Benzethonium chloride

Benzethonium chloride
Preferred IUPAC name N-Benzyl-N,N-dimethyl-2-{2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy}ethanaminium chloride
Systematic name Benzyldimethyl(2-{2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy}ethyl)azanium chloride
Identifiers
CAS number	121-54-0 Y
PubChem	8478
ChemSpider	8165 Y
UNII	PH41D05744 Y
EC number	204-479-9
UN number	2923
KEGG	D01140 Y
MeSH	Benzethonium
ChEBI	CHEBI:31264
ChEMBL	CHEMBL221753 N
RTECS number	BO7175000
ATC code	D08AJ08,R02AA09
Beilstein Reference	3898548
Jmol-3D images	{{#if:[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|Image 1 Image 2
SMILES [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
InChI 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 Y Key: UREZNYTWGJKWBI-UHFFFAOYSA-M Y 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
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
GHS signal word	Danger
GHS hazard statements	H301, H314, H400
GHS precautionary statements	P273, P280, P305+351+338, P310
EU classification	Xn
R-phrases	R22 R37/38 R41
S-phrases	S26 S36/39
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Benzethonium chloride 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]

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 2 year study on rats, there was no evidence of carcinogenic activity.^[4]

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.^[5]

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

In Popular Media

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.^[9]

References