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Details

Stereochemistry ACHIRAL
Molecular Formula C2H3Br3O
Molecular Weight 282.757
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIBROMOETHANOL

SMILES

OCC(Br)(Br)Br

InChI

InChIKey=YFDSDPIBEUFTMI-UHFFFAOYSA-N
InChI=1S/C2H3Br3O/c3-2(4,5)1-6/h6H,1H2

HIDE SMILES / InChI

Molecular Formula C2H3Br3O
Molecular Weight 282.757
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Tribromoethanol is a popular injectable anesthetic agent commonly used for embryo-transfer surgery for the generation of transgenic mice and sometimes rats. In humans and animals, Tribromoethanol produces a generalized CNS depression, including both the respiratory and cardiovascular centers. It undergoes conjugation with glucuronic acid during metabolism in the liver, followed by excretion in the urine as TBE glucuronate. Tribromoethanol causes rapid and deep anesthesia followed by rapid and full postoperative recovery, but the margin of safety between anesthetic and the lethal dose is narrow. Depression of respiration and circulation, together with its general unpredictability, eventually discouraged its use. Although Tribromoethanol solutions are often referred to as Avertin, this is a misnomer. Avertin was the trade name for Winthrop Laboratories’ proprietary Tribromoethanol formulation, which is no longer available. Marketing of pharmaceutical-grade Tribromoethanol took place under several proprietary names, including Avertin, Bromethol, Ethobrom, and Narkolan, each as a 66.7% (w/w) solution of Tribromoethanol in tertiary-amyl alcohol, wherein each milliliter contained 1 g of Tribromoethanol. Although pharmaceutical-grade TBE has not been commercially available or routinely used for human or veterinary anesthesia for several years, the agent has received widespread acceptance for use in the various manipulations required for the production of genetically engineered mice and rats. Tribromoethanol is an attractive anesthetic choice for many researchers because it is easy and inexpensive to make in the laboratory from readily available reagents, requires no special equipment for its administration, and is not subject to federal or state drug enforcement agency storage or accountability regulations. More importantly, the i.p. injection of TBE results in the simple and rapid induction of short-term surgical anesthesia sufficient for the vasectomy, embryo transfer, and tail amputation for Southern blot analysis—all necessary elements in the production of genetically engineered animals.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.21 mM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Avertin

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Rats: 200 mg/kg, 300 mg/kg, or 400 mg/kg Mice: 125 mg/kg to 500 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
Wild-type or mutated receptor cDNAs were expressed via the vector pCIS2 which contains one copy of the strong promoter from cytomegalovirus and a polyadenylation sequence from SV40. HEK 293 cells were used for electrophysiological experiments 2 ± 5 days following cDNA transfection. The extracellular medium contained (in mM): NaCl 145, KCl 3, CaCl2 1.5, MgCl2 1, D-glucose 5.5 and HEPES 10, pH 7.4, osmolarity 320 ± 330 mosmol. The electrode solution contained (in mM): N-methyl-D-glucamine hydrochloride 145, K2ATP 5, HEPES/KOH 5, MgCl2 2, CaCl2 0.1 and EGTA 1.1, pH 7.2, osmolarity 315 mosmol. Pipette-to-bath resistance was 4 ±6 MO. Cells were voltage-clamped at 760 mV. All drugs were rapidly (550 ms exchange time) applied to the cell by local perfusion using a motor-driven solution exchange device. Laminar flow was maintained by applying all solutions at identical flow rates via a multi-channel infusion pump
Substance Class Chemical
Record UNII
149JI83A44
Record Status Validated (UNII)
Record Version