Cetylpyridinium chloride

Cetylpyridinium chloride
IUPAC name 1-Hexadecylpyridinium chloride
Other names Acetoquat CPC; Pyrisept EXADECYL-PYRIDINIUM, CHLORIDE
Identifiers
CAS number	123-03-5 Y,  6004-24-6 (monohydrate)
PubChem	31239
ChemSpider	28979 Y
UNII	6BR7T22E2S Y
ChEBI	CHEBI:32915 Y
ChEMBL	CHEMBL34833 Y
ATC code	B05CA01, D08AJ03, D09AA07, R02AA06
Beilstein Reference	3578606
Jmol-3D images	Image 1
SMILES [Cl-].[n+]1(ccccc1)CCCCCCCCCCCCCCCC
InChI InChI=1S/C21H38N.ClH/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-22-20-17-15-18-21-22;/h15,17-18,20-21H,2-14,16,19H2,1H3;1H/q+1;/p-1 Y Key: YMKDRGPMQRFJGP-UHFFFAOYSA-M Y InChI=1/C21H38N.ClH/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-22-20-17-15-18-21-22;/h15,17-18,20-21H,2-14,16,19H2,1H3;1H/q+1;/p-1 Key: YMKDRGPMQRFJGP-REWHXWOFAU
Properties
Molecular formula	C21H38ClN
Molar mass	339.99 g mol−1
Appearance	solid
Melting point	77 °C, 350 K, 171 °F
Hazards
LD50	36 mg/kg (rabbit, iv)[1] 400 mg/kg (rabbit, oral)[1] 6 mg/kg (rat, ip)[1] 30 mg/kg (rat, iv)[1] 200 mg/kg (rat, oral)[1] 250 mg/kg (rat, sc)[1] 10 mg/kg (mouse, ip)[1] 108 mg/kg (mouse, oral)[1]
Y chloride (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cetylpyridinium chloride (CPC) is a cationic quaternary ammonium compound in some types of mouthwashes, toothpastes, lozenges, throat sprays, breath sprays, and nasal sprays. It is an antiseptic that kills bacteria and other microorganisms. It has been shown to be effective in preventing dental plaque and reducing gingivitis.^[2] It has also been used as an ingredient in certain pesticides. However, this ingredient has also been alleged (according to WebMD,^[3] eMedicine,^[4]) to cause brown stains between the teeth and on the surface of teeth similar to chlorhexidine rinse. However, these stains can be easily removed by a dentist during a routine check-up. There have been reports of taste alteration accompanying the use of cetylpyridinium chloride mouthwash.^{[3] [4]}

Synonyms

Cetylpyridinium chloride is present in commercial products such as 1-palmitylpyridinium chloride, C16-alkylpyridinium chloride, 1-hexadecylpyridinium chloride, acetoquat CPC, aktivex, ammonyx CPC, cecure, ceepryn chloride, cepacol, ceprim, cepacol chloride, cetafilm, cetamium, dobendan, halset, ipanol, medilave, mercocet, merothol, pionin B, pristacin, pyrisept, and asept.

Physical and chemical properties

Cetylpyridinium chloride has the molecular formula C₂₁H₃₈NCl and at its pure form is in a solid state at room temperature. It has a melting point of 77 °C when anhydrous or 80–83 °C in its monohydrate form. It is insoluble in acetone, acetic acid, or ethanol. It has a pyridine-like odor. It is combustible. Concentrated solutions are destructive to mucous membranes. It is toxic when swallowed and very toxic when inhaled.

In some products, cetylpyridinium bromide is used instead. Its properties are virtually identical.

Its critical micelle concentration (CMC) is 0.00124M, corresponding to 0.042% in water.

Toxicology and pharmacology

IVN-RAT LD50 30 mg kg^−1[1]

ORL-RBT LD50 400 mg kg^−1[1]

IVN-RBT LD50 36 mg kg^−1[1]

Compendial status

• Food Chemical Codex ^[5]
• United States Pharmacopeia 31 ^{[6][clarification needed]}
• British Pharmacopoeia 1998 ^{[7][clarification needed]}

See also

• Mouthwash
• Oral-B

References

1. ^ ^{a b c d e f g h i j k} Lewis, Richard J. (1996). Sax's Dangerous Properties of Industrial Materials (9th ed.). New York, NY: Van Nostrand Reinhold. p. 691. 
2. ^ Asadoorian, Joanna (2008). "Cetylpyridinium chloride mouth rinse on gingivitis and plaque". Journal of Dental Hygiene. http://findarticles.com/p/articles/mi_hb6368/is_5_82/ai_n31441216/. 
3. ^ ^{a b} "Tooth Discoloration: Causes and Treatments". http://www.webmd.com/content/article/66/79599.htm. 
4. ^ ^{a b} "Tooth Discoloration : Article by Jonathan A Ship, DMD". http://www.emedicine.com/derm/topic646.htm. 
5. ^ The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport01.html. Retrieved 8 July 2009. 
6. ^ USP 31. "<1121> Nomenclature". http://www.usp.org/pdf/EN/USPNF/1121Nomenclature.pdf. Retrieved 8 July 2009. 
7. ^ Therapeutic Goods Administration. "Chemical Substances". http://www.tga.gov.au/docs/pdf/aan/aanchem.pdf. Retrieved 8 July 2009. 

External links

• Material Safety Data Sheet
• Chemical Information
• An in vitro evaluation of the availability of cetylpyridinium chloride and chlorhexidine in some commercially available mouthrinse products by S. Sheen and M. Addy in British Dental Journal
• Amazon Reviews