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SML2306

Sigma-Aldrich

CTEP

≥98% (HPLC)

Sinônimo(s):

2-Chloro-4-((2,5-dimethyl-1-(4-(trifluoromethoxy)phenyl)-1H-imidazol-4-yl)ethynyl)pyridine, 2-Chloro-4-[2-[2,5-dimethyl-1-[4-(trifluoromethoxy)phenyl]-1H-imidazol-4-yl]ethynyl]pyridine, RO4956371

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About This Item

Fórmula empírica (Notação de Hill):
C19H13ClF3N3O
Número CAS:
871362-31-1
Peso molecular:
391.77
Número MDL:
MFCD22665726
Código UNSPSC:
12352200
NACRES:
NA.77

R$ 1.005,00

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Ensaio

≥98% (HPLC)

Formulário

powder

cor

white to beige

solubilidade

DMSO: 2 mg/mL, clear

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

CC1=C(C#CC2=CC(Cl)=NC=C2)N=C(C)N1C3=CC=C(OC(F)(F)F)C=C3

InChI

1S/C19H13ClF3N3O/c1-12-17(8-3-14-9-10-24-18(20)11-14)25-13(2)26(12)15-4-6-16(7-5-15)27-19(21,22)23/h4-7,9-11H,1-2H3

chave InChI

GOHCTCOGYKAJLZ-UHFFFAOYSA-N

Ações bioquímicas/fisiológicas

Brain-penetrant, orally active, potent and selective mGluR5 (mGlu5) negative allosteric modulator & inverse agonist.
CTEP (RO4956371) may be used as a therapeutic to reduce hippocampal long-term depression, protein synthesis, and audiogenic seizures in the fragile X mental retardation 1 (Fmr1) knockout mouse.[1]
CTEP is a high-affinity, orally active, potent and selective metabotropic glutamate receptor 5 (mGlu5 or mGluR5) negative allosteric modulator (NAM) and inverse agonist (human/mouse/rat mGlu5 Kd = 1.7/1.8/1.5 nM; IC50 against quisqualate stimulation = 6.4/16.8/8/8 by IP accumulation or 11.4/42/4/6.9 by Ca2+ mobilization using human/mouse/rat mGlu5 HEK293 transfectants; IC50 = 40.1 nM against constitutive IP level in human mGlu5 HEK293) with >1000-fold selectivity over 103 molecular targets, including all known mGluRs. CTEP is an excellent tool compound for long-term in vivo studies (in mice and rats) with good pharmacokinetic properties (B/P ratio = 2.6, oral bioavailability ~100%, T1/2 ~18 hrs post 4.5 mg/kg p.o. in mice) and reported to display 30- to 100-fold higher in vivo potency than MPEP and fenobam in two rodent behavioral models sensitive to antianxiety drugs.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number
0000204465

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Jifang Tao et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 36(47), 11946-11958 (2016-11-25)
Rett syndrome (RTT) is caused by mutations in the gene encoding methyl-CpG binding protein 2 (MECP2), an epigenetic regulator of mRNA transcription. Here, we report a test of the hypothesis of shared pathophysiology of RTT and fragile X, another monogenic
Michael S Sidorov et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(41), 12852-12857 (2015-09-30)
A feature of early postnatal neocortical development is a transient peak in signaling via metabotropic glutamate receptor 5 (mGluR5). In visual cortex, this change coincides with increased sensitivity of excitatory synapses to monocular deprivation (MD). However, loss of visual responsiveness
Lothar Lindemann et al.
The Journal of pharmacology and experimental therapeutics, 339(2), 474-486 (2011-08-19)
The metabotropic glutamate receptor 5 (mGlu5) is a glutamate-activated class C G protein-coupled receptor widely expressed in the central nervous system and clinically investigated as a drug target for a range of indications, including depression, Parkinson's disease, and fragile X
Stephanie A Barnes et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 35(45), 15073-15081 (2015-11-13)
Previous studies have hypothesized that diverse genetic causes of intellectual disability (ID) and autism spectrum disorders (ASDs) converge on common cellular pathways. Testing this hypothesis requires detailed phenotypic analyses of animal models with genetic mutations that accurately reflect those seen
Di Tian et al.
Nature neuroscience, 18(2), 182-184 (2015-01-13)
Human chromosome 16p11.2 microdeletion is the most common gene copy number variation in autism, but the synaptic pathophysiology caused by this mutation is largely unknown. Using a mouse with the same genetic deficiency, we found that metabotropic glutamate receptor 5
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