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U-93631

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U-93631
Names


IUPAC name tert-butyl 4,4-dimethyl-5H-imidazo[1,5-a]quinoxaline-3-carboxylate
Identifiers
CAS Number	152273-12-6
3D model (JSmol)	Interactive image
ChemSpider	171075
PubChem CID	197626
CompTox Dashboard(EPA)	DTXSID90164988
InChI InChI=1S/C17H21N3O2/c1-16(2,3)22-15(21)13-14-17(4,5)19-11-8-6-7-9-12(11)20(14)10-18-13/h6-10,19H,1-5H3 Key: NXBSEJKZKXIYMD-UHFFFAOYSA-N
SMILES CC1(C2=C(N=CN2C3=CC=CC=C3N1)C(=O)OC(C)(C)C)C
Properties
Chemical formula	C₁₇H₂₁N₃O₂
Molar mass	299.374 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

U-93631 is aGABA_A receptor antagonist.

Mechanism of action

The mechanism of action of this compound is not entirely clear, but research shows that it binds to the GABA_A receptor. Its binding site seems to be similar to the one ofpicrotoxin, a potentneurotoxin andconvulsant.

The binding of U-93631 decreases the probability of the chloride channel opening and stabilizes the receptor in an inactivated state.^[1]

References

^Dillon, G. H.; Im, W. B.; Pregenzer, J. F.; Carter, D. B.; Hamilton, B. J. (February 1995)."[4-Dimethyl-3-t-butylcarboxyl-4,5-dihydro (1,5-a) quinoxaline] is a novel ligand to the picrotoxin site on GABAA receptors, and decreases single-channel open probability".The Journal of Pharmacology and Experimental Therapeutics.272 (2):597–603.ISSN 0022-3565.PMID 7531762.

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GABA receptor modulators

GABA_ATooltip γ-Aminobutyric acid A receptor

Positive modulators (abridged; seehere for a full list):α-EMTBL
Alcohols (e.g.,drinking alcohol,2M2B)
Anabolic steroids
Avermectins (e.g.,ivermectin)
Barbiturates (e.g.,phenobarbital)
Benzodiazepines (e.g.,diazepam)
Bromide compounds (e.g.,potassium bromide)
Carbamates (e.g.,meprobamate)
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g.,ergoloid (dihydroergotoxine))
Etazepine
Etifoxine
Fenamates (e.g.,mefenamic acid)
Flavonoids (e.g.,apigenin,hispidulin)
Fluoxetine
Flupirtine
Imidazoles (e.g.,etomidate)
Kava constituents (e.g.,kavain)
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g.,allopregnanolone,cholesterol,THDOC)
Niacin
Niacinamide
Nonbenzodiazepines (e.g.,β-carbolines (e.g.,abecarnil),cyclopyrrolones (e.g.,zopiclone),imidazopyridines (e.g.,zolpidem),pyrazolopyrimidines (e.g.,zaleplon))
Norfluoxetine
Petrichloral
Phenols (e.g.,propofol)
Phenytoin
Piperidinediones (e.g.,glutethimide)
Propanidid
Pyrazolopyridines (e.g.,etazolate)
Quinazolinones (e.g.,methaqualone)
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g.,baicalin)
Stiripentol
Sulfonylalkanes (e.g.,sulfonmethane (sulfonal))
Topiramate
Valerian constituents (e.g.,valerenic acid)
Volatiles/gases (e.g.,chloral hydrate,chloroform,diethyl ether,paraldehyde,sevoflurane)

GABA_A-ρTooltip γ-Aminobutyric acid A-rho receptor

Negative modulators:5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin,picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc

GABA_BTooltip γ-Aminobutyric acid B receptor

Negative modulators:Compound 14

See also: Receptor/signaling modulators; GABA_A receptor positive modulators; GABA metabolism/transport modulators

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