A metabotropic glutamate receptor antagonist
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DL-AP3

Item No. 13852

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-phosphono-alanine
CAS Number
5652-28-8
Synonyms
  • DL-2-Amino-3-Phosphonopropionic Acid
  • NSC 30078
Molecular Formula
C3H8NO5P
Formula Weight
169.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 2 mg/ml
SMILES
NC(CP(O)(O)=O)C(O)=O
InChi Code
InChI=1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
InChi Key
LBTABPSJONFLPO-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

    $41

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    100 mg

    $75

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    Product Description

    DL-AP3 is a competitive mGluR1 antagonist that demonstrates a Ki value of 298 μM and an IC50 value of 1mM for rat mGluR1α when challenged with glutamate.1 DL-AP3 can antagonize excitatory amino acid-induced phosphoinositide hydrolysis, induce Ca2+ mobilization in rat hippocampal slices, and inhibit phosphoserine phosphatase in rat brain cortex.2,3 At concentrations from 10-300 μM DL-AP3 has been used to characterize the role of mGluR in long-term potentiation in the hippocampus in a model of learning and memory, the release of glutamate in Parkinson’s disease, and the increased activity of mGluR implicated in fragile X syndrome.4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schoepp, D.D., Jane, D.E., and Monn, J.A. Pharmacological agents acting at subtypes of metabotropic glutamate receptors. Neuropharmacology 38(10), 1431-1476 (1999).

    2. Schoepp, D.D. Unveiling the functions of presynaptic metabotropic glutamate receptors in the central nervous system. J. Pharmacol. Exp. Ther. 299(1), 12-20 (2001).

    3. Hawkinson, J.E., Acosta-Burruel, M., and Wood, P.L. The metabotropic glutamate receptor antagonist L-2-amino-3-phosphonopropionic acid inhibits phosphoserine phosphatase. Eur. J. Pharmacol. 307, 219-225 (1996).

    4. Otani, S., Connor, J.A., and Levy, W.B. Long-term potentiation and evidence for novel synaptic association in CA1 stratum oriens of rat hippocampus. Learn. Mem. 2(2), 101-106 (1995).

    5. Hao, L., Ding, J.H., and Hu, G. Group I mGluR ligands fail to affect 6-hydroxydopamine-induced death and glutamate release of PC12 cells. Acta Pharmacol. Sin. 24(7), 641-645 (2003).

    6. Xu, Z.H., Yang, Q., Feng, B., et al. Group I mGluR antagonist rescues the deficit of D1- induced LTP in a mouse model of fragile X syndrome. Mol. Neurodegener. 7(1), (2012).