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
SMILES
OCC(Br)(Br)Br
InChI
InChIKey=YFDSDPIBEUFTMI-UHFFFAOYSA-N
InChI=1S/C2H3Br3O/c3-2(4,5)1-6/h6H,1H2
| Molecular Formula | C2H3Br3O |
| Molecular Weight | 282.757 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16261153Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/10683198 | https://www.ncbi.nlm.nih.gov/pubmed/26566637 | https://www.ncbi.nlm.nih.gov/pubmed/15646539
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16261153
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/10683198 | https://www.ncbi.nlm.nih.gov/pubmed/26566637 | https://www.ncbi.nlm.nih.gov/pubmed/15646539
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 Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10683198 |
0.21 mM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16261153 |
Primary | Avertin Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The phytoestrogen coumestrol is a naturally occurring antagonist of the human pregnane X receptor. | 2008-04 |
|
| Dorsal hippocampal N-methyl-D-aspartate receptors underlie spatial working memory performance during non-matching to place testing on the T-maze. | 2008-01-10 |
|
| Loss of sugar detection by GLUT2 affects glucose homeostasis in mice. | 2007-12-12 |
|
| Maternal enrichment during pregnancy accelerates retinal development of the fetus. | 2007-11-14 |
|
| Functional relationship between subfornical organ cholinergic stimulation and nitrergic activation influencing cardiovascular and body fluid homeostasis. | 2007-10-04 |
|
| Reversal of systemic hypertension-associated cardiac remodeling in chronic pressure overload myocardium by ciglitazone. | 2007-09-07 |
|
| Transgenic upregulation of IK1 in the mouse heart is proarrhythmic. | 2007-09 |
|
| Radial glial dependent and independent dynamics of interneuronal migration in the developing cerebral cortex. | 2007-08-29 |
|
| Improve protective efficacy of a TB DNA-HSP65 vaccine by BCG priming. | 2007-08-22 |
|
| Cathepsin K null mice show reduced adiposity during the rapid accumulation of fat stores. | 2007-08-01 |
|
| Chronic intermittent hypoxia impairs baroreflex control of heart rate but enhances heart rate responses to vagal efferent stimulation in anesthetized mice. | 2007-08 |
|
| Modulation of microglial/macrophage activation by macrophage inhibitory factor (TKP) or tuftsin (TKPR) attenuates the disease course of experimental autoimmune encephalomyelitis. | 2007-07-16 |
|
| Enhanced effect of microdystrophin gene transfection by HSV-VP22 mediated intercellular protein transport. | 2007-07-08 |
|
| Complex seizure disorder caused by Brunol4 deficiency in mice. | 2007-07 |
|
| Perfluorochemical (PFC) liquid enhances recombinant adenovirus vector-mediated viral interleukin-10 (AdvIL-10) expression in rodent lung. | 2007-05-01 |
|
| N-Acetyl L-cysteine does not protect against premature age-related hearing loss in C57BL/6J mice: a pilot study. | 2007-04 |
|
| Lack of alpha-synuclein increases amyloid plaque accumulation in a transgenic mouse model of Alzheimer's disease. | 2007-03-16 |
|
| Matrix protein 2 vaccination and protection against influenza viruses, including subtype H5N1. | 2007-03 |
|
| Dynorphin activates quorum sensing quinolone signaling in Pseudomonas aeruginosa. | 2007-03 |
|
| Conversion of the BASE prion strain into the BSE strain: the origin of BSE? | 2007-03 |
|
| The calorically restricted ketogenic diet, an effective alternative therapy for malignant brain cancer. | 2007-02-21 |
|
| Effects of tribromoethanol-medetomidine combination on cycling and ovariectomized Sprague-Dawley rats. | 2007-02-01 |
|
| Cross-reactive neuraminidase antibodies afford partial protection against H5N1 in mice and are present in unexposed humans. | 2007-02 |
|
| Inhibition of drug metabolism by blocking the activation of nuclear receptors by ketoconazole. | 2007-01-11 |
|
| A role for Alström syndrome protein, alms1, in kidney ciliogenesis and cellular quiescence. | 2007-01-05 |
|
| Macrophage invasion contributes to degeneration of stria vascularis in Pendred syndrome mouse model. | 2006-12-22 |
|
| Physiological mouse brain Abeta levels are not related to the phosphorylation state of threonine-668 of Alzheimer's APP. | 2006-12-20 |
|
| Myocardial performance in conscious streptozotocin diabetic rats. | 2006-12-04 |
|
| Experimental allergic encephalomyelitis in pituitary-grafted Lewis rats. | 2006-08-23 |
|
| Modest phenotypic improvements in ASA-deficient mice with only one UDP-galactose:ceramide-galactosyltransferase gene. | 2006-08-07 |
|
| Comparing isoflurane with tribromoethanol anesthesia for echocardiographic phenotyping of transgenic mice. | 2006-07 |
|
| Embryonic pig pancreatic tissue transplantation for the treatment of diabetes. | 2006-07 |
|
| Vaginal microbicides: detecting toxicities in vivo that paradoxically increase pathogen transmission. | 2006-06-01 |
|
| Corticotropin-releasing factor (CRF) and urocortin promote the survival of cultured cerebellar GABAergic neurons through the type 1 CRF receptor. | 2006-06 |
|
| Compensation by tumor suppressor genes during retinal development in mice and humans. | 2006-05-03 |
|
| Toxic effects of methoxychlor on the episodic prolactin secretory pattern: possible mediated effects of nitric oxide production. | 2006-03-03 |
|
| Dynamic remodeling of dendritic arbors in GABAergic interneurons of adult visual cortex. | 2006-02 |
|
| Expression of hepatoma-derived growth factor family members in the adult central nervous system. | 2006-01-23 |
|
| THR0921, a novel peroxisome proliferator-activated receptor gamma agonist, reduces the severity of collagen-induced arthritis. | 2006 |
|
| Interaction between arginine vasopressin and angiotensin II receptors in the central regulation of sodium balance. | 2005-12-15 |
|
| Effects of hypothalamic neurodegeneration on energy balance. | 2005-12 |
|
| Respiratory and autonomic responses to microinjection of NMDA and AMPA into the commissural subnucleus of the NTS of awake rats. | 2005-11-23 |
|
| Efficient gene-driven germ-line point mutagenesis of C57BL/6J mice. | 2005-11-21 |
|
| A review of tribromoethanol anesthesia for production of genetically engineered mice and rats. | 2005-11 |
|
| Increased fidelity reduces poliovirus fitness and virulence under selective pressure in mice. | 2005-10 |
|
| Effects of anesthesia on diastolic function in mice assessed by echocardiography. | 2005-09 |
|
| Involvement of NMDA receptors in the hypotensive response to the injection of L-glutamate into the lateral hypothalamus of unanesthetized rats. | 2005-08-16 |
|
| A hybrid photoreceptor expressing both rod and cone genes in a mouse model of enhanced S-cone syndrome. | 2005-08 |
|
| Cell-autonomous death of cerebellar purkinje neurons with autophagy in Niemann-Pick type C disease. | 2005-07 |
|
| Anesthesia can cause sustained hyperglycemia in C57/BL6J mice. | 2005-02-21 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16261153
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10683198
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
Created
by
admin
on
Edited
Mon Mar 31 18:00:28 GMT 2025
by
admin
on
Mon Mar 31 18:00:28 GMT 2025
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| Record UNII |
149JI83A44
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| Record Status |
Validated (UNII)
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| Record Version |
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m503
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6400
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75-80-9
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2189
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DTXSID2023698
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Tribromoethanol
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C062527
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200-903-1
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149JI83A44
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CHEMBL1697852
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