Chloroxylenol

Chloroxylenol, also known as para-chloro-meta-xylenol (PCMX), is an antiseptic and disinfectant which is used for skin disinfection, and together with alcohol for cleaning surgical instruments.[2] It is also used within a number of household disinfectants and wound cleaners.[3] It is thought to act by disrupting microbial cell walls and inactivating cellular enzymes,[4] and is less effective than some other available agents.[5][6] It is available as a liquid.[2]

Chloroxylenol
Names
Preferred IUPAC name
4-Chloro-3,5-dimethylphenol[1]
Other names
  • para-Chloro-meta-xylenol
  • PCMX
  • Dettol
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 1862539
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.631
EC Number
  • 201-793-8
KEGG
MeSH chloroxylenol
PubChem CID
RTECS number
  • ZE6850000
UNII
InChI
  • InChI=1S/C8H9ClO/c1-5-3-7(10)4-6(2)8(5)9/h3-4,10H,1-2H3 N
    Key: OSDLLIBGSJNGJE-UHFFFAOYSA-N N
  • InChI=1/C8H9ClO/c1-5-3-7(10)4-6(2)8(5)9/h3-4,10H,1-2H3
    Key: OSDLLIBGSJNGJE-UHFFFAOYAY
SMILES
  • Cc1cc(O)cc(C)c1Cl
  • CC1=CC(O)=CC(C)=C1Cl
Properties
Chemical formula
 C8H9ClO
Molar mass 156.61 g·mol−1
Melting point 114 to 116 °C (237 to 241 °F; 387 to 389 K)
log P 3.377
Acidity (pKa) 9.76
Basicity (pKb) 4.24
Pharmacology
D08AE05 (WHO)
Hazards
GHS labelling:
Pictograms
Signal word
 Warning
Hazard statements
 H302, H315, H317, H319
Precautionary statements
 P280, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

History

Chloroxylenol was first made in 1927.[7] It is on the World Health Organization's List of Essential Medicines.[8] It is sold in a number of formulations and under a number of brand names, including Dettol.[3][9]

Soon after it was created parachlorometaxylenol was then called PCMX, but this was thought to be a poor name and it was renamed Dettol. Then in 1932 it was marketed in Britain and in India. It had a white on green bottle with a white sword depicted.[10][11]

Properties

Side effects are generally few but can include skin irritation.[2][5] It may be used mixed with water or alcohol.[2] Chloroxylenol is most effective against gram-positive bacteria.[2] It works by disruption of the cell wall and stopping the function of enzymes.[6]

Uses

Chloroxylenol is used in hospitals and households for disinfection and sanitation. It is also commonly used in antibacterial soaps, wound-cleansing applications and household antiseptics.[12] Testing has shown products containing chloroxylenol effective against the SARS-CoV-2 virus[13] and orthopoxviruses.[14]

Side effects

Chloroxylenol is generally slightly to moderately toxic to humans (but highly toxic for the eyes, causing severe eye irritation),[15] is practically non-toxic to birds, and is moderately toxic to freshwater invertebrates. It is highly toxic to fish, cats, and some amphibians and should not be used around them.[16] It is a mild skin irritant and may trigger allergic reactions in some individuals.[17]

Humans

Excessive exposure to chloroxylenol has the potential for causing death. It can be poisonous when swallowed and even when it is unintentionally inhaled. A medical study in Hong Kong which analyzed 177 cases of Dettol ingestion that resulted in emergency department treatment (95% of which were intentional), concluded that "Dettol poisoning resulted in serious complications in 7% of patients, including death."[18]

Animals

Chloroxylenol is toxic to many animals, especially cats.[19] Phenolic compounds are of particular concern because cats are unable to fully metabolize them. A cat may swallow the product by licking its paws after they have come into contact with it.

In Australia, chloroxylenol spray has been shown to be lethal to cane toads, an invasive species that was introduced from Hawaii as a result of bad judgment in 1935. It had been hoped that the amphibian would control the cane beetle but it became highly destructive within the ecosystem. Spraying the disinfectant at close range has been shown to cause rapid death to toads. It is not known whether the toxins are persistent or whether they harm other Australian flora and fauna.

Owing to concerns over potential harm to other Australian wildlife species, the use of chloroxylenol as an agent for pest control was banned in Western Australia by the Department of Environment and Conservation in 2011.[20]

References
  1. CID 2723 from PubChem
  2. World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 324. hdl:10665/44053. ISBN 9789241547659.
  3. Griffiths, Christopher; Barker, Jonathan; Bleiker, Tanya; Chalmers, Robert; Creamer, Daniel (2016-02-29). Rook's Textbook of Dermatology, 4 Volume Set. John Wiley & Sons. p. 128.38. ISBN 9781118441176. Archived from the original on 2017-01-13.
  4. "Skin Antiseptics". StatPearls. StatPearls. 2021.
  5. Digison, MB (2007). "A review of anti-septic agents for pre-operative skin preparation". Plastic Surgical Nursing. 27 (4): 185–9, quiz 190–1. doi:10.1097/01.psn.0000306182.50071.e2. PMID 18165724. S2CID 205427305.
  6. Mahon, Connie R.; Lehman, Donald C.; Manuselis, George Jr. (2014). Textbook of Diagnostic Microbiology (5 ed.). Elsevier Health Sciences. p. 67. ISBN 9780323292627. Archived from the original on 2017-01-13.
  7. Larson, E; Talbot, GH (August 1986). "An approach for selection of health care personnel handwashing agents". Infection Control. 7 (8): 419–424. doi:10.1017/s0195941700064663. PMID 3091524. S2CID 25073768.
  8. World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  9. "Chloroxylenol - brand name list from Drugs.com". www.drugs.com. Archived from the original on 2017-08-28.
  10. Susan Pinto, Viveat (12 March 2015). "40 years ago...And now: Not just germs, Dettol fights rivals unabated". Business Standard India. www.business-standard.com. Archived from the original on 30 March 2017. Retrieved 12 July 2017.
  11. C.S.G. Krishnamacharyulu Rural Marketing: Text and Cases (2010), p. 407, at Google Books
  12. Ascenzi, Joseph M. (1996). "Chloroxylenol: an old-new antimicrobial". Handbook of disinfectants and antiseptics. New York: M. Dekker. ISBN 978-0-8247-9524-5. Archived from the original on 2017-09-23.
  13. Ijaz, Khalid; Whitehead, Kelly; Srinivasan, Vanita; Jones, Chris; Nims, Raymond; Charlesworth, Bruce (2020-05-24). "Microbicidal actives with virucidal efficacy against SARS-CoV-2". American Journal of Infection Control. 48 (8): 972–973. doi:10.1016/j.ajic.2020.05.015. PMC 7246051. PMID 32461067. Retrieved 2021-01-31.
  14. Butcher, W.; Ulaeto, D. (2005). "Contact inactivation of orthopoxviruses by household disinfectants". Journal of Applied Microbiology. Wiley. 99 (2): 279–284. doi:10.1111/j.1365-2672.2005.02601.x. ISSN 1364-5072.
  15. R.E.D Facts, Chloroxylenol, United States Environmental Protection Agency (EPA), September 1994.
  16. Dettol liquid at drugs.com Archived 2015-09-24 at the Wayback Machine
  17. K Verma, Ghanshyam; K Mahajan, Vikram; Shanker, Vinay; Ram Tegta, Geeta; Jindal, Nidhi; Minhas, Samridhi (2011). "Contact depigmentation following irritant contact dermatitis to chloroxylenol (dettol)". Indian J Dermatol Venereol Leprol. 77 (5): 612–4. doi:10.4103/0378-6323.84086. PMID 21860168.
  18. PK Lam; CK Chan; ML Tse; FL Lau (August 2012). "Dettol poisoning and the need for airway intervention" (PDF). Hong Kong Medical Journal. 18 (4): 270–275. PMID 22865169. Archived (PDF) from the original on 2 April 2015. Retrieved 29 March 2015.
  19. "Cats and poisons". icatcare.org. Archived from the original on 2015-08-31.
  20. Narelle Towie (23 May 2009). "Cane toad poison banned". Perth Now. Archived from the original on 15 January 2013. Retrieved 2 February 2013.

Media related to Chloroxylenol at Wikimedia Commons

  • "Chloroxylenol". Drug Information Portal. U.S. National Library of Medicine.
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