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L-AP4 | CAS No. 23052-81-5 | Group III mGluR Agonists
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Description: Selective group III mGlu agonist

Chemical Name: L-(+)-2-Amino-4-phosphonobutyric acid

Purity: ≥99%

Product Details
Citations (56)
Supplemental Products

Biological Activity

L-AP4 is a selective group III metabotropic glutamate receptor agonist that acts at mGlu4, mGlu8, mGlu6 and mGlu7 receptors (EC50 values = 0.1-0.13 μM, 0.29 μM, 1.0-2.4 μM and 249-337 μM, respectively). L-AP4 is a synaptic depressant and inhibits excitatory post-synaptic currents. L-AP4 is also an agonist at the quisqualate-sensitized AP6 site in hippocampus.

DL Mixture and D-isomer also available.

Technical Data

Soluble to 5 mM in water and to 100 mM in 1eq. NaOH
Store at RT

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.

Additional Information

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Citations for L-AP4

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

56 Citations: Showing 1 - 10

  1. Inhibition, but not excitation, recovers from partial cone loss with greater spatiotemporal integration, synapse density, and frequency.
    Authors: Lee Et al.
    Cell Rep.  2022;38:110317
  2. Voltage-gated potassium channels ensure action potential shape fidelity in distal axons.
    Authors: Sabater Et al.
    J Neurosci  2021;41:5372
  3. Oxytocin shapes spontaneous activity patterns in the developing visual cortex by activating somatostatin interneurons.
    Authors: Maldonado Et al.
    Curr Biol  2021;31:322
  4. Essential Roles of Tbr1 in the Formation and Maintenance of the Orientation-Selective J-RGCs and a Group of OFF-Sustained RGCs in Mouse.
    Authors: Kiyama Et al.
    Cell Rep  2019;27:900
  5. Neural Mechanisms Mediating Motion Sensitivity in Parasol Ganglion Cells of the Primate Retina.
    Authors: Manookin Et al.
    Neuron  2018;97:1327
  6. A group I metabotropic glutamate receptor controls synaptic gain between rods and rod bipolar cells in the mouse retina.
    Authors: Hellmer Et al.
    Physiol Rep  2018;6:e13885
  7. The Development of Mid-Wavelength Photoresponsivity in the Mouse Retina.
    Authors: Bonezzi Et al.
    Curr Eye Res  2018;43:666
  8. A New Promoter Allows Optogenetic Vision Restoration with Enhanced Sensitivity in Macaque Retina.
    Authors: Chaffiol Et al.
    Mol Ther  2017;25:2546
  9. HTS-compatible FRET-based conformational sensors clarify membrane receptor activation.
    Authors: Scholler
    Nat Chem Biol  2017;13(4):372
  10. M1 ipRGCs Influence Visual Function through Retrograde Signaling in the Retina
    Authors: Prigge Et al.
    The Journal of Neuroscience  2016;6:7184
  11. 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
  12. Glial metabotropic glutamate receptor-4 increases maturation and survival of oligodendrocytes.
    Authors: Spampinato Et al.
    Front Cell Neurosci  2015;8:462
  13. 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
  14. 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
  15. 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
  16. Constitutive activity of metabotropic glutamate receptor 7.
    Authors: Kammermeier
    BMC Neurosci  2015;16:17
  17. An Amacrine Cell Circuit for Signaling Steady Illumination in the Retina.
    Authors: Jacoby Et al.
    Cell Rep  2015;13:2663
  18. The rat retina has five types of ganglion-cell photoreceptors.
    Authors: Reifler Et al.
    Exp Eye Res  2015;130:17
  19. Examination of VLC-PUFA-deficient photoreceptor terminals.
    Authors: Bennett Et al.
    Invest Ophthalmol Vis Sci  2014;55:4063
  20. Three distinct blue-green color pathways in a mammalian retina.
    Authors: Mills Et al.
    J Neurosci  2014;34:1760
  21. Possible roles of glutamate transporter EAAT5 in mouse cone depolarizing bipolar cell light responses.
    Authors: Tse Et al.
    Vision Res  2014;103:63
  22. 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
  23. PrPC controls via protein kinase A the direction of synaptic plasticity in the immature hippocampus.
    Authors: Caiati Et al.
    J Neurosci  2013;33:2973
  24. Impaired D-serine-mediated cotransmission mediates cognitive dysfunction in epilepsy.
    Authors: Klatte Et al.
    J Neurosci  2013;33:13066
  25. Cell type-specific regulation of inhibition via cannabinoid type 1 receptors in rat neocortex.
    Authors: De-May and Ali
    J Neurophysiol  2013;109:216
  26. Melanopsin mediates retrograde visual signaling in the retina.
    Authors: Zhang Et al.
    PLoS One  2012;7:e42647
  27. DArgic modulation of ganglion-cell photoreceptors in rat.
    Authors: Hook Et al.
    Eur J Neurosci  2012;35:507
  28. The mode of retinal presynaptic inhibition switches with light intensity.
    Authors: Ichinose and Lukasiewicz
    J Neurosci  2012;32:4360
  29. Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses.
    Authors: Caiati Et al.
    Sci Rep  2012;2:285
  30. 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
  31. 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
  32. A non-canonical pathway for mammalian blue-green color vision.
    Authors: Sher and DeVries
    Nat Neurosci  2012;15:952
  33. Depolarizing bipolar cell dysfunction due to a Trpm1 point mutation.
    Authors: Peachey Et al.
    J Neurophysiol  2012;108:2442
  34. 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
  35. Structure and function of bistratified intrinsically photosensitive retinal ganglion cells in the mouse.
    Authors: Schmidt and Kofuji
    J Comp Neurol  2011;519:1492
  36. 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
  37. RGS7 and -11 complexes accelerate the ON-bipolar cell light response.
    Authors: Zhang Et al.
    Invest Ophthalmol Vis Sci  2010;51:1121
  38. Distinct retinal deficits in a zebrafish pyruvate dehydrogenase-deficient mutant.
    Authors: Maurer Et al.
    J Neurosci  2010;30:11962
  39. 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
  40. 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
  41. Light-induced fos expression in intrinsically photosensitive retinal ganglion cells in melanopsin knockout (opn4) mice.
    Authors: Pickard Et al.
    PLoS One  2009;4:e4984
  42. 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
  43. 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
  44. Localization of HCN1 channels to presynaptic compartments: novel plasticity that may contribute to hippocampal maturation.
    Authors: Bender Et al.
    J Neurosci  2007;27:4697
  45. Effects of ethanol on photoreceptors and visual function in developing zebrafish.
    Authors: Matsui Et al.
    Invest Ophthalmol Vis Sci  2006;47:4589
  46. 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
  47. Activation of group III metabotropic glutamate receptors attenuates rotenone toxicity on DArgic neurons through a microtubule-dependent mechanism.
    Authors: Jiang Et al.
    J Neurosci  2006;26:4318
  48. Activation of kainate receptors sensitizes oligodendrocytes to complement attack.
    Authors: Alberdi Et al.
    J Neurosci  2006;26:3220
  49. Umami responses in mouse taste cells indicate more than one receptor.
    Authors: Maruyama Et al.
    J Neurosci  2006;26:2227
  50. 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
  51. Calcium increases in retinal glial cells evoked by light-induced neuronal activity.
    Authors: Newman
    J Neurosci  2005;25:5502
  52. Melanopsin-dependent photoreception provides earliest light detection in the mammalian retina.
    Authors: Sekaran Et al.
    Curr Biol  2005;15:1099
  53. 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
  54. 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
  55. Metabotropic mGlu5 receptors regulate adenosine A2A receptor signaling.
    Authors: Nishi Et al.
    Proc Natl Acad Sci U S A  2003;100:1322
  56. Neutrophil-derived glutamate regulates vascular endothelial barrier function.
    Authors: Collard Et al.
    J Biol Chem  2002;277:14801


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