2'MeO6MF

Modify Date: 2024-04-02 12:13:50

2'MeO6MF Structure
2'MeO6MF structure
Common Name 2'MeO6MF
CAS Number 89112-85-6 Molecular Weight 266.29100
Density N/A Boiling Point N/A
Molecular Formula C17H14O3 Melting Point N/A
MSDS N/A Flash Point N/A

 Use of 2'MeO6MF


2'MeO6MF is a brain-penetrant positive allosteric modulator at α2β1γ2L and all α1-containing GABAA receptors. 2'MeO6MF also can directly activate α2β2/3 and α2β2/3γ2L GABAA receptors. 2'MeO6MF has anxiolytic and sedative effects. 2'MeO6MF offers neuroprotection and improved functional recovery and dampens the stroke-induced inflammatory response[1][2].

 Names

Name 2-(2-methoxyphenyl)-6-methylchromen-4-one
Synonym More Synonyms

 2'MeO6MF Biological Activity

Description 2'MeO6MF is a brain-penetrant positive allosteric modulator at α2β1γ2L and all α1-containing GABAA receptors. 2'MeO6MF also can directly activate α2β2/3 and α2β2/3γ2L GABAA receptors. 2'MeO6MF has anxiolytic and sedative effects. 2'MeO6MF offers neuroprotection and improved functional recovery and dampens the stroke-induced inflammatory response[1][2].
Related Catalog
Target

GABAA receptor[1]

In Vitro 2'MeO6MF (100-300 µM; 60 min) weakly displaces [3H]-flunitrazepam binding to rat brain synaptosomal membranes by 5-10%. 2'MeO6MF enhances [3H]-muscimol binding to rat brain synaptic membranes in a concentration-dependent manner yielding a mean Emax of 219.8% and apparent EC50=20.8 nM[1]. 2'MeO6MF (1-300 µM) enhances the response elicited by a low concentration of GABA in a concentration-dependent manner at recombinant α1β2γ2L GABAA receptors expressed in XenopusM oocytes. 2'MeO6MF enhances the response elicited by GABA at recombinant α1β1,3γ2L and α1β2 GABAA receptors without any direct activation[1]. 2'MeO6MF (1-10 µM; 60 min) increases tonic inhibitory currents in a concentration-dependent manner in granule cells[2]. 2'MeO6MF (100-1000 µM; 6.5 h) inhibits the LPS-induced increase of NFkB activity in RAWblueTM macrophage cells[2].
In Vivo 2'MeO6MF (1-100 mg/kg; i.p.) displays anxiolytic-like effects in the elevated plus maze and light/dark tests. 2'MeO6MF induces sedative effects at higher doses in the holeboard, actimeter and barbiturate-induced sleep time tests[1]. 2'MeO6MF (30 mg/kg; i.p.) increases tonic currents in layer 2/3 pyramidal neurons of mice after stroke[2]. 2'MeO6MF (0.1-30 mg/kg; i.p.) is neuroprotective and enhances functional recovery after focal cerebral ischaemia in mice[2]. Animal Model: Male Balb-c mice (8-10 weeks, 25-35 g)[1] Dosage: 1, 10, 30, 100 mg/kg Administration: I.p. Result: No overt acute toxicity was observed. Exerted anxiolytic effects at low doses and sedative effects at high doses without myorelaxant effects.
References

[1]. Karim N, et, al. 2'-Methoxy-6-methylflavone: a novel anxiolytic and sedative with subtype selective activating and modulating actions at GABA(A) receptors. Br J Pharmacol. 2012 Feb;165(4):880-96.

[2]. Clarkson AN, et, al. The flavonoid, 2'-methoxy-6-methylflavone, affords neuroprotection following focal cerebral ischaemia. J Cereb Blood Flow Metab. 2019 Jul;39(7):1266-1282.

 Chemical & Physical Properties

Molecular Formula C17H14O3
Molecular Weight 266.29100
Exact Mass 266.09400
PSA 39.44000
LogP 3.77700

 Synthetic Route

~96%

2'MeO6MF Structure

2'MeO6MF

CAS#:89112-85-6

Literature: Kahnberg, Pia; Lager, Erik; Rosenberg, Celia; Schougaard, Jette; Camet, Linda; Sterner, Olov; Nielsen, Elsebet stergaard; Nielsen, Mogens; Liljefors, Tommy Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4188 - 4201

~%

2'MeO6MF Structure

2'MeO6MF

CAS#:89112-85-6

Literature: Mazumdar; Karmakar; Tiwari; Banerjee; Banerji Journal of the Indian Chemical Society, 1990 , vol. 67, # 10 p. 845 - 847

~%

2'MeO6MF Structure

2'MeO6MF

CAS#:89112-85-6

Literature: Kahnberg, Pia; Lager, Erik; Rosenberg, Celia; Schougaard, Jette; Camet, Linda; Sterner, Olov; Nielsen, Elsebet stergaard; Nielsen, Mogens; Liljefors, Tommy Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4188 - 4201

~%

2'MeO6MF Structure

2'MeO6MF

CAS#:89112-85-6

Literature: Kahnberg, Pia; Lager, Erik; Rosenberg, Celia; Schougaard, Jette; Camet, Linda; Sterner, Olov; Nielsen, Elsebet stergaard; Nielsen, Mogens; Liljefors, Tommy Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4188 - 4201

~%

2'MeO6MF Structure

2'MeO6MF

CAS#:89112-85-6

Literature: Kahnberg, Pia; Lager, Erik; Rosenberg, Celia; Schougaard, Jette; Camet, Linda; Sterner, Olov; Nielsen, Elsebet stergaard; Nielsen, Mogens; Liljefors, Tommy Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4188 - 4201

~%

2'MeO6MF Structure

2'MeO6MF

CAS#:89112-85-6

Literature: Mazumdar; Karmakar; Rangachari; Banerjee; Banerji Journal of the Indian Chemical Society, 1990 , vol. 67, # 11 p. 911 - 913

~%

2'MeO6MF Structure

2'MeO6MF

CAS#:89112-85-6

Literature: Baker; Besly Journal of the Chemical Society, 1940 , p. 1103

~%

2'MeO6MF Structure

2'MeO6MF

CAS#:89112-85-6

Literature: Kahnberg, Pia; Lager, Erik; Rosenberg, Celia; Schougaard, Jette; Camet, Linda; Sterner, Olov; Nielsen, Elsebet stergaard; Nielsen, Mogens; Liljefors, Tommy Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4188 - 4201

 Synonyms

4H-1-Benzopyran-4-one,2-(2-methoxyphenyl)-6-methyl
2-(2-methoxyphenyl)-6-methyl-4H-chromen-4-one
2-(2-methoxy-phenyl)-6-methyl-chromen-4-one
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