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Tribromoethanol

Tribromoethanol
Tribromoethanol.svg
Clinical data
Trade namesAvertin
SynonymsTribromoethyl alcohol
Identifiers
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]

Tribromoethanol is an organobromine compound used as an anesthetic. 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] The tert-amyl alcohol acts as a weak hypnotic, in addition to improving the solubility of the tribromoethanol. Administered intravenously, tribromoethanol (Avertin) causes rapid and deep anesthesia followed by rapid and full postoperative recovery in small mammals.[4]

In the first half of the 20th century, Avertin was also used in humans as a general anesthetic or basal narcotic to induce unconsciousness prior to the administration of other anesthetic agents. It was administered rectally as a retention enema or by intravenous injection. Its rectal use was particularly favored for pediatrics, head or neck surgery, or in mentally unstable or anxious patients.[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. 2006: pdb.rec701. 2006. doi:10.1101/pdb.rec701.
  3. ^ "Guidelines for the Use of Tribromoethanol/Avertin Anesthesia" (PDF). National Cancer Institute.
  4. ^ Weiss, J.; Zimmermann, F. (1999). "Tribromoethanol (Avertin) as an anaesthetic in mice". Laboratory Animals. 33 (2): 192–193. doi:10.1258/002367799780578417. PMID 10780824.
  5. ^ G Edwards (1945). "Tribromethyl alcohol (avertin, bromethol), 1928-1945". Proceedings of the Royal Society of Medicine. 39 (2): 71–76. doi:10.1177/003591574503900203. 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.