From Wikipedia, the free encyclopedia
GABAA PAM, flavonoid
6-Methylapigenin
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Names
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IUPAC name
5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-methylchromen-4-one
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Identifiers
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InChI=1S/C16H12O5/c1-8-11(18)6-14-15(16(8)20)12(19)7-13(21-14)9-2-4-10(17)5-3-9/h2-7,17-18,20H,1H3
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CC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC=C(C=C3)O)O
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Properties
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C16H12O5
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Molar mass
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284.267 g·mol−1
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
6-Methylapigenin is a naturally occurring
flavonoid and a derivative of
apigenin. It has activity at
GABAA receptors as a positive modulator.
Natural occurrence
6-Methylapigenin can be found in multiple plants, such as
Valeriana officinalis,
Valeriana jatamansi, and
Picea neoveitchii.
[1]
Biological activity
6-Methylapigenin binds to the
GABAA receptor on the
benzodiazepine binding site. This compound possesses
anxiolytic effects. In a mouse model, it is also able to potentiate sleep induced by
hesperidin, another
flavonoid.
[2]
[3] However, since it does not have the chemical structure of
benzodiazepines, it can therefore be classed as a
nonbenzodiazepine.
References
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^ PubChem.
"6-Methylapigenin". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-02-04.
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^ Fernández, Sebastián P.; Wasowski, Cristina; Paladini, Alejandro C.; Marder, Mariel (2005-04-11).
"Synergistic interaction between hesperidin, a natural flavonoid, and diazepam". European Journal of Pharmacology. 512 (2–3): 189–198.
doi:
10.1016/j.ejphar.2005.02.039.
ISSN
0014-2999.
PMID
15840404.
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^ Marder, Mariel; Viola, Haydeé; Wasowski, Cristina; Fernández, Sebastián; Medina, Jorge H.; Paladini, Alejandro C. (2003).
"6-methylapigenin and hesperidin: new valeriana flavonoids with activity on the CNS". Pharmacology, Biochemistry, and Behavior. 75 (3): 537–545.
doi:
10.1016/s0091-3057(03)00121-7.
ISSN
0091-3057.
PMID
12895671.
S2CID
37559366.
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Alcohols | |
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Barbiturates | |
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Benzodiazepines | |
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Carbamates | |
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Flavonoids | |
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Imidazoles | |
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Kava constituents | |
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Monoureides | |
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Neuroactive steroids | |
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Nonbenzodiazepines | |
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Phenols | |
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Piperidinediones | |
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Pyrazolopyridines | |
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Quinazolinones | |
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Volatiles/
gases | |
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Others/unsorted |
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3-Hydroxybutanal
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α-EMTBL
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AA-29504
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Alogabat
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Avermectins (e.g.,
ivermectin)
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Bromide compounds (e.g.,
lithium bromide,
potassium bromide,
sodium bromide)
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Carbamazepine
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Chloralose
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Chlormezanone
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Clomethiazole
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Darigabat
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DEABL
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Deuterated etifoxine
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Dihydroergolines (e.g.,
dihydroergocryptine,
dihydroergosine,
dihydroergotamine,
ergoloid (dihydroergotoxine))
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DS2
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Efavirenz
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Etazepine
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Etifoxine
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Fenamates (e.g.,
flufenamic acid,
mefenamic acid,
niflumic acid,
tolfenamic acid)
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Fluoxetine
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Flupirtine
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Hopantenic acid
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KRM-II-81
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Lanthanum
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Lavender oil
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Lignans (e.g.,
4-O-methylhonokiol,
honokiol,
magnolol,
obovatol)
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Loreclezole
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Menthyl isovalerate (validolum)
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Monastrol
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Niacin
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Niacinamide
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Org 25,435
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Phenytoin
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Propanidid
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Retigabine (ezogabine)
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Safranal
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Seproxetine
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Stiripentol
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Sulfonylalkanes (e.g.,
sulfonmethane (sulfonal),
tetronal,
trional)
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Terpenoids (e.g.,
borneol)
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Topiramate
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Valerian constituents (e.g.,
isovaleric acid,
isovaleramide,
valerenic acid,
valerenol)
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