Merbromin

Merbromin
IUPAC name dibromohydroxymercurifluorescein
Identifiers
CAS number	129-16-8 Y
ChemSpider	10808965 Y
EC number	204-933-6
KEGG	D00861 Y
Jmol-3D images	Image 1
SMILES [Na+].[Na+].[O-]C(=O)c4ccccc4C=1c3cc(Br)c([O-])c([Hg]O)c3O/C/2=C/C(=O)C(/Br)=C\C=1\2
InChI InChI=1S/C20H9Br2O5.Hg.2Na.H2O/c21-13-5-11-17(7-15(13)23)27-18-8-16(24)14(22)6-12(18)19(11)9-3-1-2-4-10(9)20(25)26;;;;/h1-7,24H,(H,25,26);;;;1H2/q;3*+1;/p-3 Y Key: SQFDQLBYJKFDDO-UHFFFAOYSA-K Y InChI=1/C20H9Br2O5.Hg.2Na.H2O/c21-13-5-11-17(7-15(13)23)27-18-8-16(24)14(22)6-12(18)19(11)9-3-1-2-4-10(9)20(25)26;;;;/h1-7,24H,(H,25,26);;;;1H2/q;3*+1;/p-3/rC20H10Br2HgO6.2Na/c21-12-5-10-15(7-14(12)24)29-19-11(6-13(22)18(25)17(19)23-28)16(10)8-3-1-2-4-9(8)20(26)27;;/h1-7,25,28H,(H,26,27);;/q;2*+1/p-2 Key: SQFDQLBYJKFDDO-ISOIBTJNAR
Properties
Molecular formula	C20H8Br2HgNa2O6
Molar mass	750.65 g mol−1
Appearance	dark green solid
Hazards
R-phrases	R26 R27 R28 R33 R50 R53
S-phrases	S13 S28 S36 S45 S60 S61
Main hazards	Toxic, dangerous for the environment
Y (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

Merbromin (marketed as Mercurochrome, Merbromine, Sodium mercurescein, Asceptichrome, Supercrome, Brocasept and Cinfacromin) is a topical antiseptic used for minor cuts and scrapes. Merbromin is an organomercuric disodium salt compound and a fluorescein. It is readily available in most countries but no longer sold in the United States because of its mercury content.

Uses

Merbromin's best-known use is as a topical antiseptic. When applied on a wound, the dark red color stains the skin -- making the detection of any erythema or inflammation, indicative of infection, more difficult. In the United States, its use has been superseded by other agents (e.g., povidone iodine, benzalkonium chloride, chloroxylenol). It is still an important antiseptic, particularly in poorer countries, due to its "unbelievably low cost".^[1] Merbromin is also used as a biological dye to mark tissue margins and as a metal dye in industrial dye penetrant inspection to detect metal fractures.

Mercurochrome

Mercurochrome is the trade name of merbromin. The name is also commonly used for over-the-counter antiseptic solutions consisting of merbromin (typically at 2% concentration) dissolved in either ethyl alcohol (tincture) or water (aqueous).

Its antiseptic qualities were discovered by Johns Hopkins Hospital Dr. Hugh H. Young in 1919.^[2] The chemical soon became popular among parents and doctors for everyday antiseptic uses and it was very commonly used for minor injuries in the schoolyard.

The United States Food and Drug Administration (FDA) removed it from the "generally recognized as safe" and into the "untested" classification to effectively halt its distribution in the United States in 1998 over fears of potential mercury poisoning.^[3][4] It is readily available in most other countries.

Within the United States, products such as Humco Mercuroclear ply on the brand recognition history of Mercurochrome but substitute other ingredients with similar properties (Mercuroclear: "Aqueous solution of benzalkonium chloride and lidocaine hydrochloride"^[5]).

See also

• Thiomersal, also known as Thimerosal or Merthiolate

References

1. ^ Prashant N. Mohite, Ashok M. Bhatnagar (2009). "Mercurochrome 1% as an antiseptic for burns: Economical - but is it efficacious and safe?". The Internet Journal of Surgery 21 (2). ISSN 1528-8242. "Apart from these qualities, still the most important factor for which mercurochrome has remained the favorite of the physicians in the developing countries is its attractive price. The compound is being sold at unbelievably low cost ... the reasons being the low manufacturing cost, longer shelf life, use in diluted form and importantly less propaganda about its medical use." 
2. ^ Isaiah Wilner (2006). The man time forgot: a tale of genius, betrayal, and the creation of Time magazine. HarperCollins. p. 230. ISBN 0060505494. 
3. ^ "Federal Food, Drug, and Cosmetic Act (FD&C Act): Quantitative and Qualitative Analysis of Mercury Compounds in the List". U.S. Food and Drug Administration. 2009-04-30. http://www.fda.gov/RegulatoryInformation/Legislation/FederalFoodDrugandCosmeticActFDCAct/SignificantAmendmentstotheFDCAct/FDAMA/ucm100219.htm. 
4. ^ "What happened to Mercurochrome?". The Straight Dope. 2004-07-23. http://www.straightdope.com/columns/040723.html. 
5. ^ "Mercuroclear MSDS". http://www.humco.com/assets/pdf/1637-Mercuroclear.pdf.