A competitive NMDA antagonist
Related Products
Isomer(s)
14539D-AP5
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DL-AP5

Item No. 14540

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-phosphono-norvaline
CAS Number
76326-31-3
Synonyms
  • DL-2-Amino-5-Phosphonovaleric acid
  • 2-APV
Molecular Formula
C5H12NO5P
Formula Weight
197.1
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
OP(CCCC(C(O)=O)N)(O)=O
InChi Code
InChI=1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)
InChi Key
VOROEQBFPPIACJ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $66

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    10 mg

    $113

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    25 mg

    $264

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    50 mg

    $396

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    Product Description

    DL-AP5 is the racemic version of the selective N-methyl-D-aspartate (NMDA) receptor antagonist, D-AP5 (Item No. 14539).1 Whereas D-AP5 is the active (−)-stereoisomer that competitively inhibits the glutamate binding site of NMDA receptors (Kd = 1.4 μM), the (+)-isomer (L-AP5) demonstrates considerably less potent NMDA receptor antagonist activity.1 AP5 has been widely used to study the activity of NMDA receptors particularly in regard to researching synaptic plasticity, learning, and memory.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Evans, R.H., Francis, A.A., Jones, A.W., et al. The effects of a series of ω-phosphonic α-carboxylic amino acids on electrically evoked and excitant amino acid-induced responses in isolated spinal cord preparations. Br. J. Pharmacol. 75(1), 65-75 (1982).

    2. Morris, R.J. Synaptic plasticity and learning: Selective impairment of learning rats and blockade of long-term potentiation in vivo by the N-methyl-D-aspartate receptor antagonist AP5. J. Neurosci. 9(9), 3040-3057 (1989).