Chloroxylenol

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Chloroxylenol
Kekulé, skeletal formula of chloroxylenol
Names
Systematic IUPAC name
4-chloro-3,5-dimethylphenol[1]
Other names
para-chloro-meta-xylenol (PCMX), Dettol
Identifiers
88-04-0 YesY
3D model (Jmol) Interactive image
Interactive image
1862539
ChEBI CHEBI:34393
ChEMBL ChEMBL398440 N
ChemSpider 21106017 YesY
ECHA InfoCard 100.001.631
EC Number 201-793-8
KEGG D03473 YesY
MeSH chloroxylenol
PubChem 2723
RTECS number ZE6850000
UNII 0F32U78V2Q YesY
Properties
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 pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H302, H315, H317, H319
P280, P305+351+338
Harmful Xn
R-phrases R22, R36/38, R43
S-phrases (S2), S24, S37
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Chloroxylenol, also known as para-chloro-meta-xylenol (PCMX), is an antiseptic and disinfectant which is used for skin disinfection and cleaning surgical instruments.[2] It is also used within a number of household disinfectants and wound cleaner.[3] It is less effective than some other avaliable agents.[4][5] It is available as a liquid.[2]

Side effects are generally few but can include skin irritation.[2][4] It may be used mixed with water or alcohol.[2] Chloroxylenol is is most effective against Gram-positive bacteria.[2] It works by disruption of the cell wall and stopping the function of enzymes.[5]

Chloroxylenol was first made in 1927.[6] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[7] The wholesale cost in the developing world is about 2.00 to 6.20 USD per liter of 5% solution.[8] It is sold in a number of formulations and under a number of brand names including Dettol.[3][9]

Uses[edit]

It is used in hospitals and households for disinfection and sanitation. It is also commonly used in antibacterial soaps, wound-cleansing applications and household antiseptics such as Dettol liquid (to which it contributes its distinctive odor), cream and ointments.[10]

Side effects[edit]

Chloroxylenol is not significantly toxic to humans, is practically non-toxic to birds, and is moderately toxic to freshwater invertebrates. It is highly toxic to fish and cats and should not be used around them.[11] It is a mild skin irritant and may trigger allergic reactions in some individuals.[medical citation needed]

Humans[edit]

Chloroxylenol has the potential for causing lethal toxicity. It is poisonous when swollowed and even when it is unintentionally breathed in.

In a case report, a 42-year-old British man died from Dettol overexposure in May 2007. He had "obsessive cleaning disorder" and used to keep buckets of dettol around his flat with rooms littered with dettol. The autopsy was not able to conclude whether the lethal exposure to Dettol was via ingestion or inhalation.[12] A medical study which analyzed 177 cases of Dettol intoxications via ingestion in Hong Kong concluded that ″Dettol poisoning resulted in serious complications in 7% of patients, including death".[13]

Animals[edit]

Dettol is toxic to many animals, especially cats.[14] Phenols are of particular concern because cats are unable to eliminate the toxins following ingestion. A cat may swallow the product by licking its paws after they have come into contact with it.

In Australia, Dettol 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 Dettol as an agent for pest control was banned in Western Australia by the Department of Environment and Conservation in 2011.[15]

Society and culture[edit]

A number of brand names are avaliable.

The active ingredient in Dettol that confers its antiseptic property is chloroxylenol (C8H9ClO), an aromatic chemical compound. Chloroxylenol comprises 4.8% of Dettol's total admixture,[16] with the rest made up by pine oil, isopropanol, castor oil, soap and water.

References[edit]

  1. ^ CID 2723 from PubChem
  2. ^ a b c d e WHO Model Formulary 2008 (PDF). World Health Organization. 2009. p. 324. ISBN 9789241547659. Retrieved 8 January 2017. 
  3. ^ a b Griffiths, Christopher; Barker, Jonathan; Bleiker, Tanya; Chalmers, Robert; Creamer, Daniel. Rook's Textbook of Dermatology, 4 Volume Set. John Wiley & Sons. p. 128.38. ISBN 9781118441176. 
  4. ^ a b Digison, MB (2007). "A review of anti-septic agents for pre-operative skin preparation.". Plastic surgical nursing : official journal of the American Society of Plastic and Reconstructive Surgical Nurses. 27 (4): 185–9; quiz 190–1. PMID 18165724. 
  5. ^ a b Mahon, Connie R.; Lehman, Donald C.; Jr, George Manuselis (2014). Textbook of Diagnostic Microbiology (5 ed.). Elsevier Health Sciences. p. 67. ISBN 9780323292627. 
  6. ^ Larson, E; Talbot, GH (August 1986). "An approach for selection of health care personnel handwashing agents.". Infection control : IC. 7 (8): 419–24. PMID 3091524. 
  7. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Retrieved 8 December 2016. 
  8. ^ "Chloroxylenol". International Drug Price Indicator Guide. Retrieved 8 December 2016. 
  9. ^ "Chloroxylenol - brand name list from Drugs.com". www.drugs.com. 
  10. ^ Ascenzi, Joseph M. (1996). "Chloroxylenol: an old-new antimicrobial". Handbook of disinfectants and antiseptics. New York: M. Dekker. ISBN 978-0-8247-9524-5. 
  11. ^ Dettol liquid at drugs.com
  12. ^ Lester Haines (29 May 2007). "'Dettol Man' cleans himself to death". The Register. Retrieved 2 February 2013. 
  13. ^ 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. Retrieved 29 March 2015. 
  14. ^ "Cats and poisons". icatcare.org. 
  15. ^ Narelle Towie (23 May 2009). "Cane toad poison banned". Perth Now. Retrieved 2 February 2013. 
  16. ^ "Summary of Product Characteristics / Dettol Liquid" (PDF). MHRA. 22 November 2010. Retrieved 9 November 2014.