Benzethonium Chloride
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MedKoo CAT#: 531006

CAS#: 121-54-0 (Cl-)

Description: Benzethonium Chloride, also known as Hyamine, is synthetic quaternary ammonium salt that has surfactant, antiseptic, and anti-infective properties. Benzethonium Chloride is commonly used as a topical antimicrobial agent. Benzethonium chloride exhibited concentration-dependent inhibitions of HERG channel currents with IC(50) values of 4nM and 17nM, respectively, which were also voltage-dependent and use-dependent. Benzethonium Chloride shifted the channel activation I-V curves in a hyperpolarized direction for 10-15mV and accelerated channel activation and inactivation processes by 2-fold.


Price and Availability

Size
Price

100g
USD 175
Size
Price

250g
USD 220
Size
Price

Benzethonium Chloride purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 531006
Name: Benzethonium Chloride
CAS#: 121-54-0 (Cl-)
Chemical Formula: C27H42ClNO2
Exact Mass:
Molecular Weight: 448.088
Elemental Analysis: C, 72.37; H, 9.45; Cl, 7.91; N, 3.13; O, 7.14


Related CAS #: 121-54-0 (Cl-)   10172-60-8 (free)  

Synonym: Benzethonium Chloride, Benzethonium Cl, Hyamine, Benzethonium, Solamine, Disilyn

IUPAC/Chemical Name: N-benzyl-N,N-dimethyl-2-(2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)ethoxy)ethan-1-aminium chloride

InChi Key: UREZNYTWGJKWBI-UHFFFAOYSA-M

InChi Code: 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

SMILES Code: CC(C)(C)CC(C1=CC=C(OCCOCC[N+](C)(C)CC2=CC=CC=C2)C=C1)(C)C.[Cl-]


Technical Data

Appearance:
White to off-white crystalline powder.

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Pitaro J, Mood ZA, Daniel SJ. Ototoxicity of aluminum acetate/benzethonium chloride otic solution in the chinchilla animal model. Laryngoscope. 2013 Oct;123(10):2521-5. doi: 10.1002/lary.23904. Epub 2013 Aug 5. PubMed PMID: 23918745.

2: Cižmárik J, Vitková Z, Herdová P, Kodadová A, Vími D. [Formulation of benzethonium chloride into gels]. Ceska Slov Farm. 2014 Jun;63(3):123-6. Czech. PubMed PMID: 25115665.

3: Sürer H, Özgün T, Yilmaz FM, Yilmaz G. The effect of centrifugation on three urine protein assays: benzethonium chloride, benzalkonium chloride and pyrogallol red. Clin Chem Lab Med. 2014 Apr;52(4):e71-3. doi: 10.1515/cclm-2013-0868. PubMed PMID: 24280287.

4: Long Y, Lin Z, Xia M, Zheng W, Li Z. Mechanism of HERG potassium channel inhibition by tetra-n-octylammonium bromide and benzethonium chloride. Toxicol Appl Pharmacol. 2013 Mar 1;267(2):155-66. doi: 10.1016/j.taap.2012.12.021. Epub 2013 Jan 8. PubMed PMID: 23313619; PubMed Central PMCID: PMC4884629.

5: Dao H Jr, Fricker C, Nedorost ST. Sensitization prevalence for benzalkonium chloride and benzethonium chloride. Dermatitis. 2012 Jul-Aug;23(4):162-6. doi: 10.1097/DER.0b013e318260d78d. PubMed PMID: 22828255.

6: Rafsanjany N, Sendker J, Lechtenberg M, Petereit F, Scharf B, Hensel A. Traditionally used medicinal plants against uncomplicated urinary tract infections: Are unusual, flavan-4-ol- and derhamnosylmaysin derivatives responsible for the antiadhesive activity of extracts obtained from stigmata of Zea mays L. against uropathogenic E. coli and Benzethonium chloride as frequent contaminant faking potential antibacterial activities? Fitoterapia. 2015 Sep;105:246-53. doi: 10.1016/j.fitote.2015.07.014. Epub 2015 Jul 22. PubMed PMID: 26210697.

7: Benjamin B, Chris F, Salvador G, Melissa G, Susan N. Visual and confocal microscopic interpretation of patch tests to benzethonium chloride and benzalkonium chloride. Skin Res Technol. 2012 Aug;18(3):272-7. doi: 10.1111/j.1600-0846.2011.00577.x. Epub 2011 Dec 5. PubMed PMID: 22142417.

8: Lukáč M, Mrva M, Garajová M, Mojžišová G, Varinská L, Mojžiš J, Sabol M, Kubincová J, Haragová H, Ondriska F, Devínsky F. Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride. Eur J Med Chem. 2013 Aug;66:46-55. doi: 10.1016/j.ejmech.2013.05.033. Epub 2013 Jun 3. PubMed PMID: 23792315.

9: Mazza R, Mazzette R, McAuliffe O, Jordan K, Fox EM. Differential Gene Expression of Three Gene Targets among Persistent and Nonpersistent Listeria monocytogenes Strains in the Presence or Absence of Benzethonium Chloride. J Food Prot. 2015 Aug;78(8):1569-73. doi: 10.4315/0362-028X.JFP-14-510. PubMed PMID: 26219372.

10: Braun S, Werdehausen R, Gaza N, Hermanns H, Kremer D, Küry P, Hollmann MW, Stevens MF. Benzethonium increases the cytotoxicity of S(+)-ketamine in lymphoma, neuronal, and glial cells. Anesth Analg. 2010 Dec;111(6):1389-93. doi: 10.1213/ANE.0b013e3181f690e4. Epub 2010 Oct 1. PubMed PMID: 20889936.

11: Zaman Z, Speeleveld E, Sneyers L, Desmet K. Inhibition of acetylcholine esterase and choline esterase by benzethonium chloride and avoidance of the benzethonium chloride carry-over inhibitory effect. Eur J Clin Chem Clin Biochem. 1997 Aug;35(8):603-7. PubMed PMID: 9298350.

12: Kopecký F, Kopecká B, Kaclík P. [Properties of benzethonium chloride in micellar solutions and the effect of added sodium chloride]. Ceska Slov Farm. 2006 Jul;55(4):175-80. Czech. PubMed PMID: 16921736.

13: Tsujihama M. [Cytotoxicity of benzethonium chloride on cultured mammalian cells]. Shigaku. 1989 Apr;76(7):1339-51. Japanese. PubMed PMID: 2761957.

14: Lang E, Jilani K, Zelenak C, Pasham V, Bobbala D, Qadri SM, Lang F. Stimulation of suicidal erythrocyte death by benzethonium. Cell Physiol Biochem. 2011;28(2):347-54. doi: 10.1159/000331751. Epub 2011 Aug 16. PubMed PMID: 21865743.

15: Compton FH, Beagrie GS. Inhibitory effect of benzethonium and zinc chloride mouthrinses on human dental plaque and gingivitis. J Clin Periodontol. 1975 Feb;2(1):33-43. PubMed PMID: 1094034.

16: Said J, Walker M, Parsons D, Stapleton P, Beezer AE, Gaisford S. An in vitro test of the efficacy of an anti-biofilm wound dressing. Int J Pharm. 2014 Oct 20;474(1-2):177-81. doi: 10.1016/j.ijpharm.2014.08.034. Epub 2014 Aug 21. PubMed PMID: 25151435.

17: Fukuda S. [Assessment of the carcinogenic hazard of 6 substances used in dental practices. (1) Morphological transformation, DNA damage and sister chromatid exchanges in cultured Syrian hamster embryo cells induced by carbol camphor, eugenol, thymol, EDTA, benzalkonium chloride and benzethonium chloride]. Shigaku. 1987 Feb;74(6):1365-84. Japanese. PubMed PMID: 3146742.

18: Iwamura Y, Hayashi J, Sato T, Sato S, Murakami T, Fujimura T, Sasaki Y, Okada K, Takahashi E, Kikuchi T, Aino M, Noguchi T, Shimazaki Y, Mitani A, Fukuda M. Assessment of oral malodor and tonsillar microbiota after gargling with benzethonium chloride. J Oral Sci. 2016;58(1):83-91. doi: 10.2334/josnusd.58.83. PubMed PMID: 27021544.

19: Yip KW, Mao X, Au PY, Hedley DW, Chow S, Dalili S, Mocanu JD, Bastianutto C, Schimmer A, Liu FF. Benzethonium chloride: a novel anticancer agent identified by using a cell-based small-molecule screen. Clin Cancer Res. 2006 Sep 15;12(18):5557-69. PubMed PMID: 17000693.

20: Avula B, Dentali S, Khan IA. Simultaneous identification and quantification by liquid chromatography of benzethonium chloride, methyl paraben and triclosan in commercial products labeled as grapefruit seed extract. Pharmazie. 2007 Aug;62(8):593-6. PubMed PMID: 17867553.