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MedKoo Cat#: 555701 | Name: NBQX free acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

NBQX, also known as FG9202, is an AMPA receptor antagonist. NBQX blocks AMPA receptors in micromolar concentrations (~10–20 µM) and also blocks kainate receptors. In experiments, it is used to counter glutamate excitotoxicity. NBQX was found to have anticonvulsant activity in rodent seizure models. As the disodium salt, NBQX is soluble in water at high concentrations (at least up to 100 mM).

Chemical Structure

NBQX free acid
NBQX free acid
CAS#118876-58-7 (free acid)

Theoretical Analysis

MedKoo Cat#: 555701

Name: NBQX free acid

CAS#: 118876-58-7 (free acid)

Chemical Formula: C12H8N4O6S

Exact Mass: 336.0165

Molecular Weight: 336.28

Elemental Analysis: C, 42.86; H, 2.40; N, 16.66; O, 28.55; S, 9.53

Price and Availability

Size Price Availability Quantity
50mg USD 850.00 2 Weeks
100mg USD 1,550.00 2 Weeks
200mg USD 2,150.00 2 Weeks
500mg USD 2,950.00 2 Weeks
1g USD 3,950.00 2 Weeks
2g USD 6,450.00 2 Weeks
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Related CAS #
118876-58-7 (free acid) 479347-86-9 sodium)
Synonym
NBQX free acid; FG9202; FG-9202; FG 9202;
IUPAC/Chemical Name
6-nitro-2,3-dioxo-1,2,3,4-tetrahydrobenzo[f]quinoxaline-7-sulfonamide
InChi Key
UQNAFPHGVPVTAL-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H8N4O6S/c13-23(21,22)8-3-1-2-5-9(8)7(16(19)20)4-6-10(5)15-12(18)11(17)14-6/h1-4H,(H,14,17)(H,15,18)(H2,13,21,22)
SMILES Code
NS(=O)(C1=C2C(C3=C(C=C2[N+]([O-])=O)NC(C(N3)=O)=O)=CC=C1)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
NBQX (FG9202) is a highly selective and competitive AMPA receptor antagonist.
In vitro activity:
At 50 microM, NBQX significantly attenuated the inhibitory currents induced by the exogenous application of 100 microM glycine as observed using whole-cell recordings from ganglion cells in a slice preparation of the tiger salamander retina. Reference: Neuroreport. 1994 Aug 15;5(13):1558-60. https://pubmed.ncbi.nlm.nih.gov/7529589/
In vivo activity:
Rats were intraperitoneally (i.p.) injected with pentylenetetrazole (PTZ, 50 mg/kg) for 28 consecutive days to establish chronic epilepsy models. Subsequently, NBQX (20 mg/kg, i.p.) was injected for 3 days for the observation of behavioral measurements of epilepsy. The results showed that there are reduction of PNNs and decrease of tenascin-R, aggrecan and neurocan in the medial prefrontal cortex (mPFC) in the rats injected with PTZ. However, NBQX treatment normalized PNNs, tenascin-R, aggrecan and neurocan levels. NBQX was sufficient to decrease seizures through increasing the latency to seizures, decrease the duration of seizure onset, and reduce the scores for the severity of seizures. Reference: PLoS One. 2016 Nov 23;11(11):e0166672. https://pubmed.ncbi.nlm.nih.gov/27880801/
Solvent mg/mL mM
Solubility
DMSO 58.5 174.09
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 336.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Yu W, Miller RF. NBQX suppresses inhibitory glycine currents in retinal ganglion cells. Neuroreport. 1994 Aug 15;5(13):1558-60. doi: 10.1097/00001756-199408150-00004. PMID: 7529589. 2. Chen W, Li YS, Gao J, Lin XY, Li XH. AMPA Receptor Antagonist NBQX Decreased Seizures by Normalization of Perineuronal Nets. PLoS One. 2016 Nov 23;11(11):e0166672. doi: 10.1371/journal.pone.0166672. PMID: 27880801; PMCID: PMC5120819. 3. Gill R, Nordholm L, Lodge D. The neuroprotective actions of 2,3-dihydroxy-6-nitro-7-sulfamoyl-benzo(F)quinoxaline (NBQX) in a rat focal ischaemia model. Brain Res. 1992 May 15;580(1-2):35-43. doi: 10.1016/0006-8993(92)90924-x. PMID: 1504814.
In vitro protocol:
1. Yu W, Miller RF. NBQX suppresses inhibitory glycine currents in retinal ganglion cells. Neuroreport. 1994 Aug 15;5(13):1558-60. doi: 10.1097/00001756-199408150-00004. PMID: 7529589.
In vivo protocol:
1. Chen W, Li YS, Gao J, Lin XY, Li XH. AMPA Receptor Antagonist NBQX Decreased Seizures by Normalization of Perineuronal Nets. PLoS One. 2016 Nov 23;11(11):e0166672. doi: 10.1371/journal.pone.0166672. PMID: 27880801; PMCID: PMC5120819. 2. Gill R, Nordholm L, Lodge D. The neuroprotective actions of 2,3-dihydroxy-6-nitro-7-sulfamoyl-benzo(F)quinoxaline (NBQX) in a rat focal ischaemia model. Brain Res. 1992 May 15;580(1-2):35-43. doi: 10.1016/0006-8993(92)90924-x. PMID: 1504814.
1: Getachew B, Tizabi Y. Both Ketamine and NBQX Attenuate Alcohol-Withdrawal Induced Depression in Male Rats. J Drug Alcohol Res. 2019;8. pii: 236069. doi: 10.4303/jdar/236069. PubMed PMID: 31032138; PubMed Central PMCID: PMC6483102. 2: Dannenhoffer CA, Varlinskaya EI, Spear LP. Effects of AMPA receptor antagonist, NBQX, and extrasynaptic GABA(A) agonist, THIP, on social behavior of adolescent and adult rats. Physiol Behav. 2018 Oct 1;194:212-217. doi: 10.1016/j.physbeh.2018.05.024. Epub 2018 May 22. PubMed PMID: 29800636. 3: Ruda-Kucerova J, Babinska Z, Luptak M, Getachew B, Tizabi Y. Both ketamine and NBQX attenuate alcohol drinking in male Wistar rats. Neurosci Lett. 2018 Feb 14;666:175-180. doi: 10.1016/j.neulet.2017.12.055. Epub 2017 Dec 28. PubMed PMID: 29288725; PubMed Central PMCID: PMC5805612. 4: Zhu H, Zhu R, Deng ZD, Feng YC, Shen HL. [Analgesic effects of ionotropic glutamate receptor antagonists MK-801 and NBQX on collagen-induced arthritis rats]. Beijing Da Xue Xue Bao Yi Xue Ban. 2016 Dec 18;48(6):977-981. Chinese. PubMed PMID: 27987500. 5: Chen W, Li YS, Gao J, Lin XY, Li XH. AMPA Receptor Antagonist NBQX Decreased Seizures by Normalization of Perineuronal Nets. PLoS One. 2016 Nov 23;11(11):e0166672. doi: 10.1371/journal.pone.0166672. eCollection 2016. PubMed PMID: 27880801; PubMed Central PMCID: PMC5120819. 6: Libbey JE, Hanak TJ, Doty DJ, Wilcox KS, Fujinami RS. NBQX, a highly selective competitive antagonist of AMPA and KA ionotropic glutamate receptors, increases seizures and mortality following picornavirus infection. Exp Neurol. 2016 Jun;280:89-96. doi: 10.1016/j.expneurol.2016.04.010. Epub 2016 Apr 9. PubMed PMID: 27072529; PubMed Central PMCID: PMC4860063. 7: Twele F, Bankstahl M, Klein S, Römermann K, Löscher W. The AMPA receptor antagonist NBQX exerts anti-seizure but not antiepileptogenic effects in the intrahippocampal kainate mouse model of mesial temporal lobe epilepsy. Neuropharmacology. 2015 Aug;95:234-42. doi: 10.1016/j.neuropharm.2015.03.014. Epub 2015 Mar 31. PubMed PMID: 25839899. 8: Lippman-Bell JJ, Rakhade SN, Klein PM, Obeid M, Jackson MC, Joseph A, Jensen FE. AMPA receptor antagonist NBQX attenuates later-life epileptic seizures and autistic-like social deficits following neonatal seizures. Epilepsia. 2013 Nov;54(11):1922-32. doi: 10.1111/epi.12378. Epub 2013 Oct 1. PubMed PMID: 24117347; PubMed Central PMCID: PMC4262152. 9: Potschka H, Pekcec A, Weinhold B, Gerardy-Schahn R. Deficiency of neural cell adhesion molecule or its polysialylation modulates pharmacological effects of the AMPA receptor antagonist NBQX. Neuroscience. 2008 Apr 9;152(4):1093-8. doi: 10.1016/j.neuroscience.2007.09.027. Epub 2007 Sep 20. PubMed PMID: 18329813. 10: Zbarska S, Bloedel JR, Bracha V. Cerebellar dysfunction explains the extinction-like abolition of conditioned eyeblinks after NBQX injections in the inferior olive. J Neurosci. 2008 Jan 2;28(1):10-20. doi: 10.1523/JNEUROSCI.3403-07.2008. PubMed PMID: 18171918; PubMed Central PMCID: PMC6671149. 11: Lojková D, Zivanović D, Mares P. Different effects of nonNMDA and NMDA receptor antagonists (NBQX and dizocilpine) on cortical epileptic afterdischarges in rats. Brain Res. 2006 Dec 8;1124(1):167-75. Epub 2006 Oct 27. PubMed PMID: 17070784. 12: Kong LL, Yu LC. It is AMPA receptor, not kainate receptor, that contributes to the NBQX-induced antinociception in the spinal cord of rats. Brain Res. 2006 Jul 19;1100(1):73-7. Epub 2006 Jun 13. PubMed PMID: 16777075. 13: Yoon MH, Bae HB, Choi JI, Jeong SW, Chung SS, Yoo KY, Jeong CY, Kim SJ, Chung ST, Kim CM, An TH. Evaluation of interaction between intrathecal adenosine and MK801 or NBQX in a rat formalin pain model. Pharmacology. 2005 Nov;75(3):157-64. Epub 2005 Sep 15. PubMed PMID: 16166819. 14: Yoon MH, Bae HB, Choi JI. Antinociceptive interactions between intrathecal gabapentin and MK801 or NBQX in rat formalin test. J Korean Med Sci. 2005 Apr;20(2):307-12. PubMed PMID: 15832006; PubMed Central PMCID: PMC2808611. 15: Zahn PK, Pogatzki-Zahn EM, Brennan TJ. Spinal administration of MK-801 and NBQX demonstrates NMDA-independent dorsal horn sensitization in incisional pain. Pain. 2005 Apr;114(3):499-510. PubMed PMID: 15777875. 16: Koh S, Tibayan FD, Simpson JN, Jensen FE. NBQX or topiramate treatment after perinatal hypoxia-induced seizures prevents later increases in seizure-induced neuronal injury. Epilepsia. 2004 Jun;45(6):569-75. PubMed PMID: 15144420. 17: Van Damme P, Leyssen M, Callewaert G, Robberecht W, Van Den Bosch L. The AMPA receptor antagonist NBQX prolongs survival in a transgenic mouse model of amyotrophic lateral sclerosis. Neurosci Lett. 2003 Jun 5;343(2):81-4. PubMed PMID: 12759169. 18: Goda M, Isono M, Fujiki M, Kobayashi H. Both MK801 and NBQX reduce the neuronal damage after impact-acceleration brain injury. J Neurotrauma. 2002 Nov;19(11):1445-56. PubMed PMID: 12490009. 19: Mu X, Azbill RD, Springer JE. NBQX treatment improves mitochondrial function and reduces oxidative events after spinal cord injury. J Neurotrauma. 2002 Aug;19(8):917-27. PubMed PMID: 12225652. 20: Pitsikas N, Rigamonti AE, Cella SG, Muller EE. The non-NMDA receptor antagonist NBQX does not affect rats performance in the object recognition task. Pharmacol Res. 2002 Jan;45(1):43-6. PubMed PMID: 11820860.