JavaScript is disabled in your browser. Please enable JavaScript to view this website.
AB144495

(R)-CPP (mM/ml), NMDA antagonist

Be the first to review this product! Submit a review

|

(8 Publications)

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).

View 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

1 Images
Chemical Structure - (R)-CPP (mM/ml), NMDA antagonist (AB144495)
  • Chemical Structure

Lab

Chemical Structure - (R)-CPP (mM/ml), NMDA antagonist (AB144495)

2D chemical structure image of ab144495, (R)-CPP (mM/ml), NMDA antagonist

Key facts

CAS number

126453-07-4

Form

Solid

form

Molecular weight

252.2 Da

Molecular formula

C<sub>8</sub>H<sub>1</sub><sub>7</sub>N<sub>2</sub>O<sub>5</sub>P

PubChem

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

Properties and storage information

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 information

This supplementary information is collated from multiple sources and compiled automatically.

The target 'Glutamate Receptor' also known by its subtypes like NMDAR2A NMDAR2B GluN2C NMDAR1 and others serves as an essential component in synaptic transmission in the central nervous system. These receptors are ionotropic meaning they form ion channels and are known for binding to the neurotransmitter glutamate. The GluN2 subunits including GluN2A GluN2B GluN2C and GluN2D contribute to the heteromeric complexes of NMDAR (N-methyl-D-aspartate receptors) which have a role in excitatory neurotransmission. The mass of these receptors varies with their subunits generally within the range of 105-180 kDa. They are expressed widely in the brain with each subtype showing distinct patterns of expression in regions like the hippocampus cortex and cerebellum.
Biological function summary

These glutamate receptors play a pivotal role in synaptic plasticity which underpins learning and memory. Within synaptic complexes NMDARs form associations with scaffolding proteins and signal transduction molecules facilitating cellular responses to activity. The AMPA-type glutamate receptors including Glutamate Receptor 1 (GluA1) and Glutamate Receptor 3 (GluA3) collaborate with NMDARs in synaptic transmission by controlling the fast component of excitatory postsynaptic currents. These interactions enable the receptors to modulate synaptic strength and contribute to the maintenance of neural circuits.

Pathways

These ionotropic glutamate receptors function prominently within the glutamatergic signaling pathway and the calcium signaling pathway. The NMDARs are known to influence calcium influx pivotal for downstream activation of signaling cascades such as CaMKII and MAPK. Related proteins like PSD-95 form complexes with NMDARs mediating cellular responses important for signal transduction. These pathways highlight glutamate receptors' roles in pre- and post-synaptic cellular responses affecting numerous downstream effects that influence neural plasticity and survival.

Disruptions in the function of these glutamate receptors are associated with neurodegenerative diseases and psychiatric disorders. For instance NMDAR malfunction links to Alzheimer's disease due to its involvement in synaptic failure and resultant cognitive deficits. Dysfunctional glutamatergic signaling also connects to schizophrenia where altered NMDAR activity affects neurotransmission and can contribute to symptoms. Proteins like GluA1 also interact in these contexts impacting synaptic plasticity further and potentially exacerbating disease progression through maladaptive synaptic changes.

Product protocols

Publications (8)

Recent publications for all applications. Explore the full list and refine your search

Journal of neuroinflammation 22:98 PubMed40181459

2025

Microglia determine an immune-challenged environment and facilitate ibuprofen action in human retinal organoids.

Applications

Unspecified application

Species

Unspecified reactive species

Verena Schmied,Medina Korkut-Demirbaş,Alessandro Venturino,Juan Pablo Maya-Arteaga,Sandra Siegert

Function (Oxford, England) 6: PubMed40042980

2025

High-Salt Diet Increases Suprachiasmatic Neuronal Excitability Through Endothelin Receptor Type B Signaling.

Applications

Unspecified application

Species

Unspecified reactive species

Jodi R Paul,Megan K Rhoads,Anna Elam,David M Pollock,Karen L Gamble

Nature neuroscience 16:632-8 PubMed23542690

2013

Strengthening the accumbal indirect pathway promotes resilience to compulsive cocaine use.

Applications

Unspecified application

Species

Unspecified reactive species

Roland Bock,J Hoon Shin,Alanna R Kaplan,Alice Dobi,Eric Markey,Paul F Kramer,Christina M Gremel,Christine H Christensen,Martin F Adrover,Veronica A Alvarez

The Journal of neuroscience : the official journal of the Society for Neuroscience 33:4768-81 PubMed23486948

2013

Rapid, activity-independent turnover of vesicular transmitter content at a mixed glycine/GABA synapse.

Applications

Unspecified application

Species

Unspecified reactive species

Pierre F Apostolides,Laurence O Trussell

PloS one 6:e26501 PubMed22069455

2011

Distribution of extracellular glutamate in the neuropil of hippocampus.

Applications

Unspecified application

Species

Unspecified reactive species

Melissa A Herman,Ben Nahir,Craig E Jahr

The Journal of neuroscience : the official journal of the Society for Neuroscience 31:7450-5 PubMed21593328

2011

Excitatory modulation in the cochlear nucleus through group I metabotropic glutamate receptor activation.

Applications

Unspecified application

Species

Unspecified reactive species

Soham Chanda,Matthew A Xu-Friedman

The Journal of neuroscience : the official journal of the Society for Neuroscience 31:565-74 PubMed21228165

2011

Axonal GABAA receptors increase cerebellar granule cell excitability and synaptic activity.

Applications

Unspecified application

Species

Unspecified reactive species

Jason R Pugh,Craig E Jahr

The Journal of neuroscience : the official journal of the Society for Neuroscience 29:10104-10 PubMed19675244

2009

Glycinergic projection neurons of the cerebellum.

Applications

Unspecified application

Species

Unspecified reactive species

Martha W Bagnall,Brian Zingg,Alexandra Sakatos,Setareh H Moghadam,Hanns Ulrich Zeilhofer,Sascha du Lac
View all publications

Product promise

We are committed to supporting your work with high-quality reagents, and we're here for you every step of the way. In the unlikely event that one of our products does not perform as expected, you're protected by our Product Promise.
For full details, please see our Terms & Conditions

Please note: All products are 'FOR RESEARCH USE ONLY. NOT FOR USE IN DIAGNOSTIC OR THERAPEUTIC PROCEDURES'.

For licensing inquiries, please contact partnerships@abcam.com