 373(11), 1021-1031 (2015-09-01)
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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



Global Trade Item Number

SKUGTIN
C104-5MG04061833006085
C104-100MG04061833006061
C104-25MG04061833006078