Cetylpyridinium chloride

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Cetylpyridinium chloride
IUPAC name	1-Hexadecylpyridinium chloride
Other names	Acetoquat CPC; Pyrisept EXADECYL-PYRIDINIUM, CHLORIDE
Identifiers
CAS number	123-03-5 Y
PubChem	31239
SMILES	[Cl-].[n+]1(ccccc1)CCCCCCCCCCCCCCCC
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
InChI key	YMKDRGPMQRFJGP-REWHXWOFAU
ChemSpider ID	28979
Properties
Molecular formula	C21H38NCl
Molar mass	339.99 g/mol
Melting point	77 °C, 350 K, 171 °F
Y (what is this?)  (verify) 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, anti-sore 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.^{[citation needed]} It has also been used as an ingredient in certain pesticides. However, this ingredient has also been alleged (according to WebMD,^[1] eMedicine,^[2]) to cause brown stains between the teeth similar to Chlorhexidine rinse. Flossing your teeth regularly and with good technique will prevent this type of extrinsic staining.

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.

The CAS number for the monohydrate is [6004-24-6].

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

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

Toxicology and pharmacology

IPR-RAT LDLO 15 mg kg^{−1[citation needed]}

IVN-RAT LD50 30 mg kg^{−1[citation needed]}

ORL-MUS LD50 108 mg kg^{−1[citation needed]}

ORL-RBT LD50 400 mg kg^{−1[citation needed]}

IVN-RBT LD50 36 mg kg^{−1[citation needed]}

This section requires expansion.

Compendial status

• Food Chemical Codex ^[3]
• United States Pharmacopeia 31 ^{[4][clarification needed]}
• British Pharmacopoeia 1998 ^{[5][clarification needed]}

This section requires expansion.

See also

• Mouthwash
• Oral-B

References

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