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Merck

SML2917

BAY 36-7620

≥98% (HPLC)

Sinónimos:

(3aS,6aS)-5-Methylene-6a-(naphthalen-2-ylmethyl)hexahydro-1H-cyclopenta[c]furan-1-one, (3aS,6aS)-6a-Naphtalen-2-ylmethyl-5-methyliden-hexahydro-cyclopenta[c]furan-1-one, (3aS,6aS)-Hexahydro-5-methylene-6a-(2-naphthalenylmethyl)-1H-cyclopenta[c]furan-1-one, BAY36-7620

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Fórmula empírica (notación de Hill):
C19H18O2
Número CAS:
232605-26-4
Peso molecular:
278.35
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD03700725
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

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InChI

1S/C19H18O2/c1-13-8-17-12-21-18(20)19(17,10-13)11-14-6-7-15-4-2-3-5-16(15)9-14/h2-7,9,17H,1,8,10-12H2/t17-,19+/m1/s1

SMILES string

C=C1C[C@@](CC2=CC3=C(C=C2)C=CC=C3)(C(OC4)=O)[C@]4([H])C1

InChI key

CVIRWLJKDBYYOG-MJGOQNOKSA-N

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -43 to -35°, c = 0.5 in chloroform-d

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Biochem/physiol Actions

BAY36-7620 is a non-competitive, potent and selective metabotropic glutamate mGlu1 receptor (mGluR1) antagonist (IC50 = 160 nM against 0.1 μM (EC50) Glu-stimulated IP) with inverse agonist activity (IC50 = 380 nM with 36-44% basal IP inhibition at 10 μM). BAY36-7620 exhibits neuroprotective (0.01 and 0.03 mg/kg/h, iv. infusion during 4h post acute subdural hematoma induction in rats; triple 0.03-3 mg/kg bolus iv. 0, 2 & 4 h post middle cerebral artery occlusion in rats) and anticonvulsive (MED = 10 mg/kg, iv. immediately after pentylenetetrazole-induced convulsions in mice) efficacy in vivo.
Non-competitive, potent and selective metabotropic glutamate mGlu1 receptor (mGluR1) antagonist with neuroprotective and anticonvulsive efficacy in vivo.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000124928
0000124929
0000120217

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Lauren M Watson et al.
American journal of human genetics, 101(3), 451-458 (2017-09-09)
The metabotropic glutamate receptor 1 (mGluR1) is abundantly expressed in the mammalian central nervous system, where it regulates intracellular calcium homeostasis in response to excitatory signaling. Here, we describe heterozygous dominant mutations in GRM1, which encodes mGluR1, that are associated
U H Schröder et al.
Neuroscience, 157(2), 385-395 (2008-10-04)
In this study we evaluated the effects of the novel, potent non-competitive metabotropic glutamate receptor (mGluR) 1 antagonist (3aS,6aS)-6a-naphthalen-2-ylmethyl-5-methyliden-hexahydro-cyclopental[c]furan-1-on (BAY 36-7620) on different types of synaptic plasticity in the hippocampal cornu ammonis (CA) 1-region and on hippocampus-dependent spatial learning. After
J De Vry et al.
European journal of pharmacology, 428(2), 203-214 (2001-10-25)
This study characterized the neuroprotective and behavioral effects of (3aS,6aS)-6a-naphtalen-2-ylmethyl-5-methyliden-hexahydro-cyclopenta[c]furan-1-on (BAY 36-7620), a novel, selective and systemically active metabotropic glutamate (mGlu)(1) receptor antagonist. In the rat, neuroprotective effects were obtained in the acute subdural hematoma model (efficacy of 40-50% at
Hyun Geun Shim et al.
Journal of neurophysiology, 115(5), 2446-2455 (2016-02-26)
Homeostatic intrinsic plasticity is a cellular mechanism for maintaining a stable neuronal activity level in response to developmental or activity-dependent changes. Type 1 metabotropic glutamate receptor (mGlu1 receptor) has been widely known to monitor neuronal activity, which plays a role
Rachel E Sexton et al.
Scientific reports, 8(1), 16008-16008 (2018-10-31)
Breast cancer remains a major cause of death among women. 15% of these cancers are triple negative breast cancer (TNBC), an aggressive subtype of breast cancer for which no current effective targeted therapy exists. We have previously demonstrated a role
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