MW 252.2 Da. Highly potent, competitive NMDA antagonist; more active enantiomer of (RS)-CPP (ab120160). (Ki values are 0.04, 0.3, 0.6 and 2.0 μM at NR1/NR2A, NR1/NR2B, NR1/NR2C and NR1/NR2D, respectively).
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- Cell reports 42:1120392023Circadian regulation of dentate gyrus excitability mediated by G-protein signaling.Applications:Unspecified applicationReactive species:Unspecified reactive speciesJose Carlos Gonzalez,Haeun Lee,Angela M Vincent,Angela L Hill,Lacy K Goode,Gwendalyn D King,Karen L Gamble,Jacques I Wadiche,Linda Overstreet-WadichePubMed 36749664
- Cell reports 39:1107952022Serotonin receptors contribute to dopamine depression of lateral inhibition in the nucleus accumbens.Applications:Unspecified applicationReactive species:Unspecified reactive speciesDennis A Burke,Veronica A AlvarezPubMed 35545050
- eLife 10:2021Purkinje cell outputs selectively inhibit a subset of unipolar brush cells in the input layer of the cerebellar cortex.Applications:Unspecified applicationReactive species:Unspecified reactive speciesChong Guo,Stephanie Rudolph,Morgan E Neuwirth,Wade G RegehrPubMed 34369877
- eLife 10:2021Incomplete removal of extracellular glutamate controls synaptic transmission and integration at a cerebellar synapse.Applications:Unspecified applicationReactive species:Unspecified reactive speciesTimothy S Balmer,Carolina Borges-Merjane,Laurence O TrussellPubMed 33616036
- The Journal of neuroscience : the official journal of the Society for Neuroscience 41:594-6122020Purinergic Signaling Controls Spontaneous Activity in the Auditory System throughout Early Development.Applications:Unspecified applicationReactive species:Unspecified reactive speciesTravis A Babola,Sally Li,Zhirong Wang,Calvin J Kersbergen,Ana Belén Elgoyhen,Thomas M Coate,Dwight E BerglesPubMed 33303678
- eLife 9:2020Cerebellar and vestibular nuclear synapses in the inferior olive have distinct release kinetics and neurotransmitters.Applications:Unspecified applicationReactive species:Unspecified reactive speciesJosef Turecek et. al.PubMed 33259288
- Cell reports 33:1083382020Cerebellum-Specific Deletion of the GABA Receptor δ Subunit Leads to Sex-Specific Disruption of Behavior.Applications:Unspecified applicationReactive species:Unspecified reactive speciesStephanie Rudolph,Chong Guo,Stan L Pashkovski,Tomas Osorno,Winthrop F Gillis,Jeremy M Krauss,Hajnalka Nyitrai,Isabella Flaquer,Mahmoud El-Rifai,Sandeep Robert Datta,Wade G RegehrPubMed 33147470
- eLife 9:2020Parvalbumin interneurons provide spillover to newborn and mature dentate granule cells.Applications:Unspecified applicationReactive species:Unspecified reactive speciesRyan J Vaden et. al.PubMed 32602839
- eLife 9:2020Loss of Doc2b does not influence transmission at Purkinje cell to deep nuclei synapses under physiological conditions.Applications:Unspecified applicationReactive species:Unspecified reactive speciesMehak M Khan et. al.PubMed 32347796
Key facts
- CAS number
- 126453-07-4
- Form
- Solid
- Molecular weight
- 252.2 Da
- Molecular formula
- C8H17N2O5P
- PubChem identifier
- 6603754
- Nature
- Synthetic
Alternative names
AMPA 1, AMPA 2, AMPA 3, AMPA 4, AMPA-selective glutamate receptor 1, AMPA-selective glutamate receptor 2, AMPA-selective glutamate receptor 3, AMPA-selective glutamate receptor 4, AW490526, Chi-1, EB11, EIEE27, EPND, FESD, GLUH1, GLUK3, GLUR4C, GRIA1_HUMAN, GRIA2_HUMAN, GRIA3_HUMAN, GRIA4_HUMAN, GRIN 2A, GRIN 2B, GRIN3A, GRIN3B, GluA 4, GluA1, GluA2, GluA3, GluN1, GluN2A, GluN2C, GluN2D, GluN3B, GluR-1, GluR-2, GluR-3, GluR-4, GluR-A, GluR-B, GluR-C, GluR-D, GluR-K1, GluR-K2, GluR-K3, 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 Receptor Ionotropic N methyl D aspartate 3A, 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 ionotropic receptor AMPA type subunit 3, Glutamate receptor, Glutamate receptor 1, Glutamate receptor 2, Glutamate receptor 3, Glutamate receptor 4, Glutamate receptor C, Glutamate receptor ionotrophic AMPA 3, Glutamate receptor ionotrophic AMPA 4, Glutamate receptor ionotropic, Glutamate receptor ionotropic AMPA 1, Glutamate receptor ionotropic AMPA 2, 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 3, Glutamate receptor subunit epsilon 2, Glutamate receptor, ionotropic, AMPA 3, Glutamate receptor, ionotropic, N-methyl D-aspartate 2D, Glutamate receptor, ionotropic, NMDA2B (epsilon 2), Grin2c, Grin2d, HBGR1, HBGR2, Ionotrophic Glutamate Receptor, Ionotropic Glutamate receptor 4, LKS, MGC133252, MGC142178, MGC142180, MRD6, MRD8, MRX94, 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 3A, 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, dJ1171F9.1, estrogen receptor binding CpG island, glutamate receptor ionotropic NMDA 2D, glutamate receptor ionotropic, NMDA 1, hNR 3, hNR2A
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MW 252.2 Da. Highly potent, competitive NMDA antagonist; more active enantiomer of (RS)-CPP (ab120160). (Ki values are 0.04, 0.3, 0.6 and 2.0 μM at NR1/NR2A, NR1/NR2B, NR1/NR2C and NR1/NR2D, respectively).
Key facts
- CAS number
- 126453-07-4
- Form
- Solid
- Molecular weight
- 252.2 Da
- Molecular formula
- C8H17N2O5P
- PubChem identifier
- 6603754
- Nature
- Synthetic
- Biochemical name
- (R)-4-(3-phosphonopropyl)piperazine-2-carboxylic acid
- Biological description
Highly potent, competitive NMDA antagonist; more active enantiomer of (RS)-CPP (ab120160). (Ki values are 0.04, 0.3, 0.6 and 2.0 μM at NR1/NR2A, NR1/NR2B, NR1/NR2C and NR1/NR2D, respectively).
- Canonical SMILES
- C1CN(CC(N1)C(=O)O)CCCP(=O)(O)O
- Isomeric SMILES
- C1CN(C[C@@H](N1)C(=O)O)CCCP(=O)(O)O
- InChI
- InChI=1S/C8H17N2O5P/c11-8(12)7-6-10(4-2-9-7)3-1-5-16(13,14)15/h7,9H,1-6H2,(H,11,12)(H2,13,14,15)/t7-/m1/s1
- InChIKey
- CUVGUPIVTLGRGI-SSDOTTSWSA-N
- IUPAC name
- (2R)-4-(3-phosphonopropyl)piperazine-2-carboxylic acid
Storage
- Shipped at conditions
- Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
- Ambient
- Appropriate long-term storage conditions
- Ambient
- 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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2 product images
Chemical Structure - (R)-CPP, NMDA antagonist (ab120159)
2D chemical structure image of ab120159, (R)-CPP, NMDA antagonist
Herman et al PLoS One. 2011;6(11):e26501. doi: 10.1371/journal.pone.0026501. Epub 2011 Nov 1. Fig 3. Reproduced under the Creative Commons license http://creativecommons.org/licenses/by/4.0/Functional Studies - (R)-CPP, NMDA antagonist (ab120159)
Transporter blockade does not reveal an ambient glutamate concentration gradient between extracellular compartments.A. Average Ca2+ increase in a spine during a 40 ms voltage step, with iontophoresis of L-aspartate (black), without iontophoresis (red), a second L-aspartate application (gray), L-aspartate in the presence of 100 μM TBOA (blue), and TBOA alone (green).
B. Comparison of spine Ca2+ transients in each condition, normalized to the first response to L-aspartate iontophoresis (n = 5). Error bars indicate SEM. Significance determined by Friedman ANOVA with Conover posthoc test: *p<0.05; **p<0.01; ***p<0.001.
If the extrasynaptic glutamate concentration is higher than that in the cleft because transporters prevent diffusion of glutamate into the synapse, blocking transporters should result in a large Ca2+ increase in the spine as extrasynaptic glutamate rushes into the cleft and activates synaptic NMDARs. Spines exhibited a Ca2+ increase during a 40 ms depolarization with iontophoresis of the glutamate transporter substrate and NMDAR agonist, L-aspartate (A; black and gray traces), confirming the presence of NMDARs. However, TBOA (100 μM) did not increase the Ca2+ transient in the same spines during the 40 ms depolarization when compared to the control voltage step without L-aspartate iontophoresis (See image compare green and red traces; 20.6±13.62%; p>0.5; n = 5;). TBOA was effective in blocking transporters, however, as the NMDAR-mediated Ca2+ signal evoked by iontophoresis of L-aspartate was increased in the presence of TBOA (See image). This result indicates that glutamate transporters do not normally generate a concentration gradient of ambient glutamate between extrasynaptic and synaptic extracellular compartments.
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