MW 197.13 Da, Purity >99%. Competitive NMDA receptor glutamate site antagonist. More active form of DL-AP5.
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- Cell reports methods 3:1005442023Functional imaging-guided cell selection for evolving genetically encoded fluorescent indicators.Applications:Unspecified applicationReactive species:Unspecified reactive speciesChang Lin,Lihao Liu,Peng ZouPubMed 37671014
- Molecular therapy. Methods & clinical development 30:1-132023Starburst amacrine cells amplify optogenetic visual restoration through gap junctions.Applications:Unspecified applicationReactive species:Unspecified reactive speciesYusaku Katada,Hiromitsu Kunimi,Naho Serizawa,Deokho Lee,Kenta Kobayashi,Kazuno Negishi,Hideyuki Okano,Kenji F Tanaka,Kazuo Tsubota,Toshihide KuriharaPubMed 37324975
- Frontiers in molecular neuroscience 16:11482192023Denervated mouse CA1 pyramidal neurons express homeostatic synaptic plasticity following entorhinal cortex lesion.Applications:Unspecified applicationReactive species:Unspecified reactive speciesMaximilian Lenz,Amelie Eichler,Pia Kruse,Phyllis Stöhr,Dimitrios Kleidonas,Christos Galanis,Han Lu,Andreas VlachosPubMed 37122623
- The Journal of neuroscience : the official journal of the Society for Neuroscience 43:3421-34382023Mitofusin 2 Sustains the Axonal Mitochondrial Network to Support Presynaptic Ca Homeostasis and the Synaptic Vesicle Cycle in Rat Hippocampal Axons.Applications:Unspecified applicationReactive species:Unspecified reactive speciesJason D Vevea,Edwin R ChapmanPubMed 36997314
- The Journal of neuroscience : the official journal of the Society for Neuroscience 43:3042-30602023Microglial Cytokines Mediate Plasticity Induced by 10 Hz Repetitive Magnetic Stimulation.Applications:Unspecified applicationReactive species:Unspecified reactive speciesAmelie Eichler,Dimitrios Kleidonas,Zsolt Turi,Maximilian Fliegauf,Matthias Kirsch,Dietmar Pfeifer,Takahiro Masuda,Marco Prinz,Maximilian Lenz,Andreas VlachosPubMed 36977586
- The Journal of neuroscience : the official journal of the Society for Neuroscience 43:2631-26522023Chronic Neuronal Inactivity Utilizes the mTOR-TFEB Pathway to Drive Transcription-Dependent Autophagy for Homeostatic Up-Scaling.Applications:Unspecified applicationReactive species:Unspecified reactive speciesYang Wang,Jingran Lin,Jiarui Li,Lu Yan,Wenwen Li,Xingzhi He,Huan MaPubMed 36868861
- Cell reports 41:1114842022Calcium-permeable AMPA receptors on AII amacrine cells mediate sustained signaling in the On-pathway of the primate retina.Applications:Unspecified applicationReactive species:Unspecified reactive speciesKumiko A Percival,Jacqueline Gayet,Roupen Khanjian,W Rowland Taylor,Teresa PuthusseryPubMed 36223749
- eLife 11:2022The Na/K pump dominates control of glycolysis in hippocampal dentate granule cells.Applications:Unspecified applicationReactive species:Unspecified reactive speciesDylan J Meyer,Carlos Manlio Díaz-García,Nidhi Nathwani,Mahia Rahman,Gary YellenPubMed 36222651
- Science advances 8:eabp92572022Distributed interfacing by nanoscale photodiodes enables single-neuron light activation and sensory enhancement in 3D spinal explants.Applications:Unspecified applicationReactive species:Unspecified reactive speciesAgnes Thalhammer,Mario Fontanini,Jiuyun Shi,Denis Scaini,Luca Recupero,Alexander Evtushenko,Ying Fu,Suraj Pavagada,Andrea Bistrovic-Popov,Ljiljana Fruk,Bozhi Tian,Laura BalleriniPubMed 35960795
- MRS bulletin 47:530-5442022Functional imaging of brain organoids using high-density microelectrode arrays.Applications:Unspecified applicationReactive species:Unspecified reactive speciesManuel Schröter,Congwei Wang,Marco Terrigno,Philipp Hornauer,Ziqiang Huang,Ravi Jagasia,Andreas HierlemannPubMed 36120104
Key facts
- CAS number
- 79055-68-8
- Purity
- > 99%
- Form
- Solid
- Molecular weight
- 197.13 Da
- Molecular formula
- C5H12NO5P
- PubChem identifier
- 135342
- Nature
- Synthetic
Alternative names
AMPA 1, AMPA-selective glutamate receptor 1, AW490526, Chi-1, EB11, EIEE27, EPND, FESD, GLUH1, GRIA1_HUMAN, GRIN 2A, GRIN 2B, GRIN3A, GRIN3B, GluA1, GluN1, GluN2A, GluN2C, GluN2D, GluN3B, GluR-1, GluR-A, GluR-K1, Glutamate Receptor Ionotropic N Methyl D Aspartate 2B, Glutamate Receptor Ionotropic N Methyl D Aspartate 2C, Glutamate Receptor Ionotropic N Methyl D Aspartate subunit 2B, Glutamate [NMDA] receptor subunit 3A, Glutamate [NMDA] receptor subunit 3B, Glutamate [NMDA] receptor subunit epsilon-1, Glutamate [NMDA] receptor subunit epsilon-2, Glutamate [NMDA] receptor subunit epsilon-3, Glutamate [NMDA] receptor subunit epsilon-4, Glutamate [NMDA] receptor subunit zeta-1, Glutamate receptor, Glutamate receptor 1, Glutamate receptor ionotropic, Glutamate receptor ionotropic AMPA 1, Glutamate receptor ionotropic N methyl D aspartate 1, Glutamate receptor ionotropic N methyl D aspartate 2A, Glutamate receptor ionotropic N methyl D aspartate 3B, Glutamate receptor ionotropic NMDA 3B, Glutamate receptor ionotropic NMDA2B, Glutamate receptor ionotropic, N-methyl-D aspartate, subunit 1, Glutamate receptor ionotropic, NMDA 2C, Glutamate receptor subunit epsilon 2, Glutamate receptor, ionotropic, N-methyl D-aspartate 2D, Glutamate receptor, ionotropic, NMDA2B (epsilon 2), Grin2c, Grin2d, HBGR1, LKS, MGC133252, MGC142178, MGC142180, MRD6, MRD8, N Methly D Aspartate Receptor Channel Subunit Epsilon 3, N methyl D asparate receptor channel subunit epsilon 2, N methyl D aspartate receptor channel subunit zeta 1, N methyl D aspartate receptor channel, subunit epsilon 1, N methyl D aspartate receptor subunit 2A, N methyl D aspartate receptor subunit 2B, N methyl D aspartate receptor subunit 2C, N methyl d aspartate receptor subunit 2D, N-methyl D-aspartate receptor subtype 2A, N-methyl D-aspartate receptor subtype 2B, N-methyl D-aspartate receptor subtype 2C, N-methyl D-aspartate receptor subtype 2D, N-methyl-D-aspartate receptor, N-methyl-D-aspartate receptor subtype 3A, N-methyl-D-aspartate receptor subtype 3B, N-methyl-D-aspartate receptor subunit 3, N-methyl-D-aspartate receptor subunit NR1, NMD-R1, NMD3A_HUMAN, NMD3B_HUMAN, NMDA 1, NMDA 2D, NMDA NR2B, NMDA receptor 1, NMDA receptor subtype 2A, NMDA receptor subunit 3B, NMDA type glutamate receptor subunit NR3B, NMDAR, NMDAR-L, NMDAR-L1, NMDAR2C, NMDAR2D, NMDAR3A, NMDAR3B, NMDE1_HUMAN, NMDE2_HUMAN, NMDE3_HUMAN, NMDE4_HUMAN, NMDZ1_HUMAN, NR1, NR2A, NR2B, NR2C, NR2D, NR3, OTTHUMP00000041930, OTTHUMP00000160135, OTTHUMP00000160643, OTTHUMP00000165781, OTTHUMP00000174531, OTTHUMP00000224241, OTTHUMP00000224242, OTTHUMP00000224243, estrogen receptor binding CpG island, glutamate receptor ionotropic NMDA 2D, glutamate receptor ionotropic, NMDA 1, hNR 3, hNR2A
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MW 197.13 Da, Purity >99%. Competitive NMDA receptor glutamate site antagonist. More active form of DL-AP5.
Key facts
- CAS number
- 79055-68-8
- Purity
- > 99%
- Form
- Solid
- Molecular weight
- 197.13 Da
- Molecular formula
- C5H12NO5P
- PubChem identifier
- 135342
- Nature
- Synthetic
- Biochemical name
- 5-Phosphono-D-norvaline
- Biological description
Competitive NMDA receptor glutamate site antagonist. More active form of DL-AP5.
- Canonical SMILES
- C(CC(C(=O)O)N)CP(=O)(O)O
- Isomeric SMILES
- C(C[C@H](C(=O)O)N)CP(=O)(O)O
- InChI
- InChI=1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)/t4-/m1/s1
- InChIKey
- VOROEQBFPPIACJ-SCSAIBSYSA-N
- IUPAC name
- (2R)-2-amino-5-phosphonopentanoic acid
Storage
- Shipped at conditions
- Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
- +4°C
- Appropriate long-term storage conditions
- +4°C
- Storage information
- Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary info
- This supplementary information is collated from multiple sources and compiled automatically.
- Activity summary
The N-Methyl-D-Aspartate Receptor (NMDAR) subunits such as NMDAR2A NMDAR2B GluN2C NMDAR1 GluN2D NR3A and NR3B are key components of glutamate receptors also including the AMPA subtype Glutamate Receptor 1. These receptors are ionotropic and mediate synaptic transmission in the central nervous system. They are expressed in the brain particularly in regions such as the hippocampus and cortex. NMDAR1 also known as GluN1 serves as an obligatory subunit required for functional receptor assembly. The mass of NMDAR subunits varies; for example the GluN1 subunit has an approximate mass of 120 kDa.
- Biological function summary
These glutamate receptor subunits forming part of NMDAR and AMPA receptor complexes modulate synaptic plasticity which underlies learning and memory. NMDARs are tetrameric complexes composed mostly of two GluN1 subunits combined with two region-specific GluN2 (A-D) or GluN3 (A B) subunits creating diversity in function and pharmacological characteristics. The AMPA receptor primarily built of GluA1 through GluA4 subunits contributes to fast excitatory neurotransmission. Together these receptors regulate calcium ion flow into neurons impacting cellular events essential for neural communication and adaptation.
- Pathways
NMDARs and AMPA receptors integrate into key neural and signaling pathways such as the long-term potentiation pathway which is essential for memory formation. NMDAR activation allows calcium influx necessary for initiating intracellular signaling cascades. The interactions with proteins like CaMKII and synaptic scaffolds like PSD-95 illustrate the role of these receptors in synaptic and protein signaling networks that adjust synaptic strength.
- Associated diseases and disorders
NMDAR and AMPA receptors have massive implications in neurodegenerative diseases like Alzheimer's and neuropsychiatric disorders such as schizophrenia. Dysregulation in NMDAR function possibly through inadequate blockade by antagonists like D-AP5 or D-APV links to excitotoxicity a condition contributing to neuronal death as seen in Alzheimer's. In schizophrenia altered NMDAR signaling is connected to cognitive dysfunction and both NMDAR and AMPA may serve as therapeutic targets.
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4 product images
Chemical Structure - D-AP5, NMDA glutamate site antagonist (ab120003)
2D chemical structure image of ab120003, D-AP5, NMDA glutamate site antagonist
Image from Barker M et al., Plos One, 7(5), e35955. Fig 1,; doi: 10.1371/journal.pone.0035955Cellular Activation - D-AP5, NMDA glutamate site antagonist (ab120003)
(A) Photomicrograph of a DCN fusiform cell filled with lucifer yellow (top) and whole cell voltage clamp recording of this fusiform cell while stimulating the LVN (bottom). (B) Photomicrograph of a DCN granule cell filled with lucifer yellow (top) and whole cell voltage clamp recording of this granule cell while stimulating the LVN (bottom). Both cells were held at -68 mV and the LVN was stimulated at 0.3 Hz. Glutamatergic EPSCs are represented in black and are blocked by 50 μm D-AP5 and 10 μm NBQX (traces in red). Each trace represents an average of 10-20 single traces. The arrowhead represents the artifact of stimulus that has been removed for clarity. Scale bar: (A) 50 μm, (B) 20 μm.
Image from Herman MA et al., PLoS One. 2011;6(11):e26501. Fig 2(A).; doi: 10.1371/journal.pone.0026501. Reproduced under the Creative Commons license http://creativecommons.org/licenses/by/4.0/Functional Studies - D-AP5, NMDA glutamate site antagonist (ab120003)
Averaged Ca2+ transients (500 Hz line scans) evoked by 40 ms voltage step in a dendrite (left) and spine (right) in control (black), D-AP5 (red, 10 µM), after a 10 min washout of D-AP5 (green), and in 5 µM NMDA (blue). Mibefradil (20 µM), nimodipine (20 µM) and TTX (0.5 µM) were present throughout.
Image from Brady JD et al., Neuroscience. 2010;168(1):108-17. Fig 3.; doi: 10.1016/j.neuroscience.2010.03.009 with permission from Elsevier.Functional Studies - D-AP5, NMDA glutamate site antagonist (ab120003)
Representative voltage-clamp recording (Vh= −60 mV, ECl−=+8 mV) of a Purkinje cells response to simulated ischemia and sequential block of glutamate receptors and GABAA receptors.
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