Nitromersol

Nitromersol (metaphen) is a mercury-containing organic compound that is primarily used as an antiseptic and disinfectant. It is a brown-yellow solid that has no odor or taste, does not irritate the skin or mucous membranes, and has no impact on rubber or metallic instruments, including surgical and dental tools.[1]

Nitromersol
Names
IUPAC name
5-Methyl-2-nitro-7-oxa-8-mercurabicyclo[4.2.0]octa-1(6),2,4-triene
Other names
Metaphen; 6-Methyl-3-nitrobenzoxamercurete; 4-Nitro-5-hydroxymercuriorthocresol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.648
PubChem CID
UNII
InChI
  • InChI=1S/C7H6NO3.Hg/c1-5-2-3-6(8(10)11)4-7(5)9;/h2-3,9H,1H3;/q;+1/p-1
    Key: UEHLXXJAWYWUGI-UHFFFAOYSA-M
  • InChI=1/C7H6NO3.Hg/c1-5-2-3-6(8(10)11)4-7(5)9;/h2-3,9H,1H3;/q;+1/p-1/rC7H5HgNO3/c1-4-2-3-5(9(10)11)6-7(4)12-8-6/h2-3H,1H3
    Key: UEHLXXJAWYWUGI-ITKDQSLKAT
SMILES
  • Cc1ccc(c2[Hg]Oc12)[N+]([O-])=O
Properties
Chemical formula
 C7H5HgNO3
Molar mass 351.713 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 moderately toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

This compound is a confirmed animal carcinogen. It can emit toxic fumes of NOx and mercury vapor when heated.[2] In 1998, use of nitromersol (and other mercury-containing products) as OTC first-aid antiseptics and products for diaper rash and vaginal contraceptives was disallowed by the FDA.[3] Nitromersol can cause hypersensitivity reactions.[4]

It is still in use as a preservative for vaccines and antitoxins.

See also
  • Thiomersal – Organomercury antiseptic and antifungal agent
  • Phenylmercuric nitrate - an organomercury compound with powerful antiseptic and antifungal effects

References
  1. Hospital formulary and compendium of useful information. Berkeley, California: University of California Press. 1941. p. 113. Retrieved 2011-04-08.
  2. Lewis, Richard J. (2008). Hazardous chemicals desk reference. Wiley-Interscience. p. 1018. ISBN 978-0-470-18024-2. Retrieved 2011-04-08.
  3. Remington: the science and practice of pharmacy. Medicine Series. Vol. 1 (21st ed.). Lippincott Williams & Wilkins. 2005. p. 369. ISBN 0-7817-4673-6.
  4. Trevor, Anthony J.; Katzung, Bertram G.; Masters, Susan B. (2007). Katzung & Trevor's pharmacology: examination & board review. Lange Basic Science (8th ed.). McGraw-Hill Professional. p. 420. ISBN 978-0-07-148869-3.
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