Benzethonium chloride

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}ethanaminium chloride
Systematic IUPAC name
Benzyldimethyl(2-{2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy}ethyl)azanium chloride
Identifiers
121-54-0 YesY
3898548
ChEBI CHEBI:31264 N
ChEMBL ChEMBL221753 N
ChemSpider 8165 YesY
EC Number 204-479-9
Jmol interactive 3D Image
Image
KEGG D01140 YesY
MeSH Benzethonium
PubChem 8478
RTECS number BO7175000
UNII PH41D05744 YesY
UN number 2923
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
ATC code D08AJ08
R02AA09
Legal status
topical
Hazards
GHS pictograms
GHS signal word Danger
H301, H314, H400
P273, P280, P305+351+338, P310
Xn
R-phrases R22 R37/38 R41
S-phrases S26 S36/39
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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 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, Clostridium difficile, hepatitis B virus, hepatitis C virus, herpes simplex virus (HSV), human immunodeficiency virus (HIV), respiratory syncytial virus (RSV), and norovirus.

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, such as in the anaesthetic Ketamine.[7]

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 afterfeel on the skin and hair, as well as long-lasting persistent activity against microorganisms. Also, this positively charged hydrophilic part of the molecule makes it a cationic detergent.[8]

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.[9]

References

  1. ↑ Record in the Household Products Database of NLM
  2. ↑ Tentative final monograph (21CFR 333)
  3. ↑ Data Sheets
  4. ↑ 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. ↑ Sciencelab.com, Benzethonium chloride MSDS
  6. ↑ 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. doi:10.1021/jf010222w. PMID 11453769.
  7. ↑ 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. doi:10.1038/sj.bjp.0704315. PMID 11606328.
  8. ↑ TOXNET
  9. ↑ European Pharmacopoeia 5.0 Monographs (PDF). European Pharmacopoeia Commission. p. 2440.
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