U-93631

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 their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

U-93631 is a GABA_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 of picrotoxin, a potent neurotoxin and convulsant.

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.

GABA receptor modulators

Ionotropic

GABA_ATooltip γ-Aminobutyric acid A receptor	Agonists: (+)-Catechin Bamaluzole Barbiturates (e.g., phenobarbital) Beta-Alanine BL-1020 DAVA Dihydromuscimol GABA Gabamide GABOB Gaboxadol (THIP) Homotaurine (tramiprosate, 3-APS) Ibotenic acid iso-THAZ iso-THIP Isoguvacine Isomuscimol Isonipecotic acid Kojic amine L-838,417 Lignans (e.g., honokiol) Methylglyoxal Monastrol Muscimol Nefiracetam Neuroactive steroids (e.g., allopregnanolone) Org 20599 PF-6372865 Phenibut Picamilon P4S Progabide Propofol Quisqualamine SL-75102 Taurine TACA TAMP Terpenoids (e.g., borneol) Thiomuscimol Tolgabide ZAPA Positive modulators (abridged; see here 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) Antagonists: Bicuculline Coriamyrtin Dihydrosecurinine Gabazine (SR-95531) Hydrastine Hyenachin (mellitoxin) PHP-501 Pitrazepin Securinine Sinomenine SR-42641 SR-95103 Thiocolchicoside Tutin Negative modulators: 1,3M1B 3M2B 11-Ketoprogesterone 17-Phenylandrostenol α3IA α5IA (LS-193,268) β-CCB β-CCE β-CCM β-CCP β-EMGBL Anabolic steroids Amiloride Anisatin β-Lactams (e.g., penicillins, cephalosporins, carbapenems) Basmisanil Bemegride Bicyclic phosphates (TBPS, TBPO, IPTBO) BIDN Bilobalide Bupropion CHEB Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil) Flavonoids (e.g., amentoflavone, oroxylin A) Flumazenil Fluoroquinolones (e.g., ciprofloxacin) Flurothyl Furosemide Golexanolone Iomazenil (¹²³I) IPTBO Isopregnanolone (sepranolone) L-655,708 Laudanosine Lindane MaxiPost Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Nonsteroidal antiandrogens (e.g., apalutamide, bicalutamide, enzalutamide, flutamide, nilutamide) Oenanthotoxin Pentylenetetrazol (pentetrazol) Phenylsilatrane Picrotoxin (i.e., picrotin, picrotoxinin and dihydropicrotoxinin) Pregnenolone sulfate Propybicyphat PWZ-029 Radequinil Ro 15-4513 Ro 19-4603 RO4882224 RO4938581 Sarmazenil SCS Suritozole TB-21007 TBOB TBPS TCS-1105 Terbequinil TETS Thujone U-93631 Zinc ZK-93426
GABA_A-ρTooltip γ-Aminobutyric acid A-rho receptor	Agonists: BL-1020 CACA CAMP Homohypotaurine GABA GABOB Ibotenic acid Isoguvacine Muscimol N⁴-Chloroacetylcytosine arabinoside Picamilon Progabide TACA TAMP Thiomuscimol Tolgabide Positive modulators: Allopregnanolone Alphaxolone ATHDOC Lanthanides Antagonists: (S)-2-MeGABA (S)-4-ACPBPA (S)-4-ACPCA 2-MeTACA 3-APMPA 4-ACPAM 4-GBA cis-3-ACPBPA CGP-36742 (SGS-742) DAVA Gabazine (SR-95531) Gaboxadol (THIP) I4AA Isonipecotic acid Loreclezole P4MPA P4S SKF-97541 SR-95318 SR-95813 TPMPA trans-3-ACPBPA ZAPA Negative modulators: 5α-Dihydroprogesterone Bilobalide Loreclezole Picrotoxin (picrotin, picrotoxinin) Pregnanolone ROD-188 THDOC Zinc

GABA_ATooltip γ-Aminobutyric acid A receptor

Agonists: (+)-Catechin
Bamaluzole
Barbiturates (e.g., phenobarbital)
Beta-Alanine
BL-1020
DAVA
Dihydromuscimol
GABA
Gabamide
GABOB
Gaboxadol (THIP)
Homotaurine (tramiprosate, 3-APS)
Ibotenic acid
iso-THAZ
iso-THIP
Isoguvacine
Isomuscimol
Isonipecotic acid
Kojic amine
L-838,417
Lignans (e.g., honokiol)
Methylglyoxal
Monastrol
Muscimol
Nefiracetam
Neuroactive steroids (e.g., allopregnanolone)
Org 20599
PF-6372865
Phenibut
Picamilon
P4S
Progabide
Propofol
Quisqualamine
SL-75102
Taurine
TACA
TAMP
Terpenoids (e.g., borneol)
Thiomuscimol
Tolgabide
ZAPA

Positive modulators (abridged; see here 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)

Antagonists: Bicuculline
Coriamyrtin
Dihydrosecurinine
Gabazine (SR-95531)
Hydrastine
Hyenachin (mellitoxin)
PHP-501
Pitrazepin
Securinine
Sinomenine
SR-42641
SR-95103
Thiocolchicoside
Tutin

Negative modulators: 1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
α3IA
α5IA (LS-193,268)
β-CCB
β-CCE
β-CCM
β-CCP
β-EMGBL
Anabolic steroids
Amiloride
Anisatin
β-Lactams (e.g., penicillins, cephalosporins, carbapenems)
Basmisanil
Bemegride
Bicyclic phosphates (TBPS, TBPO, IPTBO)
BIDN
Bilobalide
Bupropion
CHEB
Chlorophenylsilatrane
Cicutoxin
Cloflubicyne
Cyclothiazide
DHEA
DHEA-S
Dieldrin
(+)-DMBB
DMCM
DMPC
EBOB
Etbicyphat
FG-7142 (ZK-31906)
Fiproles (e.g., fipronil)
Flavonoids (e.g., amentoflavone, oroxylin A)
Flumazenil
Fluoroquinolones (e.g., ciprofloxacin)
Flurothyl
Furosemide
Golexanolone
Iomazenil (¹²³I)
IPTBO
Isopregnanolone (sepranolone)
L-655,708
Laudanosine
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Nonsteroidal antiandrogens (e.g., apalutamide, bicalutamide, enzalutamide, flutamide, nilutamide)
Oenanthotoxin
Pentylenetetrazol (pentetrazol)
Phenylsilatrane
Picrotoxin (i.e., picrotin, picrotoxinin and dihydropicrotoxinin)
Pregnenolone sulfate
Propybicyphat
PWZ-029
Radequinil
Ro 15-4513
Ro 19-4603
RO4882224
RO4938581
Sarmazenil
SCS
Suritozole
TB-21007
TBOB
TBPS
TCS-1105
Terbequinil
TETS
Thujone
U-93631
Zinc
ZK-93426

GABA_A-ρTooltip γ-Aminobutyric acid A-rho receptor

Agonists: BL-1020
CACA
CAMP
Homohypotaurine
GABA
GABOB
Ibotenic acid
Isoguvacine
Muscimol
N⁴-Chloroacetylcytosine arabinoside
Picamilon
Progabide
TACA
TAMP
Thiomuscimol
Tolgabide

Antagonists: (S)-2-MeGABA
(S)-4-ACPBPA
(S)-4-ACPCA
2-MeTACA
3-APMPA
4-ACPAM
4-GBA
cis-3-ACPBPA
CGP-36742 (SGS-742)
DAVA
Gabazine (SR-95531)
Gaboxadol (THIP)
I4AA
Isonipecotic acid
Loreclezole
P4MPA
P4S
SKF-97541
SR-95318
SR-95813
TPMPA
trans-3-ACPBPA
ZAPA

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

Metabotropic

GABA_BTooltip γ-Aminobutyric acid B receptor	Agonists: 1,4-Butanediol 3-APPA 4-Fluorophenibut Aceburic acid Arbaclofen Arbaclofen placarbil Baclofen BL-1020 GABA Gabamide GABOB GBL GHB GHBAL GHV GVL Isovaline Lesogaberan Phenibut Picamilon Progabide Sodium oxybate SKF-97,541 SL 75102 Tolgabide Tolibut Positive modulators: ADX-71441 BHF-177 BHFF BSPP CGP-7930 CGP-13501 GS-39783 rac-BHFF KK-92A Antagonists: 2-Hydroxysaclofen CGP-35348 CGP-46381 CGP-52432 CGP-54626 CGP-55845 CGP-64213 DAVA Homotaurine (tramiprosate, 3-APS) Phaclofen Saclofen SCH-50911 SKF-97541 Negative modulators: Compound 14

GABA_BTooltip γ-Aminobutyric acid B receptor