Benzethonium chloride

Chemical properties

White or yellowish-white powder.

Chemical properties

Benzethonium chloride occurs as a white crystalline material with a mild odor and very bitter taste.

Originator

Phemerol,Parke Davis,US,1942

The Uses of Benzethonium chloride

Benzethonium Chloride USP is used as germicide for pharmaceutical and cosmetic products. (USP grade of Hyamine(R) 1622 crystals).

The Uses of Benzethonium chloride

The cationic detergent benzethonium chloride is a well characterized skin irritant and rare sensitizer. Benzethonium chloride has been used in a study to assess the minimum inhibitory concentrations of meticillin-resistant Staphylococcus aureus (MRSA) isolates from Malaysia. It has also been used in a study to prepare biocomposite films from sodium alginate and modified clay.

The Uses of Benzethonium chloride

Hyamine(R) 1622 Crystals is a FDA accepted ingredient for topical applications. It can be used as a bactericide, deodorant, or as a preservative in various applications including those in personal care, veterinary and pharmaceutical.

The Uses of Benzethonium chloride

A synthetic quaternary ammonium salt with surfactant, antiseptic and anti-infective properties. It exhibits microbiocidal activity against a broad range of bacteria, fungi, mold and viruses. It has al so been found to have significant broad-spectrum anticancer activity.

The Uses of Benzethonium chloride

In cosmetics as preservative; cationic surfactant. As disinfectant in dairies and food industries. Clinical reagent for determination of protein in CSF; pharmaceutic aid (preservative).

The Uses of Benzethonium chloride

benzethonium chloride is a preservative that works against algae, bacteria, and fungi. In skin care preparations, it is safe for use at concentrations of 0.5 percent.

What are the applications of Application

Benzethonium chloride is a cationic quaternary ammonium surfactant

definition

ChEBI: A (synthetic) quaternary ammonium salt that is benzyldimethylamine in which the nitrogen is quaternised by a 2-{2-[p-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy}ethyl group, with chloride as the counter-ion. An antiseptic and disinfectant, it i active against a broad spectrum of bacteria, fungi, moulds and viruses.

Production Methods

p-Diisobutylphenol is condensed in the presence of a basic catalyst with β,β'-dichlorodiethyl ether to yield 2-[2-[4-(1,1,3,3-tetramethylbutyl) phenoxy]ethoxy]ethyl chloride. Alkaline dimethylamination then produces the corresponding tertiary amine which, after purification by distillation, is dissolved in a suitable organic solvent and treated with benzyl chloride to precipitate benzethonium chloride.

Manufacturing Process

A mixture of 32 g of p-(α,α,γ,γ-tetramethylbutyl)phenoxyethoxyethyldimethylamine and 12.7 parts of benzyl chloride was warmed in 50 g of benzene for 2 hours. The benzene was then evaporated. The residual viscous mass gave a foamy, soapy solution in water. The original starting materials are p-diisobutylphenol, dichlorodiethyl ether and dimethylamine.

brand name

Microklenz (Carrington); Phemerol Chloride (Parke-Davis).

Therapeutic Function

Topical antiinfective

General Description

Odorless white crystals or powder with a very bitter taste. A 1% solution in water is slightly alkaline to litmus.

Air & Water Reactions

Hygroscopic. May be sensitive to prolonged exposure to air. Water soluble.

Reactivity Profile

Benzethonium chloride is incompatible with strong oxidizing agents Incompatible with soap and anionic detergents. Can react with nitrates. Sensitive to light. Acids cause Benzethonium chloride to precipitate from aqueous solutions of >2% concentration. Stable for two weeks at temperatures up to 140 F, .

Hazard

An oral poison.

Fire Hazard

Flash point data for Benzethonium chloride are not available. Benzethonium chloride is probably combustible.

Flammability and Explosibility

Not classified

Pharmaceutical Applications

Benzethonium chloride is a quaternary ammonium compound used in pharmaceutical formulations as an antimicrobial preservative. Typically, it is used for this purpose in injections, ophthalmic and otic preparations at concentrations 0.01–0.02% w/v. Benzethonium chloride may also be used as a wetting and solubilizing agent, and as a topical disinfectant.
In cosmetics such as deodorants, benzethonium chloride may be used as an antimicrobial preservative in concentrations up to 0.5% w/v.
The physical properties and applications of benzethonium chloride are similar to those of other cationic surfactants such as cetrimide.

Safety Profile

Poison by ingestion,subcutaneous, intraperitoneal, and intravenous routes. Asevere eye irritant. Questionable carcinogen withexperimental neoplastigenic data. Mutation data reported.When heated to decomposition it emits very toxic fumesof Cl ^-

Safety

Benzethonium chloride is readily absorbed and is generally regarded as a toxic substance when administered orally. Ingestion may cause vomiting, collapse, convulsions, and coma. The probable lethal human oral dose is estimated to be 50–500 mg/kg bodyweight.
The topical use of solutions containing greater than 5% w/v benzethonium chloride can cause irritation although benzethonium chloride is not regarded as a sensitizer. The use of 0.5% w/v benzethonium chloride in cosmetics is associated with few adverse effects. A maximum concentration of 0.02% w/v benzethonium chloride is recommended for use in cosmetics used in the eye area and this is also the maximum concentration generally used in pharmaceutical formulations such as injections and ophthalmic preparations.
See also Benzalkonium Chloride.
LD₅₀ (mouse, IP): 15.5 mg/kg
LD₅₀ (mouse, IV): 30 mg/kg
LD₅₀ (mouse, oral): 338 mg/kg
LD₅₀ (rat, IP): 16.5 mg/kg
LD₅₀ (rat, IV): 19 mg/kg
LD₅₀ (rat, oral): 368 mg/kg
LD₅₀ (rat, SC): 119 mg/kg

storage

Benzethonium chloride is stable. Aqueous solutions may be sterilized by autoclaving.
The bulk material should be stored in an airtight container protected from light, in a cool, dry place.

Purification Methods

Crystallise it from boiling acetone after filtering or from CHCl3/pet ether. The precipitate is filtered off, washed with diethyl ether and dried for 24hours in a vacuum desiccator. It is a cationic antiseptic surfactant which forms crystals also from a 1:9 MeOH/Et2O mixture. It foams in water. [Beilstein 12 IV 2187.]

Incompatibilities

Benzethonium chloride is incompatible with soaps and other anionic surfactants and may be precipitated from solutions greater than 2% w/v concentration by the addition of mineral acids and some salt solutions.

Regulatory Status

Included in the FDA Inactive Ingredients Database (IM and IV injections; nasal, ophthalmic and otic preparations). Included in the Canadian List of Acceptable Non-medicinal Ingredients.