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AB146300

L 701324, glycine site NMDA receptor antagonist

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MW 363.8 Da, Purity >99%. Potent, selective glycine site NMDA receptor antagonist. Shows a reduced propensity to activate mesolimbic dopaminergic systems compared to MK 801 (ab120027). Shows long-acting anticonvulsant effects in vivo. Orally active.

View Alternative Names

AW490526, CP2D6_HUMAN, CPD6, CYP2D, CYP2D7AP, CYP2D7BP, CYP2D7P2, CYP2D8P2, CYP2DL1, CYPIID6, Cholesterol 25-hydroxylase, Cytochrome P450 2D6, Cytochrome P450 family 2 subfamily D member 6, Cytochrome P450 family 2 subfamily D polypeptide 6, Cytochrome P450-DB1, Debrisoquine 4-hydroxylase, EB11, EIEE27, EPND, FESD, GRIN 2A, GRIN 2B, GRIN3A, GRIN3B, GluN1, GluN2A, GluN2C, GluN2D, 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 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 ionotropic, 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 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, LKS, MGC142178, MGC142180, MRD6, MRD8, Microsomal monooxygenase, 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 subunit 3, N-methyl-D-aspartate receptor subunit NR1, NMD-R1, NMDA 1, NMDA 2D, NMDA NR2B, NMDA receptor 1, NMDA receptor subtype 2A, NMDA receptor subunit 3A, NMDA receptor subunit 3B, NMDAR, NMDAR2C, NMDAR2D, NMDE1_HUMAN, NMDE2_HUMAN, NMDE3_HUMAN, NMDE4_HUMAN, NMDZ1_HUMAN, NR1, NR2A, NR2B, NR2C, NR2D, NR3, OTTHUMP00000041930, OTTHUMP00000160135, OTTHUMP00000174531, P450 DB1, P450C2D, Xenobiotic monooxygenase, estrogen receptor binding CpG island, flavoprotein-linked monooxygenase, glutamate receptor ionotropic NMDA 2D, glutamate receptor ionotropic, NMDA 1, hNR 3, hNR2A

1 Images
Chemical Structure - L 701324, glycine site NMDA receptor antagonist (AB146300)
  • Chemical Structure

Lab

Chemical Structure - L 701324, glycine site NMDA receptor antagonist (AB146300)

2D chemical structure image of ab146300, L 701324, glycine site NMDA receptor antagonist

Key facts

CAS number

142326-59-8

Purity

>99%

Form

Solid

form

Molecular weight

363.8 Da

Molecular formula

C<sub>2</sub><sub>1</sub>H<sub>1</sub><sub>4</sub>ClNO<sub>3</sub>

PubChem

54682505

Nature

Synthetic

Solubility

Soluble in DMSO to 100 mM

Biochemical name

2(1H)-Quinolinone, 7-chloro-4-hydroxy-3-(3-phenoxyphenyl)-

Biological description

Potent, selective glycine site NMDA receptor antagonist. Shows a reduced propensity to activate mesolimbic dopaminergic systems compared to MK 801 (ab120027). Shows long-acting anticonvulsant effects in vivo. Orally active.

Canonical smiles

C1=CC=C(C=C1)OC2=CC=CC(=C2)C3=C(C4=C(C=C(C=C4)Cl)NC3=O)O

InChi

InChI=1S/C21H14ClNO3/c22-14-9-10-17-18(12-14)23-21(25)19(20(17)24)13-5-4-8-16(11-13)26-15-6-2-1-3-7-15/h1-12H,(H2,23,24,25)

InChiKey

FLVRDMUHUXVRET-UHFFFAOYSA-N

IUPAC Name

7-chloro-4-hydroxy-3-(3-phenoxyphenyl)-1H-quinolin-2-one

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
The product can be stored for up to 12 months

Supplementary information

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

The NMDA receptors which include subunits such as NMDAR2A NMDAR2B GluN2C NMDAR1 and others like NMDAR3A and 3B play a mechanical role in synaptic transmission and plasticity. These receptors known also as N-methyl-D-aspartate receptors exist predominantly in the central nervous system. They integrate into a calcium-permeable ion channel complex. NMDA receptors weigh approximately in the range of 140-180 kDa and they localize mainly within the postsynaptic membrane of neurons. Each subunit like NMDAR2A and 2B can impact the receptor's functional properties such as its ion permeability and modulation.
Biological function summary

NMDA receptors serve as critical components for excitatory neurotransmission in the brain. As part of a larger receptor complex they allow for calcium entry upon activation by glutamate and co-agonists like glycine. This action triggers downstream signaling pathways that influence synaptic plasticity essential for processes like learning and memory. The interaction between different subunits provides specificity in receptor assembly and function enabling varying receptor responses to synaptic events. For instance subunit composition can determine the receptor's open probability and response to antagonists.

Pathways

NMDA receptors integrate into the central signaling pathways of neuronal communication and plasticity particularly in processes like long-term potentiation (LTP). The receptor's activation leads to the opening of calcium channels allowing calcium influx into the neurons which then engages signaling proteins such as CaMKII and calcineurin. These signaling pathways orchestrate changes that strengthen or modify synaptic connections. The NMDA receptor activity complements the functions of other neurotransmitter systems like the AMPA receptor pathway highlighting the receptor's involvement in synaptic plasticity and overall brain function.

Malfunctioning or altered NMDA receptor activity associates with neurological conditions like Alzheimer's disease and schizophrenia. Aberrations in the receptor function can lead to disrupted synaptic transmission contributing to cognitive deficits observed in Alzheimer's. In schizophrenia NMDA receptor hypofunction is linked to symptoms like psychosis and cognitive impairment. Proteins like CYP2D6 can interact with medications targeting NMDA receptors influencing treatment efficacy and side effects in these disorders. Understanding NMDA receptor function assists in exploring therapeutic strategies to tackle these complex neurological diseases.

Product protocols

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