QX-222 | CAS# 5369-00-6 | Na+ channel blocker

MedKoo Cat#: 574856 | Name: QX-222

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Description:

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

QX-222 is a sodium channel blocker and lidocane derivative.

Chemical Structure

QX-222

CAS# 5369-00-6

Theoretical Analysis

MedKoo Cat#: 574856

Name: QX-222

CAS#: 5369-00-6

Chemical Formula: C13H21ClN2O

Exact Mass: 256.1342

Molecular Weight: 256.77

Elemental Analysis: C, 60.81; H, 8.24; Cl, 13.81; N, 10.91; O, 6.23

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 375.00	2 Weeks
50mg	USD 850.00	2 Weeks

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Related CAS #

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Synonym

QX-222; QX 222; QX222

IUPAC/Chemical Name

2-[(2,6-Dimethylphenyl)amino]-N,N,N-trimethyl-2-oxoethaniminium chloride

InChi Key

WFKXSWWTOZBDME-UHFFFAOYSA-N

InChi Code

InChI=1S/C13H20N2O.ClH/c1-10-7-6-8-11(2)13(10)14-12(16)9-15(3,4)5;/h6-8H,9H2,1-5H3;1H

SMILES Code

CC1=C(C(=CC=C1)C)NC(=O)C[N+](C)(C)C.[Cl-]

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:

QX-222 is a sodium channel blocker.

In vitro activity:

This study sought to test the hypothesis that general anesthetics block nicotinic acetylcholine receptor channels by binding within the pore of the channel. It used outside-out patches excised from BC3H-1 cells. The binding sites for ether and the aromatic moiety of QX-222 are distinct but close; when ether is bound, the binding of QX-222 is stabilized. However, there is the possibility that ether stabilizes QX-222 by binding to a remote site and allosterically modifying the pore of the channel. Reference: Mol Pharmacol. 1994 Jul;46(1):169-75. https://pubmed.ncbi.nlm.nih.gov/7520126/

In vivo activity:

This study investigated the analgesic properties of a combination of lidocaine and QX-222 and its effects on evoked pain behavior and spontaneous pain behavior in mice. Their results suggest that a combination of lidocaine and QX-222 achieves a long-lasting differential block (sensory selective) and produces divergent effects on evoked and spontaneous pain behaviors in mice. Reference: Biomed Res Int. 2014;2014:628729. https://pubmed.ncbi.nlm.nih.gov/25506595/

Preparing Stock Solutions

The following data is based on the product molecular weight 256.77 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.

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. Dilger JP, Vidal AM. Cooperative interactions between general anesthetics and QX-222 within the pore of the acetylcholine receptor ion channel. Mol Pharmacol. 1994 Jul;46(1):169-75. PMID: 7520126. 2. Hu SP, Zhao JJ, Wang WX, Liu Y, Wu HF, Chen C, Yu L, Gui JB. Coapplication of lidocaine and membrane-impermeable lidocaine derivative QX-222 produces divergent effects on evoked and spontaneous nociceptive behaviors in mice. Biomed Res Int. 2014;2014:628729. doi: 10.1155/2014/628729. Epub 2014 Nov 24. PMID: 25506595; PMCID: PMC4260428. 3. Undrovinas AI, Makielski JC. Blockade of lysophosphatidylcholine-modified cardiac Na channels by a lidocaine derivative QX-222. Am J Physiol. 1996 Aug;271(2 Pt 2):H790-7. doi: 10.1152/ajpheart.1996.271.2.H790. PMID: 8770124.

In vitro protocol:

1. Dilger JP, Vidal AM. Cooperative interactions between general anesthetics and QX-222 within the pore of the acetylcholine receptor ion channel. Mol Pharmacol. 1994 Jul;46(1):169-75. PMID: 7520126.

In vivo protocol:

1. Hu SP, Zhao JJ, Wang WX, Liu Y, Wu HF, Chen C, Yu L, Gui JB. Coapplication of lidocaine and membrane-impermeable lidocaine derivative QX-222 produces divergent effects on evoked and spontaneous nociceptive behaviors in mice. Biomed Res Int. 2014;2014:628729. doi: 10.1155/2014/628729. Epub 2014 Nov 24. PMID: 25506595; PMCID: PMC4260428. 2. Undrovinas AI, Makielski JC. Blockade of lysophosphatidylcholine-modified cardiac Na channels by a lidocaine derivative QX-222. Am J Physiol. 1996 Aug;271(2 Pt 2):H790-7. doi: 10.1152/ajpheart.1996.271.2.H790. PMID: 8770124.

1: Tillman TS, Alvarez FJ, Reinert NJ, Liu C, Wang D, Xu Y, Xiao K, Zhang P, Tang P. Functional Human α7 Nicotinic Acetylcholine Receptor (nAChR) Generated from Escherichia coli. J Biol Chem. 2016 Aug 26;291(35):18276-82. doi: 10.1074/jbc.M116.729970. Epub 2016 Jul 6. PMID: 27385587; PMCID: PMC5000075. 2: Hu SP, Zhao JJ, Wang WX, Liu Y, Wu HF, Chen C, Yu L, Gui JB. Coapplication of lidocaine and membrane-impermeable lidocaine derivative QX-222 produces divergent effects on evoked and spontaneous nociceptive behaviors in mice. Biomed Res Int. 2014;2014:628729. doi: 10.1155/2014/628729. Epub 2014 Nov 24. PMID: 25506595; PMCID: PMC4260428. 3: Dasgupta D, Sikdar SK. Calcium permeable AMPA receptor-dependent long lasting plasticity of intrinsic excitability in fast spiking interneurons of the dentate gyrus decreases inhibition in the granule cell layer. Hippocampus. 2015 Mar;25(3):269-85. doi: 10.1002/hipo.22371. Epub 2014 Oct 30. PMID: 25252134. 4: Lukacs P, Gawali VS, Cervenka R, Ke S, Koenig X, Rubi L, Zarrabi T, Hilber K, Stary-Weinzinger A, Todt H. Exploring the structure of the voltage-gated Na+ channel by an engineered drug access pathway to the receptor site for local anesthetics. J Biol Chem. 2014 Aug 1;289(31):21770-81. doi: 10.1074/jbc.M113.541763. Epub 2014 Jun 19. PMID: 24947510; PMCID: PMC4118135. 5: Shankarappa SA, Sagie I, Tsui JH, Chiang HH, Stefanescu C, Zurakowski D, Kohane DS. Duration and local toxicity of sciatic nerve blockade with coinjected site 1 sodium-channel blockers and quaternary lidocaine derivatives. Reg Anesth Pain Med. 2012 Sep-Oct;37(5):483-9. doi: 10.1097/AAP.0b013e31826125b3. PMID: 22914659; PMCID: PMC3428729. 6: Heiny JA, Kravtsova VV, Mandel F, Radzyukevich TL, Benziane B, Prokofiev AV, Pedersen SE, Chibalin AV, Krivoi II. The nicotinic acetylcholine receptor and the Na,K-ATPase alpha2 isoform interact to regulate membrane electrogenesis in skeletal muscle. J Biol Chem. 2010 Sep 10;285(37):28614-26. doi: 10.1074/jbc.M110.150961. Epub 2010 Jul 1. PMID: 20595385; PMCID: PMC2937887. 7: Sagie I, Kohane DS. Prolonged sensory-selective nerve blockade. Proc Natl Acad Sci U S A. 2010 Feb 23;107(8):3740-5. doi: 10.1073/pnas.0911542107. Epub 2010 Feb 4. PMID: 20133669; PMCID: PMC2840479. 8: Chiara DC, Hong FH, Arevalo E, Husain SS, Miller KW, Forman SA, Cohen JB. Time-resolved photolabeling of the nicotinic acetylcholine receptor by [3H]azietomidate, an open-state inhibitor. Mol Pharmacol. 2009 May;75(5):1084-95. doi: 10.1124/mol.108.054353. Epub 2009 Feb 13. PMID: 19218367; PMCID: PMC2672814. 9: Jansen M, Bali M, Akabas MH. Modular design of Cys-loop ligand-gated ion channels: functional 5-HT3 and GABA rho1 receptors lacking the large cytoplasmic M3M4 loop. J Gen Physiol. 2008 Feb;131(2):137-46. doi: 10.1085/jgp.200709896. PMID: 18227272; PMCID: PMC2213565. 10: Sheets MF, Hanck DA. Outward stabilization of the S4 segments in domains III and IV enhances lidocaine block of sodium channels. J Physiol. 2007 Jul 1;582(Pt 1):317-34. doi: 10.1113/jphysiol.2007.134262. Epub 2007 May 17. PMID: 17510181; PMCID: PMC2075305. 11: Lardin HA, Lee PJ. The voltage dependence of recovery from use-dependent block by QX-222 separates mechanisms for drug egress in the cardiac sodium channel. Biochem Pharmacol. 2006 Apr 28;71(9):1299-1307. doi: 10.1016/j.bcp.2006.01.010. PMID: 16637111. 12: Tsang SY, Tsushima RG, Tomaselli GF, Li RA, Backx PH. A multifunctional aromatic residue in the external pore vestibule of Na+ channels contributes to the local anesthetic receptor. Mol Pharmacol. 2005 Feb;67(2):424-34. doi: 10.1124/mol.67.2.. PMID: 15659774. 13: Chen Q, King T, Vanderah TW, Ossipov MH, Malan TP Jr, Lai J, Porreca F. Differential blockade of nerve injury-induced thermal and tactile hypersensitivity by systemically administered brain-penetrating and peripherally restricted local anesthetics. J Pain. 2004 Jun;5(5):281-9. doi: 10.1016/j.jpain.2004.05.002. PMID: 15219260. 14: Fortune ES, Rose GJ. Voltage-gated Na+ channels enhance the temporal filtering properties of electrosensory neurons in the torus. J Neurophysiol. 2003 Aug;90(2):924-9. doi: 10.1152/jn.00294.2003. Epub 2003 May 15. PMID: 12750421. 15: Li M, Farley RA, Lester HA. Voltage-dependent transient currents of human and rat 5-HT transporters (SERT) are blocked by HEPES and ion channel ligands. FEBS Lett. 2002 Feb 27;513(2-3):247-52. doi: 10.1016/s0014-5793(02)02322-0. PMID: 11904159. 16: Buznikov GA, Bezuglov VV, Nikitina LA, Slotkin TA, Lauder JM. Kholinergicheskaia reguliatsiia razvitiia u zarodysheĭ i lichinok morskikh ezheĭ [Cholinergic regulation of the sea urchin embryonic and larval development]. Ross Fiziol Zh Im I M Sechenova. 2001 Nov;87(11):1548-56. Russian. PMID: 11822358. 17: Gentry CL, Lukas RJ. Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes. J Pharmacol Exp Ther. 2001 Dec;299(3):1038-48. PMID: 11714893. 18: Ortells MO, Barrantes GE. Understanding channel blocking in the nicotinic acetylcholine receptor. Recept Channels. 2001;7(4):273-88. PMID: 11697233. 19: Kutchai H, Geddis LM. Inhibition of the Na,K-ATPase of canine renal medulla by several local anesthetics. Pharmacol Res. 2001 Apr;43(4):399-403. doi: 10.1006/phrs.2001.0803. PMID: 11352545. 20: Sunami A, Glaaser IW, Fozzard HA. Structural and gating changes of the sodium channel induced by mutation of a residue in the upper third of IVS6, creating an external access path for local anesthetics. Mol Pharmacol. 2001 Apr;59(4):684-91. doi: 10.1124/mol.59.4.684. PMID: 11259611.