DL-AP5

Cat. No. 0105

DL-AP5 C5H12NO5P [76326-31-3]

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Alternative Name: DL-APV

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

Biological Activity

Potent NMDA antagonist. Separate isomers D-AP5 (Cat. No. 0106), L-AP5 (Cat. No. 0107) and sodium salt DL-AP5 Sodium salt (Cat. No. 3693) 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.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

Certificate of Analysis / Product Datasheet
Select another batch:

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.

If you know of a relevant reference for this product please let us know.

Citations are publications that use Tocris products. Selected citations for DL-AP5 include:

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.

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.

Bajo et al (2015) IL-1 interacts with ethanol effects on GABAergic transmission in the mouse central amygdala. Front Pharmacol 6 49. PMID: 25852553.

Ferreira et al (2015) GluN2B-Containing NMDA Receptors Regulate AMPA Receptor Traffic through Anchoring of the Synaptic Proteasome. J Neurosci 35 8462. PMID: 26041915.

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.

Liu et al (2015) Muscarinic receptors modulate dendrodendritic inhibitory synapses to sculpt glomerular output. J Neurosci 35 5680. PMID: 25855181.

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.

Sarro et al (2015) Cortical Synaptic Inhibition Declines during Auditory Learning. J Neurosci 35 6318. PMID: 25904785.

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.

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.

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 Dopamine in the Basolateral Amygdala. Front Pediatr 2 46. PMID: 24904907.

Granger and Nicoll (2014) LTD expression is independent of glutamate receptor subtype. Front Synaptic Neurosci 6 15. PMID: 25071549.

Halff et al (2014) A novel mechanism for nicotinic potentiation of glutamatergic synapses. J Neurosci 34 2051. PMID: 24501347.

Lee et al (2014) Synapse elimination and learning rules co-regulated by MHC class I H2-Db. Nature 509 195. PMID: 24695230.

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.

Röther et al (2014) Dynamic properties of the alkaline vesicle population at hippocampal synapses. PLoS One 9 e102723. PMID: 25079223.

Rovó et al (2014) Phasic, nonsynaptic GABA-A receptor-mediated inhibition entrains thalamocortical oscillations. J Neurosci 34 7137. PMID: 24849349.

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.

Wilcox et al (2014) Repeated binge-like ethanol drinking alters ethanol drinking patterns and depresses striatal GABAergic transmission. Neuropsychopharmacology 39 579. PMID: 23995582.

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.

Gkogkas et al (2013) Autism-related deficits via dysregulated eIF4E-dependent translational control. Nature 493 371. PMID: 23172145.

Rehak et al (2013) Low voltage activation of KCa1.1 current by Cav3-KCa1.1 complexes. PLoS One 8 e61844. PMID: 23626738.

Thayer et al (2013) Increased neuronal activity fragments the Golgi complex. Proc Natl Acad Sci U S A 110 1482. PMID: 23297202.

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.

Chacón et al (2012) Focal adhesion kinase regulates actin nucleation and neuronal filopodia formation during axonal growth. Development 139 3200. PMID: 22872087.

Lau and Murthy (2012) Activity-dependent regulation of inhibition via GAD67. J Neurosci 32 8521. PMID: 22723692.

McKeown et al (2012) Disruption of Eaat2b, a glutamate transporter, results in abnormal motor behaviors in developing zebrafish. Dev Biol 362 162. PMID: 22094018.

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.

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.

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.

Vivar et al (2012) Mixed electrical-chemical transmission between hippocampal mossy fibers and pyramidal cells. Eur J Neurosci 35 76. PMID: 22151275.

Reali et al (2011) GABAergic signalling in a neurogenic niche of the turtle spinal cord. J Physiol 589 5633. PMID: 21911613.

Tang et al (2011) Neto1 is an auxiliary subunit of native synaptic kainate receptors. J Neurosci 31 10009. PMID: 21734292.

Wang et al (2011) Functional NMDA receptors at axonal growth cones of young hippocampal neurons. J Neurosci 31 9289. PMID: 21697378.

Yang et al (2011) SynGAP moves out of the core of the postsynaptic density upon depolarization. Neuroscience 192 132. PMID: 21736925.

Zhao et al (2011) Homeostatic synaptic plasticity through changes in presynaptic calcium influx. J Neurosci 31 7492. PMID: 21593333.

Zhong et al (2011) Neurogranin phosphorylation fine-tunes long-term potentiation. Eur J Neurosci 33 244. PMID: 21198977.

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.

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.

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.

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.

Zheng et al (2010) SAP102 is a highly mobile MAGUK in spines. J Neurosci 30 4757. PMID: 20357126.

Sipilä et al (2009) Compensatory enhancement of intrinsic spiking upon NKCC1 disruption in neonatal hippocampus. J Neurosci 29 6982. PMID: 19474325.

Zang et al (2009) A mouse model of the human Fragile X syndrome I304N mutation. PLoS Genet 5 e1000758. PMID: 20011099.

Baltan et al (2008) White matter vulnerability to ischemic injury increases with age because of enhanced excitotoxicity. J Neurosci 28 1479. PMID: 18256269.

Brill and Huguenard (2008) Sequential changes in AMPA receptor targeting in the developing neocortical excitatory circuit. J Neurosci 28 13918. PMID: 19091980.

Costa et al (2008) Electrophysiology and pharmacology of striatal neuronal dysfunction induced by mitochondrial complex I inhibition. J Neurosci 28 8040. PMID: 18685029.

Kash et al (2008) Dopamine enhances fast excitatory synaptic transmission in the extended amygdala by a CRF-R1-dependent process. J Neurosci 28 13856. PMID: 19091975.

Maher and Westbrook (2008) Co-transmission of dopamine and GABA in periglomerular cells. J Neurophysiol 99 1559. PMID: 18216231.

Manning et al (2008) NMDA receptor blockade with memantine attenuates white matter injury in a rat model of periventricular leukomalacia. J Neurosci 28 6670. PMID: 18579741.

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.

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.

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.

Gómez-Lira et al (2005) Programmed and induced phenotype of the hippocampal granule cells. J Neurosci 25 6939. PMID: 16049169.

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.

Melyan et al (2004) Metabotropic regulation of intrinsic excitability by synaptic activation of kainate receptors. J Neurosci 24 4530. PMID: 15140923.

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.

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.

Do you know of a great paper that uses DL-AP5 from Tocris? If so please let us know.show all ▼show less ▲

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