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.[1]
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.[2] 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.[3]: p. 79
Toxicity
The toxicity of ethylmercury is well studied.[4][1] 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.[5] Risk assessment for effects on the human nervous system have been made by extrapolating from dose-response relationships for methylmercury.[1] Estimates have suggested that ethylmercury clears from blood with a half-life of 3–7 days in adult humans; however, this area has not been well studied.[6][7]
Concerns based on extrapolations from methylmercury caused thimerosal to be removed from U.S. childhood vaccines, starting in 1999, but remains in all multi-dose vaccines and flu shots (though many single use vaccines without thimerosal are available[8]). Clarkson has 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.[1] Moreover, Clarkson has 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.[1]
^ abcdeClarkson, Thomas W.; Magos, Laszlo (September 2006). "The toxicology of mercury and its chemical compounds". Critical Reviews in Toxicology. 36 (8): 609–62. doi:10.1080/10408440600845619. PMID 16973445. S2CID 37652857.
^Elschenbroich C (2016). "Main-Group Organometallics [§6.2.3 Organomercury Compounds]". Organometallics (3rd ed.). New York, NY: John Wiley & Sons. pp. 78–86. ISBN978-3-527-80514-3. Retrieved 13 February 2017.
^Counter, S.Allen; Buchanan, Leo H. (2004). "Mercury exposure in children: A review". Toxicology and Applied Pharmacology. 198 (2): 209–230. doi:10.1016/j.taap.2003.11.032. PMID 15236954.
^Clarkson TW, Vyas JB, Ballatori N (October 2007). "Mechanisms of mercury disposition in the body". American Journal of Industrial Medicine. 50 (10): 757–64. doi:10.1002/ajim.20476. PMID 17477364.
^Clifton JC (April 2007). "Mercury exposure and public health". Pediatric Clinics of North America. 54 (2): 237–69, viii. doi:10.1016/j.pcl.2007.02.005. PMID 17448359.[verification needed]
^. WHO. 2012-07-27. Archived from the original on October 19, 2014. Retrieved 2020-05-10.
^Research, Center for Biologics Evaluation and (2019-04-05). "Thimerosal and Vaccines". FDA.
Further reading
Mitchell WJ (2005). "Carbohydrate assimilation by saccharolytic clostridia". Environmental Health Perspectives. 143 (3): 245–50. doi:10.1289/ehp.113-a543. PMC1280369.
DHHS ATSDR, US (March 2013). "Addendum to the Toxicological Profile for Mercury (Alkyl and Dialkyl Compounds)" (PDF). CDC.gov. Retrieved 13 February 2017.
EPA, OA, US (9 September 2015). "Thimerosal in Vaccines". EPA.gov. Retrieved 13 February 2017.
Santos JC, da Silva IM, Braga TC, de Fátima Â, Figueiredo IM, Santos JC (February 2018). "Thimerosal changes protein conformation and increase the rate of fibrillation in physiological conditions: Spectroscopic studies using bovine serum albumin (BSA)". International Journal of Biological Macromolecules. 113: 1032–1040. doi:10.1016/j.ijbiomac.2018.02.116. PMID 29476861.
External links
EPA Organic Mercury TEACH Chemical Summary, 2007.
EPA Chemistry Dashboard, Ethyl Mercury Ion, 2017.
January 26, 2023
ethylmercury, sometimes, ethyl, mercury, cation, composed, organic, ch3ch2, species, ethyl, group, bound, mercury, centre, making, type, organometallic, cation, giving, chemical, formula, c2h5hg, main, source, ethylmercury, thimerosal, identifierscas, number, . 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 1 Ethylmercury IdentifiersCAS Number 21687 36 5 N3D model JSmol Interactive imageBeilstein Reference 3903035ChEBI CHEBI 33204 YChemSpider 5247 YGmelin Reference 323460PubChem CID 7862 chloride66943 bromide5442 cationCompTox Dashboard EPA DTXSID00274466InChI InChI 1S C2H5 Hg c1 2 h1H2 2H3 q 1 YKey MJOUBOKSWBMNGQ UHFFFAOYSA N YSMILES CC Hg PropertiesChemical formula C2H5Hg Molar mass 229 65 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Synthesis and structure 2 Toxicity 3 Public health concerns 4 See also 5 References and notes 6 Further reading 7 External linksSynthesis and structure Edit 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 2 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 3 p 79 Toxicity EditThe toxicity of ethylmercury is well studied 4 1 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 5 Risk assessment for effects on the human nervous system have been made by extrapolating from dose response relationships for methylmercury 1 Estimates have suggested that ethylmercury clears from blood with a half life of 3 7 days in adult humans however this area has not been well studied 6 7 Public health concerns EditMain article Thimerosal and vaccines Concerns based on extrapolations from methylmercury caused thimerosal to be removed from U S childhood vaccines starting in 1999 but remains in all multi dose vaccines and flu shots though many single use vaccines without thimerosal are available 8 Clarkson has 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 1 Moreover Clarkson has 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 1 See also EditDiethylmercury Mercury poisoningReferences and notes Edit a b c d e Clarkson Thomas W Magos Laszlo September 2006 The toxicology of mercury and its chemical compounds Critical Reviews in Toxicology 36 8 609 62 doi 10 1080 10408440600845619 PMID 16973445 S2CID 37652857 Greenwood Norman N Earnshaw Alan 1997 Chemistry of the Elements 2nd ed Butterworth Heinemann ISBN 978 0 08 037941 8 Elschenbroich C 2016 Main Group Organometallics 6 2 3 Organomercury Compounds Organometallics 3rd ed New York NY John Wiley amp Sons pp 78 86 ISBN 978 3 527 80514 3 Retrieved 13 February 2017 Counter S Allen Buchanan Leo H 2004 Mercury exposure in children A review Toxicology and Applied Pharmacology 198 2 209 230 doi 10 1016 j taap 2003 11 032 PMID 15236954 Clarkson TW Vyas JB Ballatori N October 2007 Mechanisms of mercury disposition in the body American Journal of Industrial Medicine 50 10 757 64 doi 10 1002 ajim 20476 PMID 17477364 Clifton JC April 2007 Mercury exposure and public health Pediatric Clinics of North America 54 2 237 69 viii doi 10 1016 j pcl 2007 02 005 PMID 17448359 verification needed Weekly Epidemiological Record vol 87 30 pp 277 288 WHO 2012 07 27 Archived from the original on October 19 2014 Retrieved 2020 05 10 Research Center for Biologics Evaluation and 2019 04 05 Thimerosal and Vaccines FDA Further reading EditMitchell WJ 2005 Carbohydrate assimilation by saccharolytic clostridia Environmental Health Perspectives 143 3 245 50 doi 10 1289 ehp 113 a543 PMC 1280369 DHHS ATSDR US March 2013 Addendum to the Toxicological Profile for Mercury Alkyl and Dialkyl Compounds PDF CDC gov Retrieved 13 February 2017 EPA OA US 9 September 2015 Thimerosal in Vaccines EPA gov Retrieved 13 February 2017 Santos JC da Silva IM Braga TC de Fatima A Figueiredo IM Santos JC February 2018 Thimerosal changes protein conformation and increase the rate of fibrillation in physiological conditions Spectroscopic studies using bovine serum albumin BSA International Journal of Biological Macromolecules 113 1032 1040 doi 10 1016 j ijbiomac 2018 02 116 PMID 29476861 External links EditEPA Organic Mercury TEACH Chemical Summary 2007 EPA Chemistry Dashboard Ethyl Mercury Ion 2017 ATSDR Toxicological Profile for Mercury search Organic Mercury Retrieved from https en wikipedia org w index php title Ethylmercury amp oldid 1086979362, wikipedia, wiki, book, books, library,
