522-51-0

Basic information

• Product Name: Dequalinium chloride
• Synonyms: 1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM CHLORIDE);1,1'-DECAMETHYLENEBIS(4-AMINOQUINALDINIUM) DICHLORIDE;1,1'-(1,10-DECANEDIYL)BIS(4-AMINO-2-METHYLQUINOLINIUM) DICHLORIDE;DEQUALINIUM CHLORIDE;DEQUALINIUM DICHLORIDE;DECA;1,1’-decamethylenebis(4-amino-quinaldiniudichloride;1,10-decamethylene-bis(4-aminoquinaldiniumchloride)
• CAS NO: 522-51-0
• Molecular Formula: C₃₀H₄₀N₄*2Cl
• Molecular Weight: 527.57
• EINECS: 208-330-9
• Product Categories: Potassium channel;FLUOMIZIN
• Mol File: 522-51-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: ≥300 °C(lit.)
• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: Slightly soluble in water and in ethanol (96 per cent).
• Stability: Stable for 2 years as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 3 months.
• Merck: 13,2930
• CAS DataBase Reference: Dequalinium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Dequalinium chloride(522-51-0)
• EPA Substance Registry System: Dequalinium chloride(522-51-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: VA0700000
• F: 8
• Hazardous Substances Data: 522-51-0(Hazardous Substances Data)

Usage

Description

MitoBloCK-12 (522-51-0) attenuates mitochondrial protein import (4-10 μM). Discovered in a screen of FDA-approved drugs. Blocks translocation of a mutant form of alanine: glyoxylate aminotransferase (AGT) to the mitochondria and restores AGT trafficking to peroxisomes.1?Also reduces oxalate accumulation and thus has potential to treat patients with primary hyperoxaluria 1 who possess mutations in AGT.1?Also displays antimicrobial activity2, inhibits apamin-sensitive K+?channels3?and induces apoptosis by inhibiting XIAP4.

Originator

Dequsan,Sante

Uses

Different sources of media describe the Uses of 522-51-0 differently. You can refer to the following data:
1. Bacteriostat, antiseptic.
2. antiinfectant, antineoplastic
3. Dequalinium Chloride is a quaternary ammonium cation and the active ingredient in various medications including antiseptic and anti-malarial agents.

Definition

ChEBI: An organic chloride salt that is the dichloride salt of dequalinium.

Manufacturing Process

a) 15 g of 4-aminoquinaldine, 15 g of decamethylene diiodide and 200 ml of methyl ethyl ketone were refluxed together for 400 hours. The mixture was allowed to cool, the precipitate filtered off, washed with methyl ethyl ketone, and 1,1'-decamethylenebis(4-aminoquinaldinium chloride) recrystallized from ethyl alcohol containing a little methyl alcohol.b) 160 g of 4-aminoquinaldine, 174 g of decamethylene diiodide and 1,500 ml of methyl isobutyl carbinol were heated together at 120°C for 90 hours. The mixture was allowed to cool, the precipitate filtered off, washed with methyl ethyl ketone and 1,1'-decamethylenebis(4-aminoquinaldinium chloride) recrystallized from ethyl alcohol containing a little methyl alcohol.b) 160 g of 4-aminoquinaldine, 174 g of decamethylene diiodide and 1,500 ml of methyl isobutyl carbinol were heated together at 120°C for 90 hours. The mixture was allowed to cool, the precipitate filtered off, washed with methyl ethyl ketone and 1,1'-decamethylenebis(4-aminoquinaldinium chloride) recrystallized from ethyl alcohol containing a little methyl alcohol.

Brand name

Decabis;Dequacaine;Dequafungan;Dequin;Faringina;Gargilon;Grocreme;Labosept;Maltyl;Phylletten;Soor-gel;Sorot;Tetesept.

Therapeutic Function

Antiseptic, Antifungal

World Health Organization (WHO)

Skin reactions to dequalinium chloride, including necrotic lesions, have been reported. It remains available as a mouth and throat disinfectant in many countries.

References

1) Miyata?et al.?(2014),?Pharmacologic rescue of an enzyme-trafficking defect in primary hyperoxaluria 1; Proc. Natl. Acad. Sci. USA?111?14406 2) Frey Tirri?et al.?(2011),?Antimicrobial topical agents used in the vagina; Curr. Probl. Dermatol.?40?36 3) Castle?et al.?(1993),?Dequalinium: a potent inhibitor of apamin-sensitive K+ channels in hepatocytes and of nicotinic responses in skeletal muscle; Eur. J. Pharmacol.?236?201 4) Orzaez?et al.?(2011),?Characterization of dequalinium as a XIAP antagonist that targets the BIR2 domain; Apoptosis?16?460

InChI:InChI=1/C30H38N4.2ClH/c1-23-21-27(31)25-15-9-11-17-29(25)33(23)19-13-7-5-3-4-6-8-14-20-34-24(2)22-28(32)26-16-10-12-18-30(26)34;;/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3;2*1H

Upstream product

• 4295-06-1 4-chloro-2-methylquinoline 

Relevant articles and documents

Preparation method of dequalinium chloride

The invention relates to a preparation method of dequalinium chloride. The method comprises the following steps: reacting 2-methyl-4-chloroquinoline, used as a starting material, with p-methoxybenzylamine to obtain an amination intermediate II, carrying out a debenzylation reaction on the intermediate to obtain 2-methyl-4-aminoquinaldine, then reacting the 2-methyl-4-aminoquinaldine with 1,10-diiododecane to obtain dequalinium iodide, continuously reacting the dequalinium iodide with hydrochloric acid to obtain dequalinium chloride, and finally recrystallizing with a mixed solvent to obtain refined dequalinium chloride. The preparation method of the dequalinium chloride does not adopt a highly toxic solvent nitrobenzene, and adopts a nontoxic or low-toxicity solvent, and the reaction temperature is reduced in the reaction process, so the method is environmentally friendly, and the reaction conditions are simple; and the refined dequalinium chloride product is prepared through recrystallization using the mixed solvent, so impurities in the dequalinium chloride process are controllable, the yield and purity of the prepared dequalinium chloride are high, the product quality is stable,and the method is suitable for industrial production.

Preparation method of dequalinium chloride and its analogues

The invention provides a preparation method of dequalinium chloride and its analogues and concretely relates to a preparation method of a compound shown in the formula I. The preparation method comprises (1) adding a compound shown in the formula II into a solution containing Cl and water so that the materials undergo a reaction, and (2) adding an oxidizing agent into the product of the step (1) so that the mixture undergoes a reaction, wherein R and R1 are independently selected from H atoms and C1-C6 alkyl and n is 4-20. The preparation method has a high yield.