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. Also available as part of the Group III mGlu Receptor Tocriset™ and Mixed mGlu Receptor Tocriset™. DL Mixture (Cat. No. 0101) and D-isomer (Cat. No. 0102) also available.
Technical Data
  • M.Wt:
  • Formula:
  • Solubility:
    Soluble to 5 mM in water and to 100 mM in 1eq. NaOH
  • Purity:
  • Storage:
    Store at RT
  • CAS No:
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.
    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

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

Showing Results 1 - 10 of 43

  1. M1 ipRGCs Influence Visual Function through Retrograde Signaling in the Retina
    Authors: Prigge Et al.
    The Journal of Neuroscience
  2. 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
  3. Glial metabotropic glutamate receptor-4 increases maturation and survival of oligodendrocytes.
    Authors: Spampinato Et al.
    Front Cell Neurosci
  4. 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
  5. The Synaptic and Morphological Basis of Orientation Selectivity in a Polyaxonal Amacrine Cell of the Rabbit Retina.
    Authors: Murphy-Baum and Taylor
    J Neurosci
  6. 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
  7. Constitutive activity of metabotropic glutamate receptor 7.
    Authors: Kammermeier
    BMC Neurosci
  8. An Amacrine Cell Circuit for Signaling Steady Illumination in the Retina.
    Authors: Jacoby Et al.
    Cell Rep
  9. The rat retina has five types of ganglion-cell photoreceptors.
    Authors: Reifler Et al.
    Exp Eye Res
  10. Examination of VLC-PUFA-deficient photoreceptor terminals.
    Authors: Bennett Et al.
    Invest Ophthalmol Vis Sci
  11. Three distinct blue-green color pathways in a mammalian retina.
    Authors: Mills Et al.
    J Neurosci
  12. Possible roles of glutamate transporter EAAT5 in mouse cone depolarizing bipolar cell light responses.
    Authors: Tse Et al.
    Vision Res
  13. Pharmacological inhibitions of glutamate transporters EAAT1 and EAAT2 compromise glutamate transport in photoreceptor to ON-bipolar cell synapses.
    Authors: Tse Et al.
    Vision Res
  14. Impaired D-serine-mediated cotransmission mediates cognitive dysfunction in epilepsy.
    Authors: Klatte Et al.
    J Neurosci
  15. Cell type-specific regulation of inhibition via cannabinoid type 1 receptors in rat neocortex.
    Authors: De-May and Ali
    J Neurophysiol
  16. Melanopsin mediates retrograde visual signaling in the retina.
    Authors: Zhang Et al.
    PLoS One
  17. Dopaminergic modulation of ganglion-cell photoreceptors in rat.
    Authors: Hook Et al.
    Eur J Neurosci
  18. The mode of retinal presynaptic inhibition switches with light intensity.
    Authors: Ichinose and Lukasiewicz
    J Neurosci
  19. Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses.
    Authors: Caiati Et al.
    Sci Rep
  20. Group III metabotropic glutamate receptors and transient receptor potential vanilloid 1 co-localize and interact on nociceptors.
    Authors: Govea Et al.
  21. Antiparkinsonian potential of targeting group III metabotropic glutamate receptor subtypes in the rodent substantia nigra pars reticulata.
    Authors: Broadstock Et al.
    Br J Pharmacol
  22. A non-canonical pathway for mammalian blue-green color vision.
    Authors: Sher and DeVries
    Nat Neurosci
  23. Depolarizing bipolar cell dysfunction due to a Trpm1 point mutation.
    Authors: Peachey Et al.
    J Neurophysiol
  24. Characterization of a truncated metabotropic glutamate receptor in a primitive metazoan, the parasitic flatworm Schistosoma mansoni.
    Authors: Taman and Ribeiro
    PLoS One
  25. Structure and function of bistratified intrinsically photosensitive retinal ganglion cells in the mouse.
    Authors: Schmidt and Kofuji
    J Comp Neurol
  26. 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
  27. RGS7 and -11 complexes accelerate the ON-bipolar cell light response.
    Authors: Zhang Et al.
    Invest Ophthalmol Vis Sci
  28. Distinct retinal deficits in a zebrafish pyruvate dehydrogenase-deficient mutant.
    Authors: Maurer Et al.
    J Neurosci
  29. Sustained glutamate receptor activation down-regulates GABAB receptors by shifting the balance from recycling to lysosomal degradation.
    Authors: Maier Et al.
    J Biol Chem
  30. 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
  31. Light-induced fos expression in intrinsically photosensitive retinal ganglion cells in melanopsin knockout (opn4) mice.
    Authors: Pickard Et al.
    PLoS One
  32. 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
  33. Corequirement of PICK1 binding and PKC phosphorylation for stable surface expression of the metabotropic glutamate receptor mGluR7.
    Authors: Suh Et al.
  34. Localization of HCN1 channels to presynaptic compartments: novel plasticity that may contribute to hippocampal maturation.
    Authors: Bender Et al.
    J Neurosci
  35. Effects of ethanol on photoreceptors and visual function in developing zebrafish.
    Authors: Matsui Et al.
    Invest Ophthalmol Vis Sci
  36. 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
  37. 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
  38. Calcium increases in retinal glial cells evoked by light-induced neuronal activity.
    Authors: Newman
    J Neurosci
  39. Melanopsin-dependent photoreception provides earliest light detection in the mammalian retina.
    Authors: Sekaran Et al.
    Curr Biol
  40. Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP.
    Authors: Mathiesen Et al.
    Br J Pharmacol
  41. Bidirectional synaptic plasticity in the cerebellum-like mammalian dorsal cochlear nucleus.
    Authors: Fujino and Oertel
    Proc Natl Acad Sci U S A
  42. Metabotropic mGlu5 receptors regulate adenosine A2A receptor signaling.
    Authors: Nishi Et al.
    Proc Natl Acad Sci U S A
  43. Neutrophil-derived glutamate regulates vascular endothelial barrier function.
    Authors: Collard Et al.
    J Biol Chem
Expand to show all
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