Introduction：Basic information about CAS 338747-41-4|BQCA, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | BQCA |
|---|
| CAS Number | 338747-41-4 | Molecular Weight | 309.316 |
|---|
| Density | 1.3±0.1 g/cm3 | Boiling Point | 492.6±45.0 °C at 760 mmHg |
|---|
| Molecular Formula | C18H15NO4 | Melting Point | / |
|---|
| MSDS | ChineseUSA | Flash Point | 251.7±28.7 °C |
|---|
| Symbol |
GHS07 | Signal Word | Warning |
|---|
Names
| Name | 1-[(4-methoxyphenyl)methyl]-4-oxoquinoline-3-carboxylic acid |
|---|
| Synonym | More Synonyms |
|---|
BQCA BiologicalActivity
| Description | BQCA a highly selective allosteric modulator of the M1 mAChR. |
|---|
| Related Catalog | Signaling Pathways >>GPCR/G Protein >>mAChRSignaling Pathways >>Neuronal Signaling >>mAChRResearch Areas >>Neurological Disease |
|---|
| In Vitro | BQCA reduces the concentration of ACh required to activate M1 up to 129-fold with an inflection point value of 845 nM. No potentiation, agonism, or antagonism activity on other mAChRs is observed up to 100 μM[1]. BQCA increases M1 receptor affinity for acetylcholine. The activation of the M1 receptor by BQCA induces a robust inward current and increases spontaneous excitatory postsynaptic currents in medial prefrontal cortex (mPFC) pyramidal cells[2]. |
|---|
| In Vivo | BQCA requires M1 to promote inositol phosphate turnover in primary neurons and to increase c-fos and arc RNA expression and ERK phosphorylation in the brain. BQCA reverses scopolamine-induced memory deficits in contextual fear conditioning, increases blood flow to the cerebral cortex, and increases wakefulness while reducing delta sleep. BQCA induces β-arrestin recruitment to M1, suggesting a role for this signal transduction mechanism in the cholinergic modulation of memory[1]. BQCA increases firing of mPFC pyramidal cells in vivo. BQCA also restores discrimination reversal learning in a transgenic mouse model of Alzheimer's disease[2]. |
|---|
| Kinase Assay | Competition binding reactions used 25 μg human M1 CHO membrane protein, BQCA or vehicle, and 0.15 nM [3H]NMS in 96-well deep-well plates. Binding reactions (30 °C for 2-3 h) are terminated by rapid filtration. Nonspecific binding is determined by adding 10 μM atropine. Filter plates are ished 4×with ice-cold 20 mM HEPES, 100 mM NaCl, and 5 mM MgCl2, pH 7.4 using a 96-well harvester. Plates are dried and radioactivity counted with a microplate scintillation counter[1]. |
|---|
| Animal Admin | Rats: Male Sprague-Dawley rats weighing 225-250 g, are injected i.p. with the micro-suspension (containing 10% tween 80) of BQCA at the dose of 10 mg/kg. The blood and whole brain tissue samples are collected at 0.5, 1, 2, 4 and 8 h. Blood samples are collected through cardiac puncture in EDTA vacutainer tubes. The plasma is separated by centrifugation and stored at −80°C until analysis. The animals are decapitated and the whole brain tissue are removed and immediately frozen on dry ice[2]. Mice: Mice are dosed I.P. with BQCA in 5% beta-cyclodextrin and/or 0.3 mg/kg scopolamine in 0.9% saline 30 min before placement into a chamber for 2 min before 2 tone-footshock pairings (3 kHz, 85 dB tone for 30 s co-terminated with a 0.5 mA, 1 s shock) 2 min apart. Mice are removed to their home cage 30 s after the last pairing. Twenty-four hours later mice are placed into the same chamber and freezing is measured by Video Freeze[1]. |
|---|
| References | [1]. Ma L, et al. Selective activation of the M1 muscarinic acetylcholine receptor achieved by allosteric potentiation. Proc Natl Acad Sci U S A. 2009 Sep 15;106(37):15950-5. [2]. Shirey JK, et al. A selective allosteric potentiator of the M1 muscarinic acetylcholine receptorincreases activity of medial prefrontal cortical neurons and restores impairments in reversal learning. J Neurosci. 2009 Nov 11;29(45):14271-86. |
|---|
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|
| Boiling Point | 492.6±45.0 °C at 760 mmHg |
|---|
| Molecular Formula | C18H15NO4 |
|---|
| Molecular Weight | 309.316 |
|---|
| Flash Point | 251.7±28.7 °C |
|---|
| Exact Mass | 309.100098 |
|---|
| PSA | 68.53000 |
|---|
| LogP | 2.83 |
|---|
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
|---|
| Index of Refraction | 1.649 |
|---|
| InChIKey | BZBBTGCKPRSPGF-UHFFFAOYSA-N |
|---|
| SMILES | COc1ccc(Cn2cc(C(=O)O)c(=O)c3ccccc32)cc1 |
|---|
| Storage condition | 2-8℃ |
|---|
Safety Information
| Symbol |
GHS07 |
|---|
| Signal Word | Warning |
|---|
| Hazard Statements | H302 |
|---|
| RIDADR | NONH for all modes of transport |
|---|
| HS Code | 2933499090 |
|---|
Customs
| HS Code | 2933499090 |
|---|
| Summary | 2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
|---|
Articles1
More Articles
| Detecting quinoxaline-2-carboxylic acid in animal tissues by using sensitive rapid enzyme-linked immunosorbent assay and time-resolved fluoroimmunoassay. Food Chem. 175 , 85-91, (2015) An indirect competitive enzyme-linked immunosorbent assay (ic-ELISA) and time-resolved fluoroimmunoassay (TR-FIA) based on an anti-N-butylquinoxaline-2-carboxamide (BQCA) monoclonal antibody were stan... | |
Synonyms
| bqca |
| 3-Quinolinecarboxylic acid, 1,4-dihydro-1-[(4-methoxyphenyl)methyl]-4-oxo- |
| 1-(4-Methoxybenzyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid |
