Ethylmercury

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Ethylmercury

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Template:Longitem	Template:Unbulleted list
Template:Longitem	3903035
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EC Number	Template:Unbulleted list
Template:Longitem	323460
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Template:Longitem	C2H5Hg+
Molar mass	229.65 g/mol

Ethylmercury (sometimes ethyl mercury) is a cation composed of an organic CH₃CH₂— species (an ethyl group) bound to a mercury(II) centre, making it a type of organometallic cation, and giving it a chemical formula C₂H₅Hg⁺. The main source of ethylmercury is thimerosal.

Synthesis and structure

File:EthylMercuryPrototypes.svg

Structures of two main types of complexes derived from "ethylmercury". X⁻ = anion, L = neutral Lewis base.

Ethylmercury (C₂H₅Hg⁺) is a substituent of compounds: it occurs as a component of compounds of the formula C₂H₅HgX where X = chloride, thiolate, or another organic group. Most famously X = the mercaptide group of thiosalicylic acid as in thiomersal. In the body, ethylmercury is most commonly encountered as derivatives with a thiolate attached to the mercury. In these compounds, Hg(II) has a linear or sometimes trigonal coordination geometry. Given the comparable electronegativities of mercury and carbon, the mercury-carbon bond is described as covalent.Template:Rp

Toxicity

The toxicity of ethylmercury is well studied. Like methylmercury, ethylmercury distributes to all body tissues, crossing the blood–brain barrier and the placental barrier, and ethylmercury also moves freely throughout the body. Risk assessment for effects on the human nervous system have been made by extrapolating from dose-response relationships for methylmercury. Estimates have suggested that ethylmercury clears from blood with a half-life of 3–7 days in adult humans. In monkeys, it clears from brain tissue with a half-life of 24 days and blood in 7 days.

It is a fungicide but has been banned from use in the U.S. on food grain and even on seeds only used to grow crops.

Public health concerns

Concerns based on extrapolations of the effect of methylmercury caused thimerosal to be removed from U.S. childhood vaccines in 1999, but it remains in use in all multi-dose vaccines and flu shots (though many single use vaccines without thimerosal are available). Researchers have argued that risk assessments based on methylmercury were overly conservative in light of observations that ethylmercury is eliminated from the body and the brain significantly faster than methylmercury. Moreover, the same researchers have argued that inorganic mercury metabolized from ethylmercury, despite its much longer half-life in the brain, is much less toxic than the inorganic mercury produced from mercury vapor, for reasons not yet understood.

See also

• Diethylmercury
• Mercury poisoning

External links

• EPA Organic Mercury TEACH Chemical Summary, 2007.
• EPA Chemistry Dashboard, Ethyl Mercury Ion, 2017.
• ATSDR Toxicological Profile for Mercury, search "Organic Mercury".