Benzethonium chloride

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Benzethonium chloride
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Names
Preferred IUPAC name
N-Benzyl-N,N-dimethyl-2-{2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy}ethan-1-aminium chloride
Systematic IUPAC name
Benzyldimethyl(2-{2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy}ethyl)azanium chloride
Identifiers
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3D model (JSmol)
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3898548
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MeSH Benzethonium
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UN number 2923
  • InChI=1S/C27H42NO2.ClH/c1-26(2,3)22-27(4,5)24-13-15-25(16-14-24)30-20-19-29-18-17-28(6,7)21-23-11-9-8-10-12-23;/h8-16H,17-22H2,1-7H3;1H/q+1;/p-1 checkY
    Key: UREZNYTWGJKWBI-UHFFFAOYSA-M checkY
  • InChI=1/C27H42NO2.ClH/c1-26(2,3)22-27(4,5)24-13-15-25(16-14-24)30-20-19-29-18-17-28(6,7)21-23-11-9-8-10-12-23;/h8-16H,17-22H2,1-7H3;1H/q+1;/p-1
    Key: UREZNYTWGJKWBI-REWHXWOFAF
  • [Cl-].CC(C)(C)CC(C)(C)c1ccc(OCCOCC[N+](C)(C)Cc2ccccc2)cc1
  • [Cl-].CC(C)(C)CC(C)(C)C1=CC=C(OCCOCC[N+](C)(C)CC2=CC=CC=C2)C=C1
Properties
C27H42ClNO2
Molar mass 448.09 g·mol−1
Melting point 163 °C (325 °F; 436 K)
40 g dm−3 (at 20 °C)
Pharmacology
D08AJ08 (WHO) Template:ATC
topical
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Hazards
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Benzethonium chloride, also known as hyamine, is a synthetic quaternary ammonium salt. This compound is an odorless white solid, soluble in water. It has surfactant, antiseptic, and anti-infective properties and it is used as a topical antimicrobial agent in first aid antiseptics. It is also found in cosmetics and toiletries such as soap, mouthwashes, anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride is also used in the food industry as a hard surface disinfectant.[1]

Uses

Antimicrobial

Benzethonium chloride exhibits a broad spectrum of microbiocidal activity against bacteria, fungi, mold, and viruses. Independent testing shows that benzethonium chloride is highly effective against such pathogens as methicillin-resistant Staphylococcus aureus, Salmonella, Escherichia coli, Clostridioides difficile, hepatitis B virus, hepatitis C virus, herpes simplex virus (HSV), human immunodeficiency virus (HIV), respiratory syncytial virus (RSV), and norovirus.[citation needed]

The US Food and Drug Administration (FDA) specifies that the safe and effective concentrations for benzethonium chloride are 0.1-0.2% in first aid products.[2] Aqueous solutions of benzethonium chloride are not absorbed through the skin. It is not approved in the US and Europe for use as a food additive. Being a quaternary ammonium salt, it is more toxic than negatively charged surfactants.[3] However, in a two-year study on rats, there was no evidence of carcinogenic activity.[4]

It is available under trade names Salanine, BZT, Diapp, Quatrachlor, Polymine D, Phemithyn, Antiseptol, Disilyn, Phermerol, and others.[5] It is also found in several grapefruit seed extract preparations[6] and can be used as a preservative, as in the anaesthetics ketamine[7] and alfaxalone.[8]

Other uses

In addition to its highly effective antimicrobial activity, benzethonium chloride contains a positively charged nitrogen atom covalently bonded to four carbon atoms. This positive charge attracts it to the skin and hair. This contributes to a soft, powdery after-feel on the skin and hair, as well as long-lasting persistent activity against micro-organisms. Also, this positively charged hydrophilic part of the molecule makes it a cationic detergent.[9]

Benzethonium chloride is also used to titrate the quantity of sodium dodecyl sulfate in a mixture of sodium dodecyl sulfate, sodium chloride and sodium sulfate, using dimidium bromide-sulphan blue as an indicator.[10]

It precipitates as turbidity with anionic polymers in aqueous solution, allowing it to be used to estimate the amount of such polymers present in a sample. This test is used in commercial and industrial water treatment, where polyacrylates, polymaleates, and sulfonated polymers are commonly employed as dispersants.[citation needed]

Methylbenzethonium chloride

A related compound (Template:CAS) is used to treat Leishmania major infections.

Regulation

Some data has suggested that long-term exposure to antibacterial ingredients could contribute to bacterial resistance or hormonal effects. Furthermore, there is little evidence that the use of such ingredients in consumer soaps is actually more effective than plain soap and water. In September 2016, the Food and Drug Administration issued a ban on nineteen consumer antiseptic wash ingredients. A ruling on benzethonium chloride, along with two other similar ingredients, was deferred for a year to allow for more data collection.[11]

References

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  1. ^ Benzethonium chloride in the Consumer Product Information Database
  2. ^ Tentative final monograph (21CFR 333) Script error: No such module "webarchive".
  3. ^ Data Sheets
  4. ^ Page Module:Citation/CS1/styles.css has no content.National Toxicology, Program (1995). "NTP Toxicology and Carcinogenesis Studies of Benzethonium Chloride (CAS No. 121-54-0) in F344/N Rats and B6C3F1 Mice (Dermal Studies)". National Toxicology Program Technical Report Series. 438: 1–220. PMID 12595925.
  5. ^ Page Module:Citation/CS1/styles.css has no content."Sciencelab.com, Benzethonium chloride MSDS". Archived from the original on 2018-12-06. Retrieved 2013-06-15.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Takeoka, G.; Dao, L.; Wong, R. Y.; Lundin, R.; Mahoney, N. (2001). "Identification of Benzethonium Chloride in Commercial Grapefruit Seed Extracts". Journal of Agricultural and Food Chemistry. 49 (7): 3316–20. Bibcode:2001JAFC...49.3316T. doi:10.1021/jf010222w. PMID 11453769.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Coates, K. M.; Flood, P. (2001). "Ketamine and its preservative, benzethonium chloride, both inhibit human recombinant α7 and α4β2 neuronal nicotinic acetylcholine receptors in Xenopusoocytes". British Journal of Pharmacology. 134 (4): 871–9. doi:10.1038/sj.bjp.0704315. PMC 1573008. PMID 11606328.
  8. ^ Page Module:Citation/CS1/styles.css has no content."Alfaxan Multidose".
  9. ^ TOXNET
  10. ^ Page Module:Citation/CS1/styles.css has no content.European Pharmacopoeia 5.0 Monographs (PDF). European Pharmacopoeia Commission. p. 2440.[permanent dead link]
  11. ^ Page Module:Citation/CS1/styles.css has no content."FDA issues final rule on safety and effectiveness of antibacterial soaps". Food & Drug Administration. U.S. Food and Drug Administration. Archived from the original on September 3, 2016. Retrieved February 7, 2017.

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