Catalog Number: 0103
Chemical Name: L-(+)-2-Amino-4-phosphonobutyric acid
Biological Activity
Selective group III metabotropic glutamate receptor agonist. Synaptic depressant. Agonist at the quisqualate-sensitized AP6 site in hippocampus.

Available as part of the Group III mGlu Receptor Tocriset™ and Mixed mGlu Receptor Tocriset™. DL Mixture and D-isomer also available.

Technical Data
  • M.Wt:
    183.1
  • Formula:
    C4H10NO5P
  • Solubility:
    Soluble to 5 mM in water and to 100 mM in 1eq. NaOH
  • Purity:
    >99%
  • Storage:
    Store at RT
  • CAS No:
    23052-81-5
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis. All Tocris products are intended for laboratory research use only.
Additional Information
Other Product-Specific Information:
Background References
  1. The effect of a series of ω-phosphonic-α-carboxylic amino acids on electrically evoked and amino acid induced responses in isolated spinal cord preparations.
    Evans et al.
    Br.J.Pharmacol., 1982;75:65
  2. Antagonism of the synaptic depressant actions of L-AP4 in the lateral perforant path by MAP4.
    Bushell et al.
    Neuropharmacology, 1995;34:239
  3. Molecular diversity of glutamate receptors and implications for brain functions.
    Nakanishi
    Science, 1992;258:597
  4. The agonist selectivity of a class III metabotropic glutamate receptor, human mGluR4a, is determined by the N-terminal extracellular domain.
    Tones et al.
    NeuroReport, 1995;7:117
Citations:

The citations listed below are publications that use Tocris products. Selected citations for L-AP4 include:

44 Citations: Showing 1 - 10
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  1. HTS-compatible FRET-based conformational sensors clarify membrane receptor activation.
    Authors: Scholler
    Nat Chem Biol 2017;13(4):372
  2. M1 ipRGCs Influence Visual Function through Retrograde Signaling in the Retina
    Authors: Prigge Et al.
    The Journal of Neuroscience 2016;6:7184
  3. Effects of the Concomitant Activation of ON and OFF Retinal Ganglion Cells on the Visual Thalamus: Evidence for an Enhanced Recruitment of GABAergic Cells.
    Authors: Montesano Et al.
    Front Neural Circuits 2015;9:77
  4. Glial metabotropic glutamate receptor-4 increases maturation and survival of oligodendrocytes.
    Authors: Spampinato Et al.
    Front Cell Neurosci 2015;8:462
  5. Voriconazole, an antifungal triazol that causes visual side effects, is an inhibitor of TRPM1 and TRPM3 channels.
    Authors: Xiong Et al.
    Invest Ophthalmol Vis Sci 2015;56:1367
  6. The Synaptic and Morphological Basis of Orientation Selectivity in a Polyaxonal Amacrine Cell of the Rabbit Retina.
    Authors: Murphy-Baum and Taylor
    J Neurosci 2015;35:13336
  7. Targeting channelrhodopsin-2 to ON-bipolar cells with vitreally administered AAV Restores ON and OFF visual responses in blind mice.
    Authors: Macé Et al.
    Mol Ther 2015;23:7
  8. Constitutive activity of metabotropic glutamate receptor 7.
    Authors: Kammermeier
    BMC Neurosci 2015;16:17
  9. An Amacrine Cell Circuit for Signaling Steady Illumination in the Retina.
    Authors: Jacoby Et al.
    Cell Rep 2015;13:2663
  10. The rat retina has five types of ganglion-cell photoreceptors.
    Authors: Reifler Et al.
    Exp Eye Res 2015;130:17
  11. Examination of VLC-PUFA-deficient photoreceptor terminals.
    Authors: Bennett Et al.
    Invest Ophthalmol Vis Sci 2014;55:4063
  12. Three distinct blue-green color pathways in a mammalian retina.
    Authors: Mills Et al.
    J Neurosci 2014;34:1760
  13. Possible roles of glutamate transporter EAAT5 in mouse cone depolarizing bipolar cell light responses.
    Authors: Tse Et al.
    Vision Res 2014;103:63
  14. Pharmacological inhibitions of glutamate transporters EAAT1 and EAAT2 compromise glutamate transport in photoreceptor to ON-bipolar cell synapses.
    Authors: Tse Et al.
    Vision Res 2014;103:49
  15. Impaired D-serine-mediated cotransmission mediates cognitive dysfunction in epilepsy.
    Authors: Klatte Et al.
    J Neurosci 2013;33:13066
  16. Cell type-specific regulation of inhibition via cannabinoid type 1 receptors in rat neocortex.
    Authors: De-May and Ali
    J Neurophysiol 2013;109:216
  17. Melanopsin mediates retrograde visual signaling in the retina.
    Authors: Zhang Et al.
    PLoS One 2012;7:e42647
  18. Dopaminergic modulation of ganglion-cell photoreceptors in rat.
    Authors: Hook Et al.
    Eur J Neurosci 2012;35:507
  19. The mode of retinal presynaptic inhibition switches with light intensity.
    Authors: Ichinose and Lukasiewicz
    J Neurosci 2012;32:4360
  20. Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses.
    Authors: Caiati Et al.
    Sci Rep 2012;2:285
  21. Group III metabotropic glutamate receptors and transient receptor potential vanilloid 1 co-localize and interact on nociceptors.
    Authors: Govea Et al.
    Neuroscience 2012;217:130
  22. Antiparkinsonian potential of targeting group III metabotropic glutamate receptor subtypes in the rodent substantia nigra pars reticulata.
    Authors: Broadstock Et al.
    Br J Pharmacol 2012;165:1034
  23. A non-canonical pathway for mammalian blue-green color vision.
    Authors: Sher and DeVries
    Nat Neurosci 2012;15:952
  24. Depolarizing bipolar cell dysfunction due to a Trpm1 point mutation.
    Authors: Peachey Et al.
    J Neurophysiol 2012;108:2442
  25. Characterization of a truncated metabotropic glutamate receptor in a primitive metazoan, the parasitic flatworm Schistosoma mansoni.
    Authors: Taman and Ribeiro
    PLoS One 2011;6:e27119
  26. Structure and function of bistratified intrinsically photosensitive retinal ganglion cells in the mouse.
    Authors: Schmidt and Kofuji
    J Comp Neurol 2011;519:1492
  27. A role for nyctalopin, a small leucine-rich repeat protein, in localizing the TRP melastatin 1 channel to retinal depolarizing bipolar cell dendrites.
    Authors: Pearring Et al.
    J Neurosci 2011;31:10060
  28. RGS7 and -11 complexes accelerate the ON-bipolar cell light response.
    Authors: Zhang Et al.
    Invest Ophthalmol Vis Sci 2010;51:1121
  29. Distinct retinal deficits in a zebrafish pyruvate dehydrogenase-deficient mutant.
    Authors: Maurer Et al.
    J Neurosci 2010;30:11962
  30. Sustained glutamate receptor activation down-regulates GABAB receptors by shifting the balance from recycling to lysosomal degradation.
    Authors: Maier Et al.
    J Biol Chem 2010;285:35606
  31. Retrograde intraflagellar transport by cytoplasmic dynein-2 is required for outer segment extension in vertebrate photoreceptors but not arrestin translocation.
    Authors: Krock Et al.
    Invest Ophthalmol Vis Sci 2009;50:5463
  32. Light-induced fos expression in intrinsically photosensitive retinal ganglion cells in melanopsin knockout (opn4) mice.
    Authors: Pickard Et al.
    PLoS One 2009;4:e4984
  33. GABA actions in hippocampal area CA3 during postnatal development: differential shift from depolarizing to hyperpolarizing in somatic and dendritic compartments.
    Authors: Romo-Parra Et al.
    J Neurophysiol 2008;99:1523
  34. Corequirement of PICK1 binding and PKC phosphorylation for stable surface expression of the metabotropic glutamate receptor mGluR7.
    Authors: Suh Et al.
    Neuron 2008;58:736
  35. Localization of HCN1 channels to presynaptic compartments: novel plasticity that may contribute to hippocampal maturation.
    Authors: Bender Et al.
    J Neurosci 2007;27:4697
  36. Effects of ethanol on photoreceptors and visual function in developing zebrafish.
    Authors: Matsui Et al.
    Invest Ophthalmol Vis Sci 2006;47:4589
  37. Biphenyl-indanone A, a positive allosteric modulator of the metabotropic glutamate receptor subtype 2, has antipsychotic- and anxiolytic-like effects in mice.
    Authors: Galici Et al.
    J Pharmacol Exp Ther 2006;318:173
  38. Blockade of mGluR1 receptor results in analgesia and disruption of motor and cognitive performances: effects of A-841720, a novel non-competitive mGluR1 receptor antagonist.
    Authors: El-Kouhen Et al.
    Br J Pharmacol 2006;149:761
  39. Calcium increases in retinal glial cells evoked by light-induced neuronal activity.
    Authors: Newman
    J Neurosci 2005;25:5502
  40. Melanopsin-dependent photoreception provides earliest light detection in the mammalian retina.
    Authors: Sekaran Et al.
    Curr Biol 2005;15:1099
  41. Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP.
    Authors: Mathiesen Et al.
    Br J Pharmacol 2003;138:1026
  42. Bidirectional synaptic plasticity in the cerebellum-like mammalian dorsal cochlear nucleus.
    Authors: Fujino and Oertel
    Proc Natl Acad Sci U S A 2003;100:265
  43. Metabotropic mGlu5 receptors regulate adenosine A2A receptor signaling.
    Authors: Nishi Et al.
    Proc Natl Acad Sci U S A 2003;100:1322
  44. Neutrophil-derived glutamate regulates vascular endothelial barrier function.
    Authors: Collard Et al.
    J Biol Chem 2002;277:14801
Expand to show all 44 Citations

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