ChemicalBook > CAS DataBase List > 1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID

1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID

Product Name
1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID
CAS No.
338747-41-4
Chemical Name
1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID
Synonyms
BQCA;Benzyl quinolone carboxylic acid;mAChR,Muscarinic acetylcholine receptor,Inhibitor,inhibit,BQCA;1-(4-Methoxybenzyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic ...;1-(4-Methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID;3-Quinolinecarboxylic acid, 1,4-dihydro-1-[(4-methoxyphenyl)methyl]-4-oxo-
CBNumber
CB6252791
Molecular Formula
C18H15NO4
Formula Weight
309.32
MOL File
Mol file
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1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID Property

Melting point:
210-212 °C
Boiling point:
492.6±45.0 °C(Predicted)
Density 
1.346±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: soluble10mg/mL (clear solution)
form 
powder
pka
0.70±0.20(Predicted)
color 
white to beige
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Safety

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0497
Product name
BQCA
Purity
≥98% (HPLC)
Packaging
10mg
Price
$79.2
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0497
Product name
BQCA
Purity
≥98% (HPLC)
Packaging
50mg
Price
$533
Updated
2024/03/01
Cayman Chemical
Product number
15393
Product name
BQCA
Purity
≥98%
Packaging
5mg
Price
$62
Updated
2024/03/01
Cayman Chemical
Product number
15393
Product name
BQCA
Purity
≥98%
Packaging
10mg
Price
$96
Updated
2024/03/01
Cayman Chemical
Product number
15393
Product name
BQCA
Purity
≥98%
Packaging
25mg
Price
$225
Updated
2024/03/01
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1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID Chemical Properties,Usage,Production

Description

BQCA is a highly selective positive allosteric modulator of the M1 muscarinic acetylcholine receptor (mAChR), as it dose-dependently reduces the concentration of acetylcholine required to activate the M1 receptor. The effective range for potentiation of M1 in cells by BQCA is 0.1 to 100 μM with an inflection point value of 845 nM when 3 nM acetylcholine is used. BQCA displays no potentiation, agonism, or antagonism at other mAChRs at concentrations up to 100 μM. It has excellent brain penetration and increases the firing rate of medial prefrontal cortex neurons in vivo in rats. BQCA prevents scopolamine-induced memory deficits in both contextual fear conditioning and a spontaneous alternation task in mice. It also restores impairment in reversal learning in a mouse model of Alzheimer’s disease and improves memory performance in rats.

Uses

BQCA is a highly selective positive allosteric modulator of the M1 muscarinic acetylcholine receptor (mAChR).

Biochem/physiol Actions

BQCA is a potent muscarinic M1 receptor positive allosteric modulator with selectivity for M1 over M2-M5. It potentiates M1 activity in in vitro and in vivo assays and is orally bioavailable. Muscarinic 1 (M1) receptors are expressed in brain regions responsible for attention and memory, including hippocampus, cortex, and striatum. BQCA binds allosterically to M1 to enhance the binding and efficacy of ACh at the receptor. M1 activation is a proposed mechanism for increasing information processing in disease states, such as Alzheimer′s. M1 agonists are being studied as potential therapeutic agents to treat Alzheimer′s disease and the cognitive and negative symptoms of schizophrenia. BQCA has been shown to improve performance in cognition tasks and increase cerebral blood flow.

in vitro

bqca alone showed no effect on calcium mobilization up to 10 μm but increased ach potency 128.8 ± 20.1-fold at 100 μm. in cho cells stably expressing human m1, bqca (100 μm) activated m1 in the absence of ach to an approximate 50% maximal response. bqca had no effect on m2–m5, indicating 100-fold selectivity [1]. bqca dose-dependently reduced the concentration of acetylcholine required to activate the m1 receptor [1]. the effective range for potentiation of m1 in cells by bqca was 0.1 to 100 μm, with an inflection point value of 845 nm when 3 nm acetylcholine was used [1].

in vivo

in wild-type mice, bqca (15 mg/kg) induced c-fos and arc rna in the cortex, hippocampus, and cerebellum and the arc was also elevated in the striatum. bqca had no effect in m1-/- mice. in wild-type mice, oral administration of 15 mg/kg bqca increased the ratio of phosphoerk (perk) to total erk by 28%. bqca showed excellent brain penetration and increased the firing rate of medial prefrontal cortex neurons in vivo in rats [2].

storage

Store at -20°C

References

[1] ma l, seager m a, wittmann m, et al. selective activation of the m1 muscarinic acetylcholine receptor achieved by allosteric potentiation[j]. proceedings of the national academy of sciences, 2009, 106(37): 15950-15955.
[2] shirey j k, brady a e, jones p j, et al. a selective allosteric potentiator of the m1 muscarinic acetylcholine receptor increases activity of medial prefrontal cortical neurons and restores impairments in reversal learning[j]. journal of neuroscience, 2009, 29(45): 14271-14286.

1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID Suppliers

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View Lastest Price from 1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID manufacturers

Career Henan Chemical Co
Product
1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID 338747-41-4
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
20kg
Release date
2019-12-23

338747-41-4, 1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACIDRelated Search:

(-)-Huperzine A 9-AMINO-1,2,3,4-TETRAHYDRO-ACRIDIN-1-OL, MALEATE 4-DIPHENYLACETOXY-N-METHYLPIPERIDINE METHIODIDE SCEPTRIN 4-(N-[3-CHLOROPHENYL]-CARBAMOYLOXY)-2-BUTYNYLTRIMETHYLAMMONIUM CHLORIDE Galantamine Hydrobromide 6-[5-[(2S)-2-AZETIDINYLMETHOXY]-3-PYRIDINYL]-5-HEXYN-1-OL DIHYDROCHLORIDE 2-(3-PYRIDINYL)PIPERIDINE HYDROCHLORIDE Huperzine A

  • 1-(4-METHOXYBENZYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID
  • 1-(4-Methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  • Benzyl quinolone carboxylic acid
  • BQCA
  • 3-Quinolinecarboxylic acid, 1,4-dihydro-1-[(4-methoxyphenyl)methyl]-4-oxo-
  • 1-(4-Methoxybenzyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic ...
  • mAChR,Muscarinic acetylcholine receptor,Inhibitor,inhibit,BQCA
  • 338747-41-4