Benzethonium chloride

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Benzethonium chloride
Kekulé, skeletal formula of benzethonium chloride
Identifiers
CAS number 121-54-0 YesY
PubChem 8478
ChemSpider 8165 YesY
UNII PH41D05744 YesY
EC number 204-479-9
UN number 2923
KEGG D01140 YesY
MeSH Benzethonium
ChEBI CHEBI:31264 N
ChEMBL CHEMBL221753 N
RTECS number BO7175000
ATC code D08AJ08,R02AA09
Beilstein Reference 3898548
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C27H42ClNO2
Molar mass 448.08 g mol−1
Melting point 163 °C (325 °F; 436 K)
Solubility in water 40 g dm-3 (at 20 °C)
Pharmacology
Routes of
administration
topical
Legal status


OTC(US)

Hazards
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Danger
GHS hazard statements H301, H314, H400
GHS precautionary statements P273, P280, P305+351+338, P310
EU classification Harmful Xn
R-phrases R22 R37/38 R41
S-phrases S26 S36/39
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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[edit]

Antimicrobial[edit]

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.[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, such as in the anaesthetic Ketamine.[7]

Other uses[edit]

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 hydrophillic 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]

In Popular Media[edit]

In Star Trek: Enterprise, benzethonium is used as a painkiller in hospitals on the planet Risa. Ensign Travis Mayweather was given it after a rock climbing accident but he turned out to be allergic.[10]

Benzethonium chloride has also been mentioned in at least two NCIS (TV series) episodes. In "Once a Hero" (Season 4, episode 8), it is mentioned as a preservative for an anthrax vaccine. In "The San Dominick" (Season 12, episode 5), benzethonium chloride along with cetrimide and ammonia are found in a bathtub with a victim to slow the decomposition of the body.


References[edit]

  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.  edit
  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. doi:10.1021/jf010222w.  edit
  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.  edit
  8. ^ TOXNET
  9. ^ European Pharmacopoeia 5.0 Monographs. European Pharmacopoeia Commission. p. 2440. 
  10. ^ Berman, Rick, Brannon,Braga (writers) & Dorn, Michael (director). (May 15, 2002). "Two Days and Two Nights.".Star Trek: Enterprise. Season 1. Episode 25. United Paramount Network.