mGluR5 Antagonist, MTEP

Name: mGluR5 Antagonist, MTEP
Brand: MM

The mGluR5 Antagonist, MTEP, also referenced under CAS 329205-68-7, controls the biological activity of mGluR5. This small molecule/inhibitor is primarily used for Neuroscience applications.

Synonym(s):

mGluR5 Antagonist, MTEP, 3-((2-Methyl-1,3-thiazol-4-yl)ethynyl)pyridine

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₈N₂S

CAS Number:

329205-68-7

Molecular Weight:

200.26

MDL number:

MFCD05260891

UNSPSC Code:

12352200

NACRES:

NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze
protect from light

color

white to yellow

solubility

methanol: 1 mg/mL
DMSO: 5 mg/mL

shipped in

ambient

storage temp.

2-8°C

SMILES string

[s]1c(nc(c1)C#Cc2cnccc2)C

InChI

1S/C11H8N2S/c1-9-13-11(8-14-9)5-4-10-3-2-6-12-7-10/h2-3,6-8H,1H3

InChI key

NRBNGHCYDWUVLC-UHFFFAOYSA-N

General description

A brain-permeable (thiazole-pyridine)alkyne compound that acts as a potent, selective and non-competitive mGluR5 (metabotropic glutamate receptor subtype-5) antagonist (IC₅₀ = 5 nM in Ca²⁺-flux assay; K_i = 16 nM) with in vivo anxiolytic activity in a rodent model (ED₅₀ = 1 mg/kg, ip and 7 mg/kg, po). Devoid of any side effects seen with MPEP and benzodiazepines. Reported to weakly affect the activities of other enzymes and receptors tested (IC₅₀ = 30 µM for MAO-A, >100 µM for mGlu1R, 2R & 7R, and >300 µM for NR2BR).

Biochem/physiol Actions

Cell permeable: yes

Primary Target
mGluR5

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 5 nM in Ca2+-flux assay

Target K_i: 16 nM for mGluR5 (metabotropic glutamate receptor subtype-5)

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Bradbury, M.J., et al. 2005. J. Pharmacol. Exp. Ther.313, 395.
Busse, C.S., et al. 2004. Neuropsychopharmacology29, 1971.
Roppe, J.R., et al. 2004. Bioorg. Med. Chem. Lett.14, 3993.
Klodzinska, A., et al. 2004. Neuropharmacology47, 342.
Cosford, N.D.P., et al. 2003. J. Med. Chem.46, 204.
Brodkin, J., et al. 2002. Eur. J. Neurosci.16, 2241.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Metabotropic glutamate receptor mGlu5 is a mediator of appetite and energy balance in rats and mice.

Margaret J Bradbury et al.

The Journal of pharmacology and experimental therapeutics, 313(1), 395-402 (2004-12-14)

The metabotropic glutamate receptor subtype mGlu5 modulates central reward pathways. Many transmitter systems within reward pathways affect feeding. We examined the potential role of mGlu5 in body weight regulation using genetic and pharmacological approaches. Adult mice lacking mGlu5, mGluR5-/-, weighed

5-[(2-Methyl-1,3-thiazol-4-yl)ethynyl]-2,3'-bipyridine: a highly potent, orally active metabotropic glutamate subtype 5 (mGlu5) receptor antagonist with anxiolytic activity.

Jeffrey R Roppe et al.

Bioorganic & medicinal chemistry letters, 14(15), 3993-3996 (2004-07-01)

Structure-activity relationship studies leading to the discovery of a new, orally active mGlu5 receptor antagonist are described. The title compound, 5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]-2,3'-bipyridine, is highly potent in vitro, has good in vivo receptor occupancy, and is efficacious in the rat fear-potentiated startle

The behavioral profile of the potent and selective mGlu5 receptor antagonist 3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridine (MTEP) in rodent models of anxiety.

Chris S Busse et al.

Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 29(11), 1971-1979 (2004-08-12)

Previous reports have demonstrated the anxiolytic effect of the potent and systemically active metabotropic glutamate subtype 5 (mGlu5) receptor antagonist 2-methyl-6-(phenylethynyl)pyridine (MPEP) in rodents. Here, we present evidence for the anxiolytic activity of a novel mGlu5 receptor antagonist, 3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridine (MTEP)

Reduced stress-induced hyperthermia in mGluR5 knockout mice.

J Brodkin et al.

The European journal of neuroscience, 16(11), 2241-2244 (2002-12-11)

It hs been suggested that metabotropic glutamate receptor subtype 5 (mGluR5) play a role in the expression of anxiety, based on anxiolytic-like effects of the selective mGluR5 antagonist MPEP (2-methyl-6-(phenylethynyl)pyridine) in rodent models of anxiety, including stress-induced hyperthermia (SIH). To

Anxiolytic-like effects of MTEP, a potent and selective mGlu5 receptor agonist does not involve GABA(A) signaling.

Aleksandra Klodzinska et al.

Neuropharmacology, 47(3), 342-350 (2004-07-28)

Several lines of evidence suggest a crucial involvement of glutamate in the mechanism of action of anxiolytic drugs including the involvement of group I metabotropic glutamate (mGlu) receptors. Given the recent discovery of a selective and brain penetrable mGlu5 receptor

View All Related Papers

Glutamate is an excitatory neurotransmitter found in the synaptic vesicles of glutamatergic synapses. The post-synaptic neurons in these synapses contain ionotropic and metabotropic glutamate receptors. Glutamate binds to AMPA (α-amino-3-hydroxy-5- methylisoxazole-4-propionic acid) subtype glutamate receptors, leading to sodium influx into the post-synaptic cell and resulting in neuronal excitability and synaptic transmission. The NMDA (N-methyl-d-aspartate) subtype glutamate receptors, on the other hand, regulate synaptic plasticity, and can influence learning and memory. The metabotropic g-protein coupled mGluRs modulate downstream calcium signaling pathways and indirectly influence the synapse’s excitability. The synaptic architecture includes intracellular scaffolding proteins (PSD-95, GRIP), intercellular cell adhesion molecules (NCAMs, N-Cadherins), and a variety of signaling proteins (CaMKII/PKA, PP1/PP2B). Processes critical for synaptic transmission and plasticity are influenced by these molecules and their interactions. When the function of these molecules is disrupted, it leads to synaptic dysfunction and degeneration, and can contribute to dementia as seen in Alzheimer’s disease.

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