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Submit ReviewDL-AP5
Description: Potent and selective NMDA antagonist
Alternative Names: DL-APV
Chemical Name: DL-2-Amino-5-phosphonopentanoic acid
Purity: ≥98% (HPLC)
Biological Activity for DL-AP5
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 for DL-AP5
| M. Wt | 197.13 |
| Formula | C5H12NO5P |
| Storage | Store at RT |
| Purity | ≥98% (HPLC) |
| CAS Number | 76326-31-3 |
| PubChem ID | 1216 |
| InChI Key | VOROEQBFPPIACJ-UHFFFAOYSA-N |
| Smiles | NC(C(O)=O)CCCP(O)(O)=O |
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.
Solubility Data for DL-AP5
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 1.97 | 10 | |
| 1eq. NaOH | 19.71 | 100 |
Preparing Stock Solutions for DL-AP5
The following data is based on the product molecular weight 197.13. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 5.07 mL | 25.36 mL | 50.73 mL |
| 5 mM | 1.01 mL | 5.07 mL | 10.15 mL |
| 10 mM | 0.51 mL | 2.54 mL | 5.07 mL |
| 50 mM | 0.1 mL | 0.51 mL | 1.01 mL |
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Product Datasheets for DL-AP5
References for DL-AP5
References are publications that support the biological activity of the product.
Davies and Watkins (1982) Actions of D and L forms of 2-amino-5-phosphonovalerate and 2-amino-4-phosphonobutyrate in the cat spinal cord. Brain Res. 235 378 PMID: 6145492
Evans et al (1982) 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. Br.J.Pharmacol. 75 65 PMID: 7042024
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Keywords: DL-AP5, DL-AP5 supplier, Potent, selective, NMDA, antagonists, Glutamate, Receptors, N-Methyl-D-Aspartate, iGlu, Ionotropic, DL-APV, DLAPV, DL_APV, 0105, Tocris Bioscience
90 Citations for DL-AP5
Citations are publications that use Tocris products. Selected citations for DL-AP5 include:
Pose-Utrilla et al (2017) Excitotoxic inactivation of constitutive oxidative stress detoxification pathway in neurons can be rescued by PKD1. Nat Commun 8 2275 PMID: 29273751
Wilcox et al (2014) Repeated binge-like ethanol drinking alters ethanol drinking patterns and depresses striatal GABAergic transmission. Neuropsychopharmacology 39 579 PMID: 23995582
Röther et al (2014) Dynamic properties of the alkaline vesicle population at hippocampal synapses. PLoS One 9 e102723 PMID: 25079223
Halff et al (2014) A novel mechanism for nicotinic potentiation of glutamatergic synapses. J Neurosci 34 2051 PMID: 24501347
Tamura et al (2014) Both neurons and astrocytes exhibited tetrodotoxin-resistant metabotropic glutamate receptor-dependent spontaneous slow Ca2+ oscillations in striatum. PLoS One 9 e85351 PMID: 24454845
Rehak et al (2013) Low voltage activation of KCa1.1 current by Cav3-KCa1.1 complexes. PLoS One 8 e61844 PMID: 23626738
Tyagarajan et al (2013) Extracellular signal-regulated kinase and glycogen synthase kinase 3β regulate gephyrin postsynaptic aggregation and GABAergic synaptic function in a calpain-dependent mechanism. J Biol Chem 288 9634 PMID: 23408424
Thayer et al (2013) Increased neuronal activity fragments the Golgi complex. Proc Natl Acad Sci U S A 110 1482 PMID: 23297202
Berlinguer-Palmini et al (2013) GPR35 activation reduces Ca2+ transients and contributes to the kynurenic acid-dependent reduction of synaptic activity at CA3-CA1 synapses. PLoS One 8 e82180 PMID: 24312407
Zang et al (2009) A mouse model of the human Fragile X syndrome I304N mutation. PLoS Genet 5 e1000758 PMID: 20011099
Flossmann et al (2019) Somatostatin Interneurons Promote Neuronal Synchrony in the Neonatal Hippocampus. Cell Rep 26 3173 PMID: 30893591
Sun et al (2011) Specificity and actions of an arylaspartate inhibitor of glutamate transport at the Schaffer collateral-CA1 pyramidal cell synapse. PLoS One 6 e23765 PMID: 21887314
Donovan et al (2019) Lmx1b is required at multiple stages to build expansive serotonergic axon architectures. Elife 8 PMID: 31355748
Hipólito et al (2015) 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. Pain 156 849 PMID: 25734988
Wong et al (2015) Rosiglitazone Suppresses In Vitro Seizures in Hippocampal Slice by Inhibiting Presynaptic Glutamate Release in a Model of Temporal Lobe Epilepsy. PLoS One 10 e0144806 PMID: 26659605
Araki et al (2015) Rapid dispersion of SynGAP from synaptic spines triggers AMPA receptor insertion and spine enlargement during LTP. Neuron 85 173 PMID: 25569349
Sarro et al (2015) Cortical Synaptic Inhibition Declines during Auditory Learning. J Neurosci 35 6318 PMID: 25904785
Bajo et al (2015) IL-1 interacts with ethanol effects on GABAergic transmission in the mouse central amygdala. Front Pharmacol 6 49 PMID: 25852553
Liu et al (2015) Muscarinic receptors modulate dendrodendritic inhibitory synapses to sculpt glomerular output. J Neurosci 35 5680 PMID: 25855181
Vance et al (2015) PAR1-activated astrocytes in the nucleus of the solitary tract stimulate adjacent neurons via NMDA receptors. J Neurosci 35 776 PMID: 25589770
Ferreira et al (2015) GluN2B-Containing NMDA Receptors Regulate AMPA Receptor Traffic through Anchoring of the Synaptic Proteasome. J Neurosci 35 8462 PMID: 26041915
Mellough et al (2015) 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. Stem Cells 33 2416 PMID: 25827910
Gamir-Morralla et al (2015) Development of a neuroprotective peptide that preserves survival pathways by preventing Kidins220/ARMS calpain processing induced by excitotoxicity. Cell Death Dis 6 e1939 PMID: 26492372
Kirwan et al (2015) Development and function of human cerebral cortex neural networks from pluripotent stem cells in vitro. Development 142 3178 PMID: 26395144
Purohit et al (2014) The Ca2+ sensor protein swiprosin-1/EFhd2 is present in neurites and involved in kinesin-mediated transport in neurons. PLoS One 9 e103976 PMID: 25133820
Diaz et al (2014) 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. Front Pediatr 2 46 PMID: 24904907
Lee et al (2014) Synapse elimination and learning rules co-regulated by MHC class I H2-Db. Nature 509 195 PMID: 24695230
Rovó et al (2014) Phasic, nonsynaptic GABA-A receptor-mediated inhibition entrains thalamocortical oscillations. J Neurosci 34 7137 PMID: 24849349
Patyal et al (2012) Local hypocretin-1 modulates terminal DA concentration in the nucleus accumbens shell. Front Behav Neurosci 6 82 PMID: 23226119
Peterfi et al (2012) Endocannabinoid-mediated long-term depression of afferent excitatory synapses in hippocampal pyramidal cells and GABAergic interneurons. J Neurosci 32 14448 PMID: 23055515
Lee et al (2012) Actin-dependent rapid recruitment of reluctant synaptic vesicles into a fast-releasing vesicle pool. Proc Natl Acad Sci U S A 109 E765 PMID: 22393020
Klug et al (2012) Genetic inhibition of CaMKII in dorsal striatal medium spiny neurons reduces functional excitatory synapses and enhances intrinsic excitability. PLoS One 7 e45323 PMID: 23028932
Maher and Westbrook (2008) Co-transmission of DA and GABA in periglomerular cells. J Neurophysiol 99 1559 PMID: 18216231
Brill and Huguenard (2008) Sequential changes in AMPA receptor targeting in the developing neocortical excitatory circuit. J Neurosci 28 13918 PMID: 19091980
Power and Sah (2008) Competition between calcium-activated K+ channels determines cholinergic action on firing properties of basolateral amygdala projection neurons. J Neurosci 28 3209 PMID: 18354024
Hu et al (2019) Endocannabinoid Signaling Mediates Local Dendritic Coordination between Excitatory and Inhibitory Synapses. Cell Rep 27 666 PMID: 30995465
Paul et al (2019) Differential Regulation of Syngap1 Translation by FMRP Modulates eEF2 Mediated Response on NMDAR Activity. Front Mol Neurosci 12 97 PMID: 31143100
Romanos et al (2019) Differences in glutamate uptake between cortical regions impact neuronal NMDA receptor activation. Commun Biol 2 127 PMID: 30963115
Yu et al (2019) Prenatal selective serotonin reuptake inhibitor (SSRI) exposure induces working memory and social recognition deficits by disrupting inhibitory synaptic networks in male mice. Mol Brain 12 29 PMID: 30935412
Li et al (2019) TMEM16B regulates anxiety-related behavior and GABAergic neuronal signaling in the central lateral amygdala. Elife 8 PMID: 31482844
Copeland et al (2017) Astrocytes modulate thalamic sensory processing via mGlu2 receptor activation. Neuropharmacology 121 100 PMID: 28416443
Lau and Murthy (2012) Activity-dependent regulation of inhibition via GAD67. J Neurosci 32 8521 PMID: 22723692
Han et al (2010) Reduction in synaptic GABA release contributes to target-selective elevation of PVN neuronal activity in rats with myocardial infarction. Am J Physiol Regul Integr Comp Physiol 299 R129 PMID: 20164200
Jalalvand et al (2018) Cerebrospinal Fluid-Contacting Neurons Sense pH Changes and Motion in the Hypothalamus. J Neurosci 38 7713 PMID: 30037834
Zhang et al (2016) Loss of MeCP2 in cholinergic neurons causes part of RTT-like phenotypes via α7 receptor in hippocampus. Cell Res 26 728 PMID: 27103432
Kallupi et al (2014) Nociceptin/orphanin FQ decreases glutamate transmission and blocks ethanol-induced effects in the central amygdala of naive and ethanol-dependent rats. Neuropsychopharmacology 39 1081 PMID: 24169802
Shih et al (2012) 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. J Pain 13 338 PMID: 22341316
Seese et al (2012) LTP induction translocates cortactin at distant synapses in wild-type but not Fmr1 knock-out mice. J Neurosci 32 7403 PMID: 22623686
Vivar et al (2012) Mixed electrical-chemical transmission between hippocampal mossy fibers and pyramidal cells. Eur J Neurosci 35 76 PMID: 22151275
Zheng et al (2010) SAP102 is a highly mobile MAGUK in spines. J Neurosci 30 4757 PMID: 20357126
Torborg et al (2010) Control of CA3 output by feedforward inhibition despite developmental changes in the excitation-inhibition balance. J Neurosci 30 15628 PMID: 21084618
Stein and Chetkovich (2010) Regulation of stargazin synaptic trafficking by C-terminal PDZ ligand phosphorylation in bidirectional synaptic plasticity. J Neurochem 113 42 PMID: 19968761
Kopach et al (2022) Multi-target action of β-alanine protects cerebellar tissue from ischemic damage. Cell Death Dis 13 747 PMID: 36038575
Kiritoshi and Neugebauer (2018) Pathway-specific alterations of cortico-amygdala transmission in an arthritis pain model. ACS Chem Neurosci 9 2252 PMID: 29630339
Granger and Nicoll (2014) LTD expression is independent of glutamate receptor subtype. Front Synaptic Neurosci 6 15 PMID: 25071549
Gkogkas et al (2013) Autism-related deficits via dysregulated eIF4E-dependent translational control. Nature 493 371 PMID: 23172145
Mulholland et al (2012) Chronic ethanol up-regulates the synaptic expression of the nuclear translational regulatory protein AIDA-1 in primary hippocampal neurons. Alcohol 46 569 PMID: 22703994
McKeown et al (2012) Disruption of Eaat2b, a glutamate transporter, results in abnormal motor behaviors in developing zebrafish. Dev Biol 362 162 PMID: 22094018
Chacón et al (2012) Focal adhesion kinase regulates actin nucleation and neuronal filopodia formation during axonal growth. Development 139 3200 PMID: 22872087
Zhao et al (2011) Homeostatic synaptic plasticity through changes in presynaptic calcium influx. J Neurosci 31 7492 PMID: 21593333
Tang et al (2011) Neto1 is an auxiliary subunit of native synaptic kainate receptors. J Neurosci 31 10009 PMID: 21734292
Zhong et al (2011) Neurogranin phosphorylation fine-tunes long-term potentiation. Eur J Neurosci 33 244 PMID: 21198977
Wang et al (2011) Functional NMDA receptors at axonal growth cones of young hippocampal neurons. J Neurosci 31 9289 PMID: 21697378
Rio et al (2010) M3 muscarinic acetylcholine receptor expression confers differential cholinergic modulation to neurochemically distinct hippocampal basket cell subtypes. J Neurosci 30 6011 PMID: 20427660
Noh et al (2010) Glutamate co-release at GABA/glycinergic synapses is crucial for the refinement of an inhibitory map. Nat Neurosci 13 232 PMID: 20081852
Ferlauto et al (2018) Design and validation of a foldable and photovoltaic wide-field epiretinal prosthesis. Nat Commun 9 992 PMID: 29520006
Purkey et al (2018) AKAP150 Palmitoylation Regulates Synaptic Incorporation of Ca2+-Permeable AMPA Receptors to Control LTP. Cell Rep 25 974 PMID: 30355502
Paul et al (2017) Transcriptional Architecture of Synaptic Communication Delineates GABAergic Neuron Identity. Cell 171 522 PMID: 28942923
Morton et al (2016) Electrophysiological Assessment of Serotonin and GABA Neuron Function in the Dorsal Raphe during the Third Trimester Equivalent Developmental Period in Mice(1,2,3). Eneuro 2 PMID: 26730407
Reali et al (2011) GABAergic signalling in a neurogenic niche of the turtle spinal cord. J Physiol 589 5633 PMID: 21911613
Yang et al (2011) SynGAP moves out of the core of the postsynaptic density upon depolarization. Neuroscience 192 132 PMID: 21736925
Woo et al (2007) Neuregulin-1 enhances depolarization-induced GABA release. Neuron 54 599 PMID: 17521572
Young and Sun (2007) Long-term modifications in the strength of excitatory associative inputs in the piriform cortex. Chem Senses 32 783 PMID: 17634388
Bureau et al (2000) Kainate receptor-mediated synaptic currents in cerebellar Golgi cells are not shaped by diffusion of glutamate. Proc Natl Acad Sci U S A 97 6838 PMID: 10841579
Ronesi et al (2004) Disruption of endocannabinoid release and striatal long-term depression by postsynaptic blockade of endocannabinoid membrane transport. J Neurosci 24 1673 PMID: 14973237
Selcher et al (2003) A role for ERK MAP kinase in physiologic temporal integration in hippocampal area CA1. Learn Mem 10 26 PMID: 12551961
Yamaguchi et al (2002) A GDP/GTP exchange protein for the Rab3 small G protein family up-regulates a postdocking step of synaptic exocytosis in central synapses. Proc Natl Acad Sci U S A 99 14536 PMID: 12388783
Gómez-Lira et al (2005) Programmed and induced phenotype of the hippocampal granule cells. J Neurosci 25 6939 PMID: 16049169
Bender et al (2005) Synchronized network activity in developing rat hippocampus involves regional hyperpolarization-activated cyclic nucleotide-gated (HCN) channel function. Eur J Neurosci 22 2669 PMID: 16307610
Melyan et al (2004) Metabotropic regulation of intrinsic excitability by synaptic activation of kainate receptors. J Neurosci 24 4530 PMID: 15140923
Sipilä et al (2009) Compensatory enhancement of intrinsic spiking upon NKCC1 disruption in neonatal hippocampus. J Neurosci 29 6982 PMID: 19474325
Manning et al (2008) NMDA receptor blockade with Mem. attenuates white matter injury in a rat model of periventricular leukomalacia. J Neurosci 28 6670 PMID: 18579741
Kash et al (2008) DA enhances fast excitatory synaptic transmission in the extended amygdala by a CRF-R1-dependent process. J Neurosci 28 13856 PMID: 19091975
Baltan et al (2008) White matter vulnerability to ischemic injury increases with age because of enhanced excitotoxicity. J Neurosci 28 1479 PMID: 18256269
Costa et al (2008) Electrophysiology and pharmacology of striatal neuronal dysfunction induced by mitochondrial complex I inhibition. J Neurosci 28 8040 PMID: 18685029
Ince-Dunn et al (2006) Regulation of thalamocortical patterning and synaptic maturation by NeuroD2. Neuron 49 683 PMID: 16504944
Kopp et al (2006) Insufficient sleep reversibly alters bidirectional synaptic plasticity and NMDA receptor function. J Neurosci 26 12456 PMID: 17135407
Nosyreva and Huber (2006) Metabotropic receptor-dependent long-term depression persists in the absence of protein synthesis in the mouse model of fragile X syndrome. J Neurophysiol 95 3291 PMID: 16452252
Kinney (2005) GAT-3 transporters regulate inhibition in the neocortex. J Neurophysiol 94 4533 PMID: 16135550
Lenz and Avruch (2005) Glutamatergic regulation of the p70S6 kinase in primary mouse neurons. J Biol Chem 280 38121 PMID: 16183639
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Reviews for DL-AP5
Average Rating: 5 (Based on 3 Reviews.)
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AP5 action at NMDARs.
By
Anonymous on 06/21/2023
Assay Type: Ex Vivo
Species: Mouse
Cell Line/Tissue: Hypothalamus
AP5 was in use as a control pharmacological intervention to prove NMDAR-related nature of the registered whole-cell electrophysiological response. 20 microM/l AP5 supressed the response immediately. Red trace: whole-cell response without AP5; black trace: after AP5 application.
Needs stirring to be diluted.
NMDA antagonist.
By
Anonymous on 10/02/2018
Assay Type: Ex Vivo
Species: Mouse
Blocks NMDA currents as expected
blocks within 5 minutes.
By
Erik Dustrude on 01/04/2018
Assay Type: In Vitro
Species: Rat
Cell Line/Tissue: amygdala neurons
50uM used to antagonize NMDA receptors to isolate AMPA current.
5 minutes perfusion at ~1.5ml/min was sufficient for the full effect.
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