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(±)-CPP

Name: (±)-CPP
Brand: SIGMA

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

NACRES:

NA.77

PubChem Substance ID:

24277958

UNSPSC Code:

12352200

MDL number:

MFCD00055136

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Properties

form

solid

Quality Segment

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)

Description

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

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This Item	D127	G1501	G1626
Sigma-Aldrich C104 (±)-CPP	Sigma-Aldrich D127 Dextrorphan tartrate	Sigma-Aldrich G1501 L-Glutamic acid potassium salt monohydrate	Sigma-Aldrich G1626 L-Glutamic acid monosodium salt hydrate
Quality Level 100	Quality Level 200	Quality Level 300	Quality Level 300
form solid	form powder	form powder	form powder
Gene Information human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRINA(2907) rat ... Grin2a(24409)	Gene Information human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRINA(2907)	Gene Information human ... GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK4(2900), GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRIN3A(116443), GRIN3B(116444), GRINA(2907) mouse ... GRIK1(14805), GRIK2(14806), GRIK3(14807), GRIK4(110637), GRIN1(14810), GRIN2A(14811), GRIN2B(14812), GRIN2C(14813), GRIN2D(14814), GRIN3A(242443), GRIN3B(170483), GRINA(66168) rat ... GRIK1(29559), GRIK2(54257), GRIK3(298521), GRIK4(24406), GRIN1(24408), GRIN2A(24409), GRIN2B(24410), GRIN2C(24411), GRIN2D(24412), GRIN3A(191573), GRIN3B(170796), GRINA(266668)	Gene Information human ... GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK4(2900), GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRIN3A(116443), GRIN3B(116444), GRINA(2907) mouse ... GRIK1(14805), GRIK2(14806), GRIK3(14807), GRIK4(110637), GRIN1(14810), GRIN2A(14811), GRIN2B(14812), GRIN2C(14813), GRIN2D(14814), GRIN3A(242443), GRIN3B(170483), GRINA(66168) rat ... GRIK1(29559), GRIK2(54257), GRIK3(298521), GRIK4(24406), GRIN1(24408), GRIN2A(24409), GRIN2B(24410), GRIN2C(24411), GRIN2D(24412), GRIN3A(191573), GRIN3B(170796), GRINA(266668)
color white	color white	color white	color white to off-white
solubility H₂O: 99.2 mg/mL, ethanol: insoluble	solubility H₂O: >10 mg/mL	solubility -	solubility -