Benzethonium chloride

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Benzethonium chloride
Kekulé, skeletal formula of benzethonium chloride
Space-filling model of the component ions benzethonium chloride
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
3D model (
JSmol
)
3898548
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.004.073 Edit this at Wikidata
EC Number
  • 204-479-9
KEGG
MeSH Benzethonium
RTECS number
  • BO7175000
UNII
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) R02AA09 (WHO)
topical
Legal status
Hazards
GHS labelling:
GHS05: Corrosive GHS06: Toxic GHS09: Environmental hazard
Danger
H301, H314, H400
P273, P280, P305+P351+P338, P310
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Benzethonium chloride, also known as hyamine is a synthetic

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

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 (25155-18-4 ) 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

  1. ^ Benzethonium chloride in the Consumer Product Information Database
  2. ^ Tentative final monograph (21CFR 333) Archived May 22, 2014, at the Wayback Machine
  3. ^ Data Sheets
  4. PMID 12595925
    .
  5. ^ "Sciencelab.com, Benzethonium chloride MSDS". Archived from the original on 2018-12-06. Retrieved 2013-06-15.
  6. PMID 11453769
    .
  7. PMID 11606328
    .
  8. ^ "Alfaxan Multidose".
  9. ^ TOXNET
  10. ^ European Pharmacopoeia 5.0 Monographs (PDF). European Pharmacopoeia Commission. p. 2440.[permanent dead link]
  11. ^ "FDA issues final rule on safety and effectiveness of antibacterial soaps". Food & Drug Administration. U.S. Food and Drug Administration. Retrieved February 7, 2017.
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