Tribromoethanol

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]

Tribromoethanol
Clinical data
Trade namesAvertin
Other namesTribromoethyl alcohol
Identifiers
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.000.822
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]

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. "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.


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