2,2,2-Tribromoethanol, often called justtribromoethanol, is achemical compound withformulaBr3C−CH2OH. Its molecule can be described as that ofethanol, with the threehydrogen atoms in position 2 (on themethyl group) replaced bybromine. It is a white crystalline solid, soluble in water and other solvents, that absorbs strongly in theUV below 290nm.[2]
Tribromoethanol is used inmedicine andbiology as ananesthetic, and has been available commercially for that purpose by the trade nameAvertin. It was formerly used on humans[3] and is still often used on laboratory animals,[4] and to capture wild birds.[5]It is also used inplastics industry as apolymerizationinitiator.[6][7]
Tribromoethanol is often used to anesthetize laboratory animals, particularly rodents, before surgery.[4] As a solution intert-amyl alcohol, it has the brand nameAvertin.[8] Thetert-amyl alcohol acts as a weakhypnotic, 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.[9] Recently its safety for this purpose has been questioned.[10]
Tribromoethanol has also been long used as spiked grain bait to capturewild turkeys for research and wildlife management purposes.[5] However, the birds learn to avoid it, for over a year, after a single exposure, and will drive other flock members away from the bait when they detect it.[11]
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 retentionenema or by intravenous injection. Its rectal use was particularly favored for pediatrics, head or neck surgery, or in mentally unstable or anxious patients.[3]Electrophysiology studies showed that tribromoethanol acts as apositive allosteric modulator of the inhibitory GABAA and glycine receptors, a mechanism similar to that seen with the related compound2,2,2-trichloroethanol.[12]Bromal hydrate (2,2,2-tribromoethanol-1,1-diol), a compound also recognized to produce general anesthesia in animals, is metabolized to tribromoethanol.[13]
^abEvans RR, Goertz JW, Williams CT (July 1975). "Capturing wild turkeys with tribromoethanol".The Journal of Wildlife Management.39 (3):630–634.doi:10.2307/3800410.JSTOR3800410.
^abMoineau G, Minet M, Dubois P, Teyssie P, Senninger T, Jérôme R (January 1999). "Controlled radical polymerization of (meth) acrylates by ATRP with NiBr2 (PPh3) 2 as catalyst".Macromolecules.32 (1):27–35.doi:10.1021/ma980995u.
^abVieira RP, Ossig A, Perez JM, Grassi VG, Petzhold CL, Peres AC, Costa JM, Lona LM (October 2015). "Styrene ATRP using the new initiator 2,2,2-tribromoethanol: Experimental and simulation approach".Polymer Engineering & Science.55 (10):2270–2276.doi:10.1002/pen.24113.
^Weiss J, Zimmermann F (April 1999). "Tribromoethanol (Avertin) as an anaesthetic in mice".Laboratory Animals.33 (2):192–193.doi:10.1258/002367799780578417.PMID10780824.
^Robert E. Meyer and Richard E. Fish (2005) "A review of tribromoethanol anesthesia for production of genetically engineered mice and rats".Lab Animal, volume 34, pages 47–52.Meyer RE, Fish RE (November 2005). "A review of tribromoethanol anesthesia for production of genetically engineered mice and rats".Lab Animal.34 (10):47–52.doi:10.1038/laban1105-47.PMID16261153.S2CID21759580.
^Davis JR, Guynn Jr DC, Hyder BD (October 1994). "Feasibility of Using Tribromoethanol to Recapture Wild Turkeys".Wildlife Society Bulletin.22 (3):496–500.JSTOR3783394.
