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L5783

Sigma-Aldrich

Lidocaine N-ethyl bromide

analytical standard, for drug analysis

Synonym(s):

N-(2,6-Dimethylphenylcarbamoylmethyl)triethylammonium bromide, QX-314

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About This Item

Empirical Formula (Hill Notation):
C16H27BrN2O
CAS Number:
21306-56-9
Molecular Weight:
343.30
MDL number:
MFCD00083182
UNSPSC Code:
41116107
PubChem Substance ID:
329817630
NACRES:
NA.24

grade

analytical standard

Quality Level

200

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

format

neat

SMILES string

[Br-].CC[N+](CC)(CC)CC(=O)Nc1c(C)cccc1C

InChI

1S/C16H26N2O.BrH/c1-6-18(7-2,8-3)12-15(19)17-16-13(4)10-9-11-14(16)5;/h9-11H,6-8,12H2,1-5H3;1H

InChI key

DLHMKHREUTXMCH-UHFFFAOYSA-N

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Application

Lidocaine N-ethyl bromide has been used as a standard in studying the demethylation effect of lidocaine N-ethyl bromide on breast cancer cells in vitro using colorimetric assay.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

A quaternary derivative of lidocaine that is not membrane permeable. Blocks both fast Na+-dependent action potentials and voltage-dependent, non-inactivating Na+ conductance.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000378367
0000360732
0000351135
0000340742
0000378367

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Lidocaine and ropivacaine, but not bupivacaine, demethylate deoxyribonucleic acid in breast cancer cells in vitro
Lirk.P, et al.
British Journal of Anaesthesia, 113 (2014)
Kimbria J Blake et al.
Nature communications, 9(1), 37-37 (2018-01-04)
The hallmark of many bacterial infections is pain. The underlying mechanisms of pain during live pathogen invasion are not well understood. Here, we elucidate key molecular mechanisms of pain produced during live methicillin-resistant Staphylococcus aureus (MRSA) infection. We show that
Ricardo E Rivera-Acevedo et al.
Anesthesiology, 114(6), 1425-1434 (2011-04-20)
Transient receptor potential vanilloid subfamily member 1 (TRPV1) channels are important integrators of noxious stimuli with pronounced expression in nociceptive neurons. The experimental local anesthetic, QX-314, a quaternary (i.e., permanently charged) lidocaine derivative, recently has been shown to interact with
D P Roberson et al.
British journal of pharmacology, 164(1), 48-58 (2011-04-05)
We have developed a strategy to target the permanently charged lidocaine derivative lidocaine N-ethyl bromide (QX-314) selectively into nociceptive sensory neurons through the large-pore transient receptor potential cation channel subfamily V (TRPV1) noxious heat detector channel. This involves co-administration of
Hossain Md Zakir et al.
PloS one, 7(9), e44023-e44023 (2012-09-11)
Increased expression of the transient receptor potential vanilloid 1 (TRPV1) channels, following nerve injury, may facilitate the entry of QX-314 into nociceptive neurons in order to achieve effective and selective pain relief. In this study we hypothesized that the level
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