Catalog Number: 0105
Alternate Names: DL-APV
Chemical Name: DL-2-Amino-5-phosphonopentanoic acid
Biological Activity
Potent NMDA antagonist.

D-isomer, L-isomer and Sodium Salt also available.

Technical Data
  • M.Wt:
    197.13
  • Formula:
    C5H12NO5P
  • Solubility:
    Soluble to 10 mM in water and to 100 mM in 1eq. NaOH
  • Purity:
    >98%
  • Storage:
    Store at RT
  • CAS No:
    76326-31-3
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. Actions of D and L forms of 2-amino-5-phosphonovalerate and 2-amino-4-phosphonobutyrate in the cat spinal cord.
    Davies and Watkins
    Brain Res., 1982;235:378
  2. 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
Citations:

The citations listed below are publications that use Tocris products. Selected citations for DL-AP5 include:

63 Citations: Showing 1 - 10
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  1. Electrophysiological Assessment of Serotonin and GABA Neuron Function in the Dorsal Raphe during the Third Trimester Equivalent Developmental Period in Mice(1,2,3).
    Authors: Morton Et al.
    Eneuro 2016;2
  2. Rapid dispersion of SynGAP from synaptic spines triggers AMPA receptor insertion and spine enlargement during LTP.
    Authors: Araki Et al.
    Neuron 2015;85:173
  3. Development of a neuroprotective peptide that preserves survival pathways by preventing Kidins220/ARMS calpain processing induced by excitotoxicity.
    Authors: Gamir-Morralla Et al.
    Cell Death Dis 2015;6:e1939
  4. IL-1 interacts with ethanol effects on GABAergic transmission in the mouse central amygdala.
    Authors: Bajo Et al.
    Front Pharmacol 2015;6:49
  5. GluN2B-Containing NMDA Receptors Regulate AMPA Receptor Traffic through Anchoring of the Synaptic Proteasome.
    Authors: Ferreira Et al.
    J Neurosci 2015;35:8462
  6. PAR1-activated astrocytes in the nucleus of the solitary tract stimulate adjacent neurons via NMDA receptors.
    Authors: Vance Et al.
    J Neurosci 2015;35:776
  7. Cortical Synaptic Inhibition Declines during Auditory Learning.
    Authors: Sarro Et al.
    J Neurosci 2015;35:6318
  8. Muscarinic receptors modulate dendrodendritic inhibitory synapses to sculpt glomerular output.
    Authors: Liu Et al.
    J Neurosci 2015;35:5680
  9. IGF-1 Signaling Plays an Important Role in the Formation of Three-Dimensional Laminated Neural Retina and Other Ocular Structures From Human Embryonic Stem Cells.
    Authors: Mellough Et al.
    Stem Cells 2015;33:2416
  10. Development and function of human cerebral cortex neural networks from pluripotent stem cells in vitro.
    Authors: Kirwan Et al.
    Development 2015;142:3178
  11. Rosiglitazone Suppresses In Vitro Seizures in Hippocampal Slice by Inhibiting Presynaptic Glutamate Release in a Model of Temporal Lobe Epilepsy.
    Authors: Wong Et al.
    PLoS One 2015;10:e0144806
  12. Both neurons and astrocytes exhibited tetrodotoxin-resistant metabotropic glutamate receptor-dependent spontaneous slow Ca2+ oscillations in striatum.
    Authors: Tamura Et al.
    PLoS One 2014;9:e85351
  13. The Ca2+ sensor protein swiprosin-1/EFhd2 is present in neurites and involved in kinesin-mediated transport in neurons.
    Authors: Purohit Et al.
    PLoS One 2014;9:e103976
  14. Dynamic properties of the alkaline vesicle population at hippocampal synapses.
    Authors: Röther Et al.
    PLoS One 2014;9:e102723
  15. LTD expression is independent of glutamate receptor subtype.
    Authors: Granger and Nicoll
    Front Synaptic Neurosci 2014;6:15
  16. Synapse elimination and learning rules co-regulated by MHC class I H2-Db.
    Authors: Lee Et al.
    Nature 2014;509:195
  17. Repeated binge-like ethanol drinking alters ethanol drinking patterns and depresses striatal GABAergic transmission.
    Authors: Wilcox Et al.
    Neuropsychopharmacology 2014;39:579
  18. Phasic, nonsynaptic GABA-A receptor-mediated inhibition entrains thalamocortical oscillations.
    Authors: Rovó Et al.
    J Neurosci 2014;34:7137
  19. A novel mechanism for nicotinic potentiation of glutamatergic synapses.
    Authors: Halff Et al.
    J Neurosci 2014;34:2051
  20. Moderate Alcohol Exposure during the Rat Equivalent to the Third Trimester of Human Pregnancy Alters Regulation of GABAA Receptor-Mediated Synaptic Transmission by Dopamine in the Basolateral Amygdala.
    Authors: Diaz Et al.
    Front Pediatr 2014;2:46
  21. GPR35 activation reduces Ca2+ transients and contributes to the kynurenic acid-dependent reduction of synaptic activity at CA3-CA1 synapses.
    Authors: Berlinguer-Palmini Et al.
    PLoS One 2013;8:e82180
  22. Low voltage activation of KCa1.1 current by Cav3-KCa1.1 complexes.
    Authors: Rehak Et al.
    PLoS One 2013;8:e61844
  23. Autism-related deficits via dysregulated eIF4E-dependent translational control.
    Authors: Gkogkas Et al.
    Nature 2013;493:371
  24. Extracellular signal-regulated kinase and glycogen synthase kinase 3β regulate gephyrin postsynaptic aggregation and GABAergic synaptic function in a calpain-dependent mechanism.
    Authors: Tyagarajan Et al.
    J Biol Chem 2013;288:9634
  25. Increased neuronal activity fragments the Golgi complex.
    Authors: Thayer Et al.
    Proc Natl Acad Sci U S A 2013;110:1482
  26. Chronic ethanol up-regulates the synaptic expression of the nuclear translational regulatory protein AIDA-1 in primary hippocampal neurons.
    Authors: Mulholland Et al.
    Alcohol 2012;46:569
  27. Disruption of Eaat2b, a glutamate transporter, results in abnormal motor behaviors in developing zebrafish.
    Authors: McKeown Et al.
    Dev Biol 2012;362:162
  28. Mixed electrical-chemical transmission between hippocampal mossy fibers and pyramidal cells.
    Authors: Vivar Et al.
    Eur J Neurosci 2012;35:76
  29. Activity-dependent regulation of inhibition via GAD67.
    Authors: Lau and Murthy
    J Neurosci 2012;32:8521
  30. LTP induction translocates cortactin at distant synapses in wild-type but not Fmr1 knock-out mice.
    Authors: Seese Et al.
    J Neurosci 2012;32:7403
  31. Spinal cord NMDA receptor-mediated activation of mammalian target of rapamycin is required for the development and maintenance of bone cancer-induced pain hypersensitivities in rats.
    Authors: Shih Et al.
    J Pain 2012;13:338
  32. Focal adhesion kinase regulates actin nucleation and neuronal filopodia formation during axonal growth.
    Authors: Chacón Et al.
    Development 2012;139:3200
  33. GABAergic signalling in a neurogenic niche of the turtle spinal cord.
    Authors: Reali Et al.
    J Physiol 2011;589:5633
  34. Neurogranin phosphorylation fine-tunes long-term potentiation.
    Authors: Zhong Et al.
    Eur J Neurosci 2011;33:244
  35. Functional NMDA receptors at axonal growth cones of young hippocampal neurons.
    Authors: Wang Et al.
    J Neurosci 2011;31:9289
  36. Homeostatic synaptic plasticity through changes in presynaptic calcium influx.
    Authors: Zhao Et al.
    J Neurosci 2011;31:7492
  37. Neto1 is an auxiliary subunit of native synaptic kainate receptors.
    Authors: Tang Et al.
    J Neurosci 2011;31:10009
  38. SynGAP moves out of the core of the postsynaptic density upon depolarization.
    Authors: Yang Et al.
    Neuroscience 2011;192:132
  39. M3 muscarinic acetylcholine receptor expression confers differential cholinergic modulation to neurochemically distinct hippocampal basket cell subtypes.
    Authors: Rio Et al.
    J Neurosci 2010;30:6011
  40. SAP102 is a highly mobile MAGUK in spines.
    Authors: Zheng Et al.
    J Neurosci 2010;30:4757
  41. Control of CA3 output by feedforward inhibition despite developmental changes in the excitation-inhibition balance.
    Authors: Torborg Et al.
    J Neurosci 2010;30:15628
  42. Glutamate co-release at GABA/glycinergic synapses is crucial for the refinement of an inhibitory map.
    Authors: Noh Et al.
    Nat Neurosci 2010;13:232
  43. Regulation of stargazin synaptic trafficking by C-terminal PDZ ligand phosphorylation in bidirectional synaptic plasticity.
    Authors: Stein and Chetkovich
    J Neurochem 2010;113:42
  44. A mouse model of the human Fragile X syndrome I304N mutation.
    Authors: Zang Et al.
    PLoS Genet 2009;5:e1000758
  45. Compensatory enhancement of intrinsic spiking upon NKCC1 disruption in neonatal hippocampus.
    Authors: Sipilä Et al.
    J Neurosci 2009;29:6982
  46. Co-transmission of dopamine and GABA in periglomerular cells.
    Authors: Maher and Westbrook
    J Neurophysiol 2008;99:1559
  47. Electrophysiology and pharmacology of striatal neuronal dysfunction induced by mitochondrial complex I inhibition.
    Authors: Costa Et al.
    J Neurosci 2008;28:8040
  48. NMDA receptor blockade with memantine attenuates white matter injury in a rat model of periventricular leukomalacia.
    Authors: Manning Et al.
    J Neurosci 2008;28:6670
  49. White matter vulnerability to ischemic injury increases with age because of enhanced excitotoxicity.
    Authors: Baltan Et al.
    J Neurosci 2008;28:1479
  50. Sequential changes in AMPA receptor targeting in the developing neocortical excitatory circuit.
    Authors: Brill and Huguenard
    J Neurosci 2008;28:13918
  51. Dopamine enhances fast excitatory synaptic transmission in the extended amygdala by a CRF-R1-dependent process.
    Authors: Kash Et al.
    J Neurosci 2008;28:13856
  52. Neuregulin-1 enhances depolarization-induced GABA release.
    Authors: Woo Et al.
    Neuron 2007;54:599
  53. Long-term modifications in the strength of excitatory associative inputs in the piriform cortex.
    Authors: Young and Sun
    Chem Senses 2007;32:783
  54. Metabotropic receptor-dependent long-term depression persists in the absence of protein synthesis in the mouse model of fragile X syndrome.
    Authors: Nosyreva and Huber
    J Neurophysiol 2006;95:3291
  55. Regulation of thalamocortical patterning and synaptic maturation by NeuroD2.
    Authors: Ince-Dunn Et al.
    Neuron 2006;49:683
  56. Insufficient sleep reversibly alters bidirectional synaptic plasticity and NMDA receptor function.
    Authors: Kopp Et al.
    J Neurosci 2006;26:12456
  57. GAT-3 transporters regulate inhibition in the neocortex.
    Authors: Kinney
    J Neurophysiol 2005;94:4533
  58. Glutamatergic regulation of the p70S6 kinase in primary mouse neurons.
    Authors: Lenz and Avruch
    J Biol Chem 2005;280:38121
  59. Programmed and induced phenotype of the hippocampal granule cells.
    Authors: Gómez-Lira Et al.
    J Neurosci 2005;25:6939
  60. Synchronized network activity in developing rat hippocampus involves regional hyperpolarization-activated cyclic nucleotide-gated (HCN) channel function.
    Authors: Bender Et al.
    Eur J Neurosci 2005;22:2669
  61. Metabotropic regulation of intrinsic excitability by synaptic activation of kainate receptors.
    Authors: Melyan Et al.
    J Neurosci 2004;24:4530
  62. A GDP/GTP exchange protein for the Rab3 small G protein family up-regulates a postdocking step of synaptic exocytosis in central synapses.
    Authors: Yamaguchi Et al.
    Proc Natl Acad Sci U S A 2002;99:14536
  63. Kainate receptor-mediated synaptic currents in cerebellar Golgi cells are not shaped by diffusion of glutamate.
    Authors: Bureau Et al.
    Proc Natl Acad Sci U S A 2000;97:6838
Expand to show all 63 Citations
Tocris Small Molecules
Description Application Cat# Citations Images  

D-AP5

0106 283  
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DL-AP5 Sodium salt

3693 3  
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L-AP5

0107 2  
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