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Merck
CN

SML0416

TCN-201

≥98% (HPLC)

Synonym(s):

3-Chloro-4-fluoro-N-[(4-{[2-(phenylcarbonyl)hydrazino]carbonyl}phenyl)methyl]benzenesulfonamide

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About This Item

Empirical Formula (Hill Notation):
C21H17ClFN3O4S
CAS Number:
852918-02-6
Molecular Weight:
461.89
NACRES:
NA.77
PubChem Substance ID:
329825411
UNSPSC Code:
12352200
MDL number:
MFCD06683895

Key Documents

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Product Name

TCN-201, ≥98% (HPLC)

InChI

1S/C21H17ClFN3O4S/c22-18-12-17(10-11-19(18)23)31(29,30)24-13-14-6-8-16(9-7-14)21(28)26-25-20(27)15-4-2-1-3-5-15/h1-12,24H,13H2,(H,25,27)(H,26,28)

SMILES string

Fc1ccc(cc1Cl)S(=O)(=O)NCc2ccc(cc2)C(=O)NNC(=O)c3ccccc3

InChI key

FYIBXBFDXNPBSF-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL (clear solution)

storage temp.

2-8°C

Quality Level

100

Biochem/physiol Actions

TCN-201 is a NR2A-selective NMDAreceptor antagonist 1.
TCN-201 is a sulphonamide derivative, that negatively modulates glycine binding to the GluN1 (glutamate receptor subunit) subunit of the receptor.
TCN-201 is the first NMDA receptor antagonist that is specific for NR2A-subunit containing receptors. The pIC50 for NR2A NMDA receptors is 6.8. TCN-201has no effect on NR2B-containing receptors at concentrations up to 50 mM.

Features and Benefits

This compound is featured on the Glutamate Receptors (Ion Channel Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

wgk

WGK 3

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Central nervous system, Respiratory system

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000144861
0000105055
0000030582
0000030583

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Structural basis for negative allosteric modulation of GluN2A-containing NMDA receptors
Yi F, et al.
Neuron, 91(6), 1316-1329 (2016)
Jean-Baptiste Esmenjaud et al.
The EMBO journal, 38(2) (2018-11-07)
NMDA receptors (NMDARs) are glutamate-gated ion channels that are key mediators of excitatory neurotransmission and synaptic plasticity throughout the central nervous system. They form massive heterotetrameric complexes endowed with unique allosteric capacity provided by eight extracellular clamshell-like domains arranged as
TCN 201 selectively blocks GluN2A-containing NMDARs in a GluN1 co-agonist dependent but non-competitive manner
Edman S, et al.
Neuropharmacology, 63(3), 441-449 (2012)
Yong-Tao He et al.
European journal of pharmacology, 854, 62-69 (2019-04-06)
Src Homology 2 domain-containing protein tyrosine phosphatase 1 (SHP1) interacts specifically with GluN2A subunit of N-methyl-D-aspartate (NMDA) subtype of glutamate receptors in spinal cord dorsal horn. This molecular interaction is involved in the development of GluN2A-dependent spinal sensitization of nociceptive
Giacomo Sitzia et al.
Neuropharmacology, 174, 108136-108136 (2020-06-01)
In Parkinson's disease (PD) reduced levels of dopamine (DA) in the striatum lead to an abnormal circuit activity of the basal ganglia and an increased output through the substantia nigra pars reticulata (SNr) and the globus pallidus internal part. Synaptic
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