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DL-AP5

Catalog #: 0105
90 Citations 1 Review Datasheet
Catalog # Availability Size / Price Qty
0105/10
0105/50
DL-AP5 | CAS No. 76326-31-3 | NMDA Receptor Antagonists
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Description: Potent and selective NMDA antagonist
Alternative Names: DL-APV

Chemical Name: DL-2-Amino-5-phosphonopentanoic acid

Purity: ≥98%

Product Details
Citations (90)
Supplemental Products
Reviews (1)
Biological Activity Technical Data Additional Information Background Product Datasheets Calculators

Biological Activity

DL-AP5 is a racemic mixture of the D- and L-isomers of AP5, a selective NMDA receptor antagonist that competes with glutamate binding and is commonly used to inhibit NMDA-dependent synaptic plasticity. D-AP5 (Cat. No. 0106) is the more active isomer and displays approximately 52-fold higher potency than the L-isomer, L-AP5 (Cat. No. 0107). In vitro D-AP5 reduces NMDA-induced depolarization of cortical neurons, with no effect on the response to L-Quisqualic acid (Cat. No. 0188) or Kainic acid (Cat. No. 0222). Following spinal injection of D-AP5, NMDA-response is rapidly reduced, with no effect seen on spontaneously active neurons.

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.
Tocris products are intended for laboratory research use only, unless stated otherwise.

Additional Information

Other Product-Specific Information:

Background References

  1. Key physiological parameters dictate triggering of activity-dependent bulk endocytosis in hippocampal synapses.
    Wenzel EM, Morton A, Ebert K, Welzel O, Kornhuber J, Cousin MA, Groemer TW
    PLoS ONE, 2012;7(6):e38188.
  2. Nutritional state-dependent ghrelin activation of vasopressin neurons via retrograde trans-neuronal-glial stimulation of excitatory GABA circuits.
    Haam J, Halmos K, Di S, Tasker J
    J Neurosci, 2014;34(18):6201-13.
  3. Neurogranin targets calmodulin and lowers the threshold for the induction of long-term potentiation.
    Zhong, Ling, Gerges, Nashaat
    PLoS ONE, 2102;7(7):e41275.
  4. Autism-related deficits via dysregulated eIF4E-dependent translational control.
    Gkogkas C, Khoutorsky A, Ran I, Rampakakis E, Nevarko T, Weatherill D, Vasuta C, Yee S, Truitt M, Dallaire P, Major F, Lasko P, Ruggero D, Nader K, Lacaille J, Sonenberg N
    Nature, 2013;493(7432):371-7.
  5. Targeted deletion of Kcne2 impairs HCN channel function in mouse thalamocortical circuits.
    Ying, Shui-Wan, Kanda, Vikram A, Hu, Zhaoyang, Purtell, Kerry, King, Elizabet, Abbott, Geoffrey, Goldstein, Peter A
    PLoS ONE, 2102;7(8):e42756.
  6. Expression of cocaine-evoked synaptic plasticity by GluN3A-containing NMDA receptors.
    Yuan T, Mameli M, O' Connor E, Dey P, Verpelli C, Sala C, Perez-Otano I, Luscher C, Bellone C
    Neuron, 2013;80(4):1025-38.
  7. Increasing the Receptor Tyrosine Kinase EphB2 Prevents Amyloid-beta-induced Depletion of Cell Surface Glutamate Receptors by a Mechanism That Requires the PDZ-binding Motif of EphB2 and Neuronal Activity.
    Miyamoto T, Kim D, Knox J, Johnson E, Mucke L
    J Biol Chem, 2016;291(4):1719-34.
  8. Importance of GluA1 subunit-containing AMPA glutamate receptors for morphine state-dependency.
    Aitta-aho T, Moykkynen TP, Panhelainen AE, Vekovischeva OY, Backstrom P, Korpi ER
    PLoS ONE, 2012;7(5):e38325.
  9. 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
  10. 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

Product Datasheets

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Citations for DL-AP5

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

90 Citations: Showing 1 - 10

  1. Multi-target action of β-alanine protects cerebellar tissue from ischemic damage.
    Authors: Kopach Et al.
    Cell Death Dis  2022;13:747
  2. TMEM16B regulates anxiety-related behavior and GABAergic neuronal signaling in the central lateral amygdala.
    Authors: Li Et al.
    Elife  2019;8
  3. Lmx1b is required at multiple stages to build expansive serotonergic axon architectures.
    Authors: Donovan Et al.
    Elife  2019;8
  4. Differences in glutamate uptake between cortical regions impact neuronal NMDA receptor activation.
    Authors: Romanos Et al.
    Commun Biol  2019;2:127
  5. Endocannabinoid Signaling Mediates Local Dendritic Coordination between Excitatory and Inhibitory Synapses.
    Authors: Hu Et al.
    Cell Rep  2019;27:666
  6. Somatostatin Interneurons Promote Neuronal Synchrony in the Neonatal Hippocampus.
    Authors: Flossmann Et al.
    Cell Rep  2019;26:3173
  7. Differential Regulation of Syngap1 Translation by FMRP Modulates eEF2 Mediated Response on NMDAR Activity.
    Authors: Paul Et al.
    Front Mol Neurosci  2019;12:97
  8. Prenatal selective serotonin reuptake inhibitor (SSRI) exposure induces working memory and social recognition deficits by disrupting inhibitory synaptic networks in male mice.
    Authors: Yu Et al.
    Mol Brain  2019;12:29
  9. Design and validation of a foldable and photovoltaic wide-field epiretinal prosthesis.
    Authors: Ferlauto Et al.
    Nat Commun  2018;9:992
  10. Pathway-specific alterations of cortico-amygdala transmission in an arthritis pain model.
    Authors: Kiritoshi and Neugebauer
    ACS Chem Neurosci  2018;9:2252
  11. Cerebrospinal Fluid-Contacting Neurons Sense pH Changes and Motion in the Hypothalamus.
    Authors: Jalalvand Et al.
    J Neurosci  2018;38:7713
  12. AKAP150 Palmitoylation Regulates Synaptic Incorporation of Ca2+-Permeable AMPA Receptors to Control LTP.
    Authors: Purkey Et al.
    Cell Rep  2018;25:974
  13. Excitotoxic inactivation of constitutive oxidative stress detoxification pathway in neurons can be rescued by PKD1.
    Authors: Pose-Utrilla Et al.
    Nat Commun  2017;8:2275
  14. Transcriptional Architecture of Synaptic Communication Delineates GABAergic Neuron Identity.
    Authors: Paul Et al.
    Cell  2017;171:522
  15. Astrocytes modulate thalamic sensory processing via mGlu2 receptor activation.
    Authors: Copeland Et al.
    Neuropharmacology  2017;121:100
  16. Loss of MeCP2 in cholinergic neurons causes part of RTT-like phenotypes via α7 receptor in hippocampus.
    Authors: Zhang Et al.
    Cell Res  2016;26:728
  17. 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
  18. Rapid dispersion of SynGAP from synaptic spines triggers AMPA receptor insertion and spine enlargement during LTP.
    Authors: Araki Et al.
    Neuron  2015;85:173
  19. 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
  20. IL-1 interacts with ethanol effects on GABAergic transmission in the mouse central amygdala.
    Authors: Bajo Et al.
    Front Pharmacol  2015;6:49
  21. GluN2B-Containing NMDA Receptors Regulate AMPA Receptor Traffic through Anchoring of the Synaptic Proteasome.
    Authors: Ferreira Et al.
    J Neurosci  2015;35:8462
  22. 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
  23. Cortical Synaptic Inhibition Declines during Auditory Learning.
    Authors: Sarro Et al.
    J Neurosci  2015;35:6318
  24. Muscarinic receptors modulate dendrodendritic inhibitory synapses to sculpt glomerular output.
    Authors: Liu Et al.
    J Neurosci  2015;35:5680
  25. 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
  26. In vivo activation of the SK channel in the spinal cord reduces the NMDA receptor antagonist dose needed to produce antinociception in an inflammatory pain model.
    Authors: Hipólito Et al.
    Pain  2015;156:849
  27. Development and function of human cerebral cortex neural networks from pluripotent stem cells in vitro.
    Authors: Kirwan Et al.
    Development  2015;142:3178
  28. 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
  29. 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
  30. 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
  31. Dynamic properties of the alkaline vesicle population at hippocampal synapses.
    Authors: Röther Et al.
    PLoS One  2014;9:e102723
  32. LTD expression is independent of glutamate receptor subtype.
    Authors: Granger and Nicoll
    Front Synaptic Neurosci  2014;6:15
  33. Synapse elimination and learning rules co-regulated by MHC class I H2-Db.
    Authors: Lee Et al.
    Nature  2014;509:195
  34. Repeated binge-like ethanol drinking alters ethanol drinking patterns and depresses striatal GABAergic transmission.
    Authors: Wilcox Et al.
    Neuropsychopharmacology  2014;39:579
  35. Nociceptin/orphanin FQ decreases glutamate transmission and blocks ethanol-induced effects in the central amygdala of naive and ethanol-dependent rats.
    Authors: Kallupi Et al.
    Neuropsychopharmacology  2014;39:1081
  36. Phasic, nonsynaptic GABA-A receptor-mediated inhibition entrains thalamocortical oscillations.
    Authors: Rovó Et al.
    J Neurosci  2014;34:7137
  37. A novel mechanism for nicotinic potentiation of glutamatergic synapses.
    Authors: Halff Et al.
    J Neurosci  2014;34:2051
  38. Moderate Alcohol Exposure during the Rat Equivalent to the Third Trimester of Human Pregnancy Alters Regulation of GABAA Receptor-Mediated Synaptic Transmission by DA in the Basolateral Amygdala.
    Authors: Diaz Et al.
    Front Pediatr  2014;2:46
  39. 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
  40. Low voltage activation of KCa1.1 current by Cav3-KCa1.1 complexes.
    Authors: Rehak Et al.
    PLoS One  2013;8:e61844
  41. Autism-related deficits via dysregulated eIF4E-dependent translational control.
    Authors: Gkogkas Et al.
    Nature  2013;493:371
  42. 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
  43. Increased neuronal activity fragments the Golgi complex.
    Authors: Thayer Et al.
    Proc Natl Acad Sci U S A  2013;110:1482
  44. Genetic inhibition of CaMKII in dorsal striatal medium spiny neurons reduces functional excitatory synapses and enhances intrinsic excitability.
    Authors: Klug Et al.
    PLoS One  2012;7:e45323
  45. Local hypocretin-1 modulates terminal DA concentration in the nucleus accumbens shell.
    Authors: Patyal Et al.
    Front Behav Neurosci  2012;6:82
  46. 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
  47. Disruption of Eaat2b, a glutamate transporter, results in abnormal motor behaviors in developing zebrafish.
    Authors: McKeown Et al.
    Dev Biol  2012;362:162
  48. Mixed electrical-chemical transmission between hippocampal mossy fibers and pyramidal cells.
    Authors: Vivar Et al.
    Eur J Neurosci  2012;35:76
  49. Activity-dependent regulation of inhibition via GAD67.
    Authors: Lau and Murthy
    J Neurosci  2012;32:8521
  50. 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
  51. Endocannabinoid-mediated long-term depression of afferent excitatory synapses in hippocampal pyramidal cells and GABAergic interneurons.
    Authors: Peterfi Et al.
    J Neurosci  2012;32:14448
  52. 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
  53. Focal adhesion kinase regulates actin nucleation and neuronal filopodia formation during axonal growth.
    Authors: Chacón Et al.
    Development  2012;139:3200
  54. Actin-dependent rapid recruitment of reluctant synaptic vesicles into a fast-releasing vesicle pool.
    Authors: Lee Et al.
    Proc Natl Acad Sci U S A  2012;109:E765
  55. Specificity and actions of an arylaspartate inhibitor of glutamate transport at the Schaffer collateral-CA1 pyramidal cell synapse.
    Authors: Sun Et al.
    PLoS One  2011;6:e23765
  56. GABAergic signalling in a neurogenic niche of the turtle spinal cord.
    Authors: Reali Et al.
    J Physiol  2011;589:5633
  57. Neurogranin phosphorylation fine-tunes long-term potentiation.
    Authors: Zhong Et al.
    Eur J Neurosci  2011;33:244
  58. Functional NMDA receptors at axonal growth cones of young hippocampal neurons.
    Authors: Wang Et al.
    J Neurosci  2011;31:9289
  59. Homeostatic synaptic plasticity through changes in presynaptic calcium influx.
    Authors: Zhao Et al.
    J Neurosci  2011;31:7492
  60. Neto1 is an auxiliary subunit of native synaptic kainate receptors.
    Authors: Tang Et al.
    J Neurosci  2011;31:10009
  61. SynGAP moves out of the core of the postsynaptic density upon depolarization.
    Authors: Yang Et al.
    Neuroscience  2011;192:132
  62. 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
  63. SAP102 is a highly mobile MAGUK in spines.
    Authors: Zheng Et al.
    J Neurosci  2010;30:4757
  64. Control of CA3 output by feedforward inhibition despite developmental changes in the excitation-inhibition balance.
    Authors: Torborg Et al.
    J Neurosci  2010;30:15628
  65. Reduction in synaptic GABA release contributes to target-selective elevation of PVN neuronal activity in rats with myocardial infarction.
    Authors: Han Et al.
    Am J Physiol Regul Integr Comp Physiol  2010;299:R129
  66. 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
  67. Regulation of stargazin synaptic trafficking by C-terminal PDZ ligand phosphorylation in bidirectional synaptic plasticity.
    Authors: Stein and Chetkovich
    J Neurochem  2010;113:42
  68. A mouse model of the human Fragile X syndrome I304N mutation.
    Authors: Zang Et al.
    PLoS Genet  2009;5:e1000758
  69. Compensatory enhancement of intrinsic spiking upon NKCC1 disruption in neonatal hippocampus.
    Authors: Sipilä Et al.
    J Neurosci  2009;29:6982
  70. Co-transmission of DA and GABA in periglomerular cells.
    Authors: Maher and Westbrook
    J Neurophysiol  2008;99:1559
  71. Electrophysiology and pharmacology of striatal neuronal dysfunction induced by mitochondrial complex I inhibition.
    Authors: Costa Et al.
    J Neurosci  2008;28:8040
  72. NMDA receptor blockade with Mem. attenuates white matter injury in a rat model of periventricular leukomalacia.
    Authors: Manning Et al.
    J Neurosci  2008;28:6670
  73. Competition between calcium-activated K+ channels determines cholinergic action on firing properties of basolateral amygdala projection neurons.
    Authors: Power and Sah
    J Neurosci  2008;28:3209
  74. White matter vulnerability to ischemic injury increases with age because of enhanced excitotoxicity.
    Authors: Baltan Et al.
    J Neurosci  2008;28:1479
  75. Sequential changes in AMPA receptor targeting in the developing neocortical excitatory circuit.
    Authors: Brill and Huguenard
    J Neurosci  2008;28:13918
  76. DA enhances fast excitatory synaptic transmission in the extended amygdala by a CRF-R1-dependent process.
    Authors: Kash Et al.
    J Neurosci  2008;28:13856
  77. Neuregulin-1 enhances depolarization-induced GABA release.
    Authors: Woo Et al.
    Neuron  2007;54:599
  78. Long-term modifications in the strength of excitatory associative inputs in the piriform cortex.
    Authors: Young and Sun
    Chem Senses  2007;32:783
  79. 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
  80. Regulation of thalamocortical patterning and synaptic maturation by NeuroD2.
    Authors: Ince-Dunn Et al.
    Neuron  2006;49:683
  81. Insufficient sleep reversibly alters bidirectional synaptic plasticity and NMDA receptor function.
    Authors: Kopp Et al.
    J Neurosci  2006;26:12456
  82. GAT-3 transporters regulate inhibition in the neocortex.
    Authors: Kinney
    J Neurophysiol  2005;94:4533
  83. Glutamatergic regulation of the p70S6 kinase in primary mouse neurons.
    Authors: Lenz and Avruch
    J Biol Chem  2005;280:38121
  84. Programmed and induced phenotype of the hippocampal granule cells.
    Authors: Gómez-Lira Et al.
    J Neurosci  2005;25:6939
  85. 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
  86. Metabotropic regulation of intrinsic excitability by synaptic activation of kainate receptors.
    Authors: Melyan Et al.
    J Neurosci  2004;24:4530
  87. Disruption of endocannabinoid release and striatal long-term depression by postsynaptic blockade of endocannabinoid membrane transport.
    Authors: Ronesi Et al.
    J Neurosci  2004;24:1673
  88. A role for ERK MAP kinase in physiologic temporal integration in hippocampal area CA1.
    Authors: Selcher Et al.
    Learn Mem  2003;10:26
  89. 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
  90. 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

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Efficient DL-AP5
By Raj Kumar on 07/25/2023
Species: Mouse

Tested the effect of DL-AP5 on treatment-induced expression of the tested protein in retinal microvessels.

Efficient DL-AP5 0105
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