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C104

Sigma-Aldrich

(±)-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:
100828-16-8
Molecular Weight:
252.20
MDL number:
MFCD00055136
UNSPSC Code:
12352200
PubChem Substance ID:
24277958
NACRES:
NA.77

form

solid

Quality Level

100

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

Gene Information

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

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.

Caution

Hygroscopic

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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