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Tribromoethanol

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Tribromoethanol
Clinical data
Trade namesAvertin
Other namesTribromoethyl alcohol
Identifiers
  • 2,2,2-Tribromoethanol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.000.822 Edit this at Wikidata
Chemical and physical data
FormulaC2H3Br3O
Molar mass282.757 g·mol−1
3D model (JSmol)
Melting point73–79 °C (163–174 °F) [1]
Boiling point92–93 °C (198–199 °F) at 10 mmHg[1]
  • C(C(Br)(Br)Br)O
  • InChI=1S/C2H3Br3O/c3-2(4,5)1-6/h6H,1H2
  • Key:YFDSDPIBEUFTMI-UHFFFAOYSA-N

Tribromoethanol is a sedative. It is used to anesthetize laboratory animals, particularly rodents, before surgery.[2] As a solution in tert-amyl alcohol, it has the brand name Avertin.[3] Tribromoethanol causes rapid and deep anesthesia followed by rapid and full postoperative recovery.[4]

Tribromoethanol was widely used as a general anesthetic in humans in the first half of the twentieth century.[5] Electrophysiology studies showed that tribromoethanol acts as a positive allosteric modulator of the inhibitory GABAA and glycine receptors, a mechanism similar to that seen with the related compound 2,2,2-trichloroethanol.[6] Bromal hydrate (2,2,2-tribromoethanol-1,1-diol), a compound also recognized to produce general anesthesia in animals, is metabolized to tribromoethanol.[7]

See also

References

  1. ^ a b "2,2,2-Tribromoethanol". Sigma-Aldrich.
  2. ^ "Tribromoethanol (Avertin)". Cold Spring Harbor Protocols. Cold Spring Harbor Laboratory.
  3. ^ "Guidelines for the Use of Tribromoethanol/Avertin Anesthesia" (PDF). National Cancer Institute.
  4. ^ "Tribromoethanol (Avertin) as an anaesthetic in mice" (PDF). Laboratory Animals. 33: 192–193. 1999.
  5. ^ G Edwards (1945). "Tribromethyl alcohol (avertin, bromethol), 1928-1945". Proceedings of the Royal Society of Medicine. 39: 71–76. PMID 21010258.
  6. ^ M.D. Krasowski & N.L. Harrison (2000). "The actions of ether, alcohol and alkane general anaesthetics on GABAA and glycine receptors and the effects of TM2 and TM3 mutations". British Journal of Pharmacology. 129 (4): 731–743. doi:10.1038/sj.bjp.0703087. PMC 1571881. PMID 10683198.
  7. ^ Lehman G and Knoefel PK (1938). Trichloroethanol, tribromoethanol, chloral hydrate, and bromal hydrate. J Pharmacol Exp Ther, 63: 453-465.


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