Amylmetacresol

Amylmetacresol

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	R02AA20 (WHO)
Legal status
Legal status	OTC
Identifiers
IUPAC name 4-hexylbenzene-1,3-diol
CAS Number	53043-14-4
PubChem CID	14759
ChemSpider	14076 Y
CompTox Dashboard (EPA)	DTXSID8046791
ECHA InfoCard	100.013.722
Chemical and physical data
Formula	C12H18O
Molar mass	178.27 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCC1=C(C=C(C=C1)C)O
InChI InChI=1S/C12H18O/c1-3-4-5-6-11-8-7-10(2)9-12(11)13/h7-9,13H,3-6H2,1-2H3 Y Key:CKGWFZQGEQJZIL-UHFFFAOYSA-N Y
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Amylmetacresol is an antiseptic used to treat infections of the mouth and throat. It is one of two active ingredients in Strepsils / Gorpils lozenges. Boots Group also make a lozenge with this as active ingredient. Amylmetacresol has a RW coefficient of 250.

Definition

Amylmetacresol is 5-methyl-2-pentylphenol. It contains not less than 96.0% and not more than 104.0% of C12H18O.

Characteristics

A clear or almost clear liquid or a solid crystalline mass, colourless or slightly yellow when freshly prepared, which darkens on keeping; odour, characteristic.

Practically insoluble in water ; soluble in ethanol (96%), in ether and in fixed and volatile oils.

Identification

A. The infrared absorption spectrum, Appendix II A, is concordant with the reference spectrum of amylmetacresol (RS 014).

B. The light absorption, Appendix II B, in the range 230 to 350 nm of a 0.004% w/v solution in absolute ethanol containing 2% v/v of 0.1M hydrochloric acid exhibits a maximum at 278 nm and a less well-defined maximum at 286 nm. The absorbance at the maximum at 278 nm is about 0.53.

C. To 5 ml of a 0.5% v/v solution in methanol add 5 ml of bromine water . A yellow precipitate is produced.

D. Freezing point, about 22, Appendix V B.

Weight per ml

0.947 to 0.953 g, Appendix V G.

Related substances

Carry out the method for gas chromatography, Appendix III B, using the following solutions. Solution (1) contains 1% w/v of the substance being examined in chloroform. Solution (2) is the substance being examined.

The chromatographic procedure may be carried out using a glass column (1.8 m 3 mm) packed with acid-washed, silanised diatomaceous support (80 to 100 mesh) coated with 10% w/w of silicone grease (Apiezon L is suitable) and maintained at 180.

In the chromatogram obtained with solution (2) the area of any secondary peak is not greater than 2% and the sum of the areas of any secondary peaks is not greater than 3% by normalisation.

Sulphated ash

Not more than 0.1%, Appendix IX A.

Assay

Dissolve 0.2 g in absolute ethanol containing 2% v/v of 0.1M hydrochloric acid and dilute to 100 ml with the same solvent. Dilute 2 ml of the solution to 100 ml with the same solvent and measure the absorbance of the resulting solution at the maximum at 278 nm, Appendix II B. Calculate the content of C12H18O taking 132 as the value of A(1%, 1 cm) at the maximum at 278 nm.

Storage

Amylmetacresol should be protected from light.

Action and use

Antiseptic. http://www.newdruginfo.com/pharmacopeia/bp2003/British%20Pharmacopoeia%20Volume%20I%20and%20II%5CMonographs%20Medicinal%20and%20Pharmaceutical%20substances%5CA%5CAmylmetacresol.htm

External Links

• The Disinfectant and Antiseptic Properties of Amyl-meta-cresol, nih.gov