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D-AP5

Catalog #: 0106
372 Citations 1 Review Datasheet
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0106/100
0106/1
D-AP5 | CAS No. 79055-68-8 | NMDA Receptor Antagonists
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Description: Potent and selective NMDA receptor antagonist; more active form of DL-AP5
Alternative Names: 2-APV,D-APV,D-2-amino-5-phosphonovalerate

Chemical Name: D-(-)-2-Amino-5-phosphonopentanoic acid

Purity: ≥99%

Product Details
Citations (372)
Supplemental Products
Reviews (1)
Biological Activity Technical Data Additional Information Background Product Datasheets Calculators

Biological Activity

D-AP5 is a selective NMDA receptor antagonist that competes with glutamate binding and is commonly used to inhibit NMDA-dependent synaptic plasticity. D-AP5 is the more active isomer of DL-AP5 (Cat. No. 0105) 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, D-AP5 results in rapid reduction of NMDA-response but no effect on spontaneously active neurons.

DL Mixture, L-isomer and sodium salt also available.

Technical Data

M.Wt:
197.13
Formula:
C5H12NO5P
Solubility:
Soluble to 100 mM in water
Purity:
≥99%
Storage:
Store at RT
CAS No:
79055-68-8

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

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Citations for D-AP5

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

372 Citations: Showing 1 - 10

  1. Voltage-gated potassium channels ensure action potential shape fidelity in distal axons.
    Authors: Sabater Et al.
    J Neurosci  2021;41:5372
  2. Axonal mechanisms mediating γ-aminobutyric acid receptor type A (GABA-A) inhibition of striatal dopamine release.
    Authors: Kramer Et al.
    ELife  2020;9
  3. Nucleus Accumbens Tac1-Expressing Neurons Mediate Stress-Induced Anhedonia-like Behavior in Mice.
    Authors: He Et al.
    Cell Rep  2020;33
  4. Functional Dissection of Basal Ganglia Inhibitory Inputs onto Substantia Nigra Dopaminergic Neurons.
    Authors: Evans Et al.
    Cell Rep  2020;32
  5. Polysynaptic inhibition between striatal cholinergic interneurons shapes their network activity patterns in a dopamine-dependent manner.
    Authors: Dorst Et al.
    Nat Comms  2020;11:5113
  6. The adhesion-GPCR BAI1 shapes dendritic arbors via Bcr-mediated RhoA activation causing late growth arrest.
    Authors: Duman Et al.
    Elife  2019;8
  7. NMDAR-Activated PP1 Dephosphorylates GluN2B to Modulate NMDAR Synaptic Content.
    Authors: Chiu Et al.
    Cell Rep  2019;28:332
  8. Pharmacological Dissection of Intrinsic Optical Signal Reveals a Functional Coupling between Synaptic Activity and Astrocytic Volume Transient.
    Authors: Woo Et al.
    Exp Neurobiol  2019;28:30
  9. Activation of Astrocytic μ-Opioid Receptor Causes Conditioned Place Preference.
    Authors: Nam Et al.
    Cell Rep  2019;28:1154
  10. Myosin VI Drives Clathrin-Mediated AMPA Receptor Endocytosis to Facilitate Cerebellar Long-Term Depression.
    Authors: Wagner Et al.
    Cell Rep  2019;28:11
  11. Routing Hippocampal Information Flow through Parvalbumin Interneuron Plasticity in Area CA2.
    Authors: Nasrallah Et al.
    Cell Rep  2019;27:86
  12. Transient, Consequential Increases in Extracellular Potassium Ions Accompany Channelrhodopsin2 Excitation.
    Authors: Octeau Et al.
    Cell Rep  2019;27:2249
  13. A Single-Cell Model for Synaptic Transmission and Plasticity in Human iPSC-Derived Neurons.
    Authors: Meijer Et al.
    Cell Rep  2019;27:2199
  14. Kibra Modulates Learning and Memory via Binding to Dendrin.
    Authors: Ji Et al.
    Cell Rep  2019;26:2064
  15. High-Frequency Microdomain Ca2+ Transients and Waves during Early Myelin Internode Remodeling.
    Authors: Battefeld Et al.
    Cell Rep  2019;26:182
  16. Homeostatic Intrinsic Plasticity Is Functionally Altered in Fmr1 KO Cortical Neurons.
    Authors: Bülow Et al.
    Cell Rep  2019;26:1378
  17. KCC2-Mediated Cl- Extrusion Modulates Spontaneous Hippocampal Network Events in Perinatal Rats and Mice.
    Authors: Spoljaric Et al.
    Cell Rep  2019;26:1073
  18. Role of intraganglionic transmission in the trigeminovascular pathway.
    Authors: Zhang Et al.
    Mol Pain  2019;15:1744806919836570
  19. Simultaneous voltage and calcium imaging and optogenetic stimulation with high sensitivity and a wide field of view.
    Authors: Nguyen Et al.
    Biomed Opt Express  2019;10:789
  20. Novel positive allosteric modulators of glutamate transport have neuroprotective properties in an in vitro excitotoxic model.
    Authors: Falcucci Et al.
    ACS Chem Neurosci  2019;10:3437
  21. How Gastrin-Releasing Peptide Opens the Spinal Gate for Itch.
    Authors: Pagani Et al.
    Neuron  2019;
  22. Activity-Dependent Downscaling of Subthreshold Synaptic Inputs during Slow-Wave-Sleep-like Activity In Vivo.
    Authors: González-Rueda Et al.
    Neuron  2018;97:1244
  23. DA neuron glutamate cotransmission evokes a delayed excitation in lateral dorsal striatal cholinergic interneurons.
    Authors: Chuhma Et al.
    Elife  2018;7
  24. A circuit from hippocampal CA2 to lateral septum disinhibits social aggression.
    Authors: Leroy Et al.
    Nature  2018;564:213
  25. The Microglial Innate Immune Receptor TREM2 Is Required for Synapse Elimination and Normal Brain Connectivity.
    Authors: Filipello Et al.
    Immunity  2018;48:979
  26. DA Cells Differentially Regulate Striatal Cholinergic Transmission across Regions through Corelease of DA and Glutamate.
    Authors: Cai and Ford
    Cell Rep  2018;25:3148
  27. Calcium Channel CaV2.3 Subunits Regulate Hepatic Glucose Production by Modulating Leptin-Induced Excitation of Arcuate Pro-opiomelanocortin Neurons.
    Authors: Smith Et al.
    Cell Rep  2018;25:278
  28. Activity-Dependent Netrin-1 Secretion Drives Synaptic Insertion of GluA1-Containing AMPA Receptors in the Hippocampus.
    Authors: Glasgow Et al.
    Cell Rep  2018;25:168
  29. CAST/ELKS Proteins Control Voltage-Gated Ca2+ Channel Density and Synaptic Release Probability at a Mammalian Central Synapse.
    Authors: Dong Et al.
    Cell Rep  2018;24:284
  30. The locus coeruleus drives disinhibition in the midline thalamus via a dopaminergic mechanism.
    Authors: Beas Et al.
    Nat Neurosci  2018;21:963
  31. Astrocytic Activation Generates De Novo Neuronal Potentiation and Memory Enhancement.
    Authors: Adamsky Et al.
    Cell  2018;174:59
  32. All-optical synaptic electrophysiology probes mechanism of ketamine-induced disinhibition.
    Authors: Fan Et al.
    Nat Methods  2018;15:823
  33. (2R,6R)-hydroxynorKA rescues chronic stress-induced depression-like behavior through its actions in the midbrain periaqueductal gray.
    Authors: Chou Et al.
    Neuropharmacology  2018;139:1
  34. Drebrin Isoforms Critically Regulate NMDAR- and mGluR-Dependent LTD Induction.
    Authors: Yasuda Et al.
    Front Cell Neurosci  2018;12:330
  35. Proximodistal Heterogeneity of Hippocampal CA3 Pyramidal Neuron Intrinsic Properties, Connectivity, and Reactivation during Memory Recall.
    Authors: Sun Et al.
    Neuron  2017;95:656
  36. Initiation of Behavioral Response to Antidepressants by Cholecystokinin Neurons of the Dentate Gyrus.
    Authors: Medrihan Et al.
    Neuron  2017;95:564
  37. Encoding of Discriminative Fear Memory by Input-Specific LTP in the Amygdala.
    Authors: Kim and Cho
    Neuron  2017;95:1129
  38. Input-Timing-Dependent Plasticity in the Hippocampal CA2 Region and Its Potential Role in Social Memory.
    Authors: Leroy Et al.
    Neuron  2017;95:1089
  39. IGF1-Dependent Synaptic Plasticity of Mitral Cells in Olfactory Memory during Social Learning.
    Authors: Liu Et al.
    Neuron  2017;95:106
  40. A Critical Role of Presynaptic Cadherin/Catenin/p140Cap Complexes in Stabilizing Spines and Functional Synapses in the Neocortex.
    Authors: Li Et al.
    Neuron  2017;94:1155
  41. Impairments of spatial memory in an Alzheimer's disease model via degeneration of hippocampal cholinergic synapses.
    Authors: Zhu Et al.
    Nat Commun  2017;8:1676
  42. Differential processing of thalamic information via distinct striatal interneuron circuits.
    Authors: Assous
    Nat Commun  2017;8:15860
  43. Subtype-specific effects of DArgic D2 receptor activation on synaptic trains in layer V pyramidal neurons in the mouse prefrontal cortex.
    Authors: Leyrer-Jackson
    Physiol Rep  2017;5(22):e13499
  44. Synaptically driven phosphorylation of ribosomal protein S6 is differentially regulated at active synapses versus dendrites and cell bodies by MAPK and PI3K/mTOR signaling pathways.
    Authors: Pirbhoy Et al.
    Learn Mem  2017;24:341
  45. DA D4 receptor activation restores CA1 LTP in hippocampal slices from aged mice.
    Authors: Guo
    Aging Cell  2017;16(6):1323
  46. Toll-like receptor 4 deficiency alters nucleus accumbens synaptic physiology and drug reward behavior.
    Authors: Kashima and Grueter
    Proc Natl Acad Sci U S A.  2017;114(3):8865
  47. Nitric Oxide Is Required for L-Type Ca(2+) Channel-Dependent Long-Term Potentiation in the Hippocampus.
    Authors: Pigott and Garthwaite
    Front Synaptic Neurosci  2016;8:17
  48. Glycinergic dysfunction in a subpopulation of dorsal horn interneurons in a rat model of neuropathic pain
    Authors: Imlach Et al.
    Scientific Reports  2016;6:37104
  49. Increased GABAB receptor signaling in a rat model for schizophrenia
    Authors: Selten Et al.
    Scientific Reports  2016;6:34240
  50. Signaling mechanism for modulation by ATP of glycine receptors on rat retinal ganglion cells.
    Authors: Zhang Et al.
    Sci Rep  2016;6:28938
  51. Endocannabinoid dynamics gate spike-timing dependent depression and potentiation.
    Authors: Cui Et al.
    Elife  2016;5:e13185
  52. A cholinergic basal forebrain feeding circuit modulates appetite suppression
    Authors: Herman Et al.
    Nature  2016;538:253
  53. Calcium-Permeable AMPA Receptors Mediate the Induction of the Protein Kinase A-Dependent Component of Long-Term Potentiation in the Hippocampus.
    Authors: Park Et al.
    J Neurosci  2016;36:622
  54. Context-Dependent Modulation of GABAAR-Mediated Tonic Currents.
    Authors: Patel Et al.
    J Neurosci  2016;36:607
  55. Hypocretin/Orexin Peptides Alter Spike Encoding by Serotonergic Dorsal Raphe Neurons through Two Distinct Mechanisms That Increase the Late Afterhyperpolarization.
    Authors: Ishibashi Et al.
    J Neurosci  2016;36:10097
  56. Activation of Muscarinic M1 Acetylcholine Receptors Induces Long-Term Potentiation in the Hippocampus.
    Authors: Dennis Et al.
    Cereb Cortex  2016;26:414
  57. Synaptic activation of ribosomal protein S6 phosphorylation occurs locally in activated dendritic domains.
    Authors: Pirbhoy Et al.
    Learn Mem  2016;23:255
  58. Diminished KCC2 confounds synapse specificity of LTP during senescence.
    Authors: Ferando Et al.
    Nat Neurosci  2016;19:1197
  59. Neuronal firing patterns outweigh circuitry oscillations in parkinsonian motor control.
    Authors: Pan Et al.
    J Clin Invest  2016;126:4516
  60. Differential modulation of repetitive firing and synchronous network activity in neocortical interneurons by inhibition of A-type K(+) channels and Ih.
    Authors: Williams and Hablitz
    Front Cell Neurosci  2015;9:89
  61. Novel agonists for serotonin 5-HT7 receptors reverse metabotropic glutamate receptor-mediated long-term depression in the hippocampus of wild-type and Fmr1 KO mice, a model of Fragile X Syndrome.
    Authors: Costa Et al.
    Front Behav Neurosci  2015;9:65
  62. NE Modulates Pyramidal Cell Synaptic Properties in the Anterior Piriform Cortex of Mice: Age-Dependent Effects of β-adrenoceptors.
    Authors: Ghosh Et al.
    Front Cell Neurosci  2015;9:450
  63. A pre-docking source for the power-law behavior of spontaneous quantal release: application to the analysis of LTP.
    Authors: Lamanna Et al.
    Front Cell Neurosci  2015;9:44
  64. Dendritic morphology, synaptic transmission, and activity of mature granule cells born following PilC-induced status epilepticus in the rat.
    Authors: Gao Et al.
    Front Cell Neurosci  2015;9:384
  65. GABAA receptor activity shapes the formation of inhibitory synapses between developing medium spiny neurons.
    Authors: Arama Et al.
    Front Cell Neurosci  2015;9:290
  66. Interaction of electrically evoked activity with intrinsic dynamics of cultured cortical networks with and without functional fast GABAergic synaptic transmission.
    Authors: Baltz and Voigt
    Front Cell Neurosci  2015;9:272
  67. Channel-mediated astrocytic glutamate modulates hippocampal synaptic plasticity by activating postsynaptic NMDA receptors.
    Authors: Park Et al.
    Mol Brain  2015;8:7
  68. Functional changes in glutamate transporters and astrocyte biophysical properties in a rodent model of focal cortical dysplasia.
    Authors: Campbell Et al.
    Front Cell Neurosci  2015;8:425
  69. Involvement of cAMP-guanine nucleotide exchange factor II in hippocampal long-term depression and behavioral flexibility.
    Authors: Lee Et al.
    Mol Brain  2015;8:38
  70. Activation of calcineurin underlies altered trafficking of α2 subunit containing GABAA receptors during prolonged epileptiform activity.
    Authors: Eckel Et al.
    Neuropharmacology  2015;88:82
  71. LRP8-Reelin-Regulated Neuronal Enhancer Signature Underlying Learning and Memory Formation.
    Authors: Telese Et al.
    Neuron  2015;86:696
  72. Calcium flux-independent NMDA receptor activity is required for Aβ oligomer-induced synaptic loss.
    Authors: Birnbaum Et al.
    Cell Death Dis  2015;6:e1791
  73. Brain ischemia downregulates the neuroprotective GDNF-Ret signaling by a calpain-dependent mechanism in cultured hippocampal neurons.
    Authors: Curcio Et al.
    Cell Death Dis  2015;6:e1645
  74. Wnt signalling tunes neurotransmitter release by directly targeting Synaptotagmin-1.
    Authors: Ciani Et al.
    Nat Commun  2015;6:8302
  75. Subventricular zone neural progenitors reverse TNF-α effects in cortical neurons.
    Authors: Morini Et al.
    Stem Cell Res Ther  2015;6:166
  76. Interactions of Human Autoantibodies with Hippocampal GABAergic Synaptic Transmission - Analyzing Antibody-Induced Effects ex vivo.
    Authors: Haselmann Et al.
    Front Neurol  2015;6:136
  77. MicroRNA miR124 is required for the expression of homeostatic synaptic plasticity.
    Authors: Hou Et al.
    Nat Commun  2015;6:10045
  78. Nitric oxide targets oligodendrocytes and promotes their morphological differentiation.
    Authors: Garthwaite Et al.
    Glia  2015;63:383
  79. GABAergic disinhibition and impaired KCC2 cotransporter activity underlie tumor-associated epilepsy.
    Authors: Campbell Et al.
    Glia  2015;63:23
  80. Histone deacetylase 3 inhibition re-establishes synaptic tagging and capture in aging through the activation of nuclear factor κ B.
    Authors: Sharma Et al.
    Sci Rep  2015;5:16616
  81. Modulation of AMPA receptor mediated current by nicotinic acetylcholine receptor in layer I neurons of rat prefrontal cortex.
    Authors: Tang Et al.
    Sci Rep  2015;5:14099
  82. Basolateral amygdala rapid glutamate release encodes an outcome-specific representation vital for reward-predictive cues to selectively invigorate reward-seeking actions.
    Authors: Malvaez Et al.
    Sci Rep  2015;5:12511
  83. Differential inhibition onto developing and mature granule cells generates high-frequency filters with variable gain.
    Authors: Pardi Et al.
    Elife  2015;4:e08764
  84. Retroactive modulation of spike timing-dependent plasticity by DA.
    Authors: Brzosko Et al.
    Elife  2015;4
  85. AMPA receptor mediated synaptic excitation drives state-dependent bursting in Purkinje neurons of zebrafish larvae.
    Authors: Sengupta and Thirumalai
    Elife  2015;4
  86. Neuron-glia signaling in developing retina mediated by neurotransmitter spillover.
    Authors: Rosa Et al.
    Elife  2015;4
  87. Pronociceptive and Antinociceptive Effects of Bupren. in the Spinal Cord Dorsal Horn Cover a Dose Range of Four Orders of Magnitude.
    Authors: Gerhold Et al.
    J Neurosci  2015;35:9580
  88. An Asymmetric Increase in Inhibitory Synapse Number Underlies the Development of a Direction Selective Circuit in the Retina.
    Authors: Morrie and Feller
    J Neurosci  2015;35:9281
  89. Disruption of Fgf13 causes synaptic excitatory-inhibitory imbalance and genetic epilepsy and febrile seizures plus.
    Authors: Puranam Et al.
    J Neurosci  2015;35:8866
  90. Developmental changes in synaptic distribution in arcuate nucleus neurons.
    Authors: Baquero Et al.
    J Neurosci  2015;35:8558
  91. Different patterns of electrical activity lead to long-term potentiation by activating different intracellular pathways.
    Authors: Zhu Et al.
    J Neurosci  2015;35:621
  92. Abnormal excitability and episodic low-frequency oscillations in the cerebral cortex of the tottering mouse.
    Authors: Cramer Et al.
    J Neurosci  2015;35:5664
  93. BDNF interacts with endocannabinoids to regulate cocaine-induced synaptic plasticity in mouse midbrain DA neurons.
    Authors: Zhong Et al.
    J Neurosci  2015;35:4469
  94. Absence of plateau potentials in dLGN cells leads to a breakdown in retinogeniculate refinement.
    Authors: Dilger Et al.
    J Neurosci  2015;35:3652
  95. Miro1 Regulates Activity-Driven Positioning of Mitochondria within Astrocytic Processes Apposed to Synapses to Regulate Intracellular Calcium Signaling.
    Authors: Stephen Et al.
    J Neurosci  2015;35:15996
  96. Loss of Local Astrocyte Support Disrupts Action Potential Propagation and Glutamate Release Synchrony from Unmyelinated Hippocampal Axon Terminals In Vitro.
    Authors: Sobieski Et al.
    J Neurosci  2015;35:11105
  97. Afterhyperpolarization (AHP) regulates the frequency and timing of action potentials in the mitral cells of the olfactory bulb: role of olfactory experience.
    Authors: Duménieu Et al.
    Physiol Rep  2015;3
  98. Synapse-specific compartmentalization of signaling cascades for LTP induction in CA3 interneurons.
    Authors: Galván Et al.
    Neuroscience  2015;290:332
  99. Asynchronous GABA Release Is a Key Determinant of Tonic Inhibition and Controls Neuronal Excitability: A Study in the Synapsin II-/- Mouse.
    Authors: Medrihan Et al.
    Cereb Cortex  2015;25:3356
  100. Morphological and physiological evidence of a synaptic connection between the lateral parabrachial nucleus and neurons in the A7 catecholamine cell group in rats.
    Authors: Liu Et al.
    J Biomed Sci  2015;22:79
  101. Tau reduction prevents Aβ-induced axonal transport deficits by blocking activation of GSK3β.
    Authors: Vossel Et al.
    J Cell Biol  2015;209:419
  102. Neuraminidase inhibition primes short-term depression and suppresses long-term potentiation of synaptic transmission in the rat hippocampus.
    Authors: Savotchenko Et al.
    Neural Plast  2015;2015:908190
  103. Selective Effects of PDE10A Inhibitors on Striatopallidal Neurons Require Phosphatase Inhibition by DARPP-32(1,2,3).
    Authors: Polito Et al.
    Eneuro  2015;2
  104. Visual recognition memory, manifested as long-term habituation, requires synaptic plasticity in V1.
    Authors: Cooke Et al.
    Nat Neurosci  2015;18:262
  105. Functional α7 nicotinic receptors are expressed on immature granule cells of the postnatal dentate gyrus.
    Authors: John Et al.
    Brain Res  2015;1601:15
  106. The Posterodorsal Medial Amygdala Regulates the Timing of Puberty Onset in Female Rats.
    Authors: Li Et al.
    Endocrinology  2015;156:3725
  107. The rat retina has five types of ganglion-cell photoreceptors.
    Authors: Reifler Et al.
    Exp Eye Res  2015;130:17
  108. Functional cortical neurons and astrocytes from human pluripotent stem cells in 3D culture.
    Authors: Pasca Et al.
    Nat Methods  2015;12:671
  109. PacT. induces acute pain via directly activating toll like receptor 4.
    Authors: Yan Et al.
    Mol Pain  2015;11:10
  110. Intrinsic excitability varies by sex in prepubertal striatal medium spiny neurons.
    Authors: Dorris Et al.
    J Neurophysiol  2015;113:720
  111. Structural elements that underlie Doc2β function during asynchronous synaptic transmission.
    Authors: Xue Et al.
    Proc Natl Acad Sci U S A  2015;112:E4316
  112. Tectal microcircuit generating visual selection commands on gaze-controlling neurons.
    Authors: Kardamakis Et al.
    Proc Natl Acad Sci U S A  2015;112:E1956
  113. ATRX tolerates activity-dependent histone H3 methyl/phos switching to maintain repetitive element silencing in neurons.
    Authors: Noh Et al.
    Proc Natl Acad Sci U S A  2015;112:6820
  114. Regulation of AMPA receptor phosphorylation by the neuropeptide PACAP38.
    Authors: Toda and Huganir
    Proc Natl Acad Sci U S A  2015;112:6712
  115. Giant ankyrin-G stabilizes somatodendritic GABAergic synapses through opposing endocytosis of GABAA receptors.
    Authors: Tseng Et al.
    Proc Natl Acad Sci U S A  2015;112:1214
  116. Apamin Boosting of Synaptic Potentials in CaV2.3 R-Type Ca2+ Channel Null Mice.
    Authors: Wang Et al.
    PLoS One  2015;10:e0139332
  117. Chloride Accumulators NKCC1 and AE2 in Mouse GnRH Neurons: Implications for GABAA Mediated Excitation.
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NMDA antagonist
By Anonymous on 07/17/2017

NMDA antagonist

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