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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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Originator

Sources: Sydney Univ. Reprints 3, (Ser. 9;No. 24),

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.21 mM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Avertin

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The actions of ether, alcohol and alkane general anaesthetics on GABAA and glycine receptors and the effects of TM2 and TM3 mutations.
2000 Feb
Effects of tribromoethanol anesthesia on echocardiographic assessment of left ventricular function in mice.
2001 Feb
Effects of avertin versus xylazine-ketamine anesthesia on cardiac function in normal mice.
2001 Nov
Inhibition of pilocarpine-induced salivation in rats by central noradrenaline.
2002 Jun
Embryonic stem cells and mice expressing different GFP variants for multiple non-invasive reporter usage within a single animal.
2002 Jun 11
A method to study preovulatory surges of gonadotropins.
2003 Aug
Anesthetics in GEM: does TBE make the grade?
2003 Feb
Role of glucocorticoids in mediating effects of fasting and diabetes on hypothalamic gene expression.
2003 Jul 9
Potentiation of ionising radiation by targeting tumour necrosis factor alpha using a bispecific antibody in human pancreatic cancer.
2003 Nov 17
Identification of in vitro parameters predictive of graft function: a study in an animal model of islet transplantation.
2004 Apr
Exposure to warmer postoperative temperatures reduces hypothermia caused by anaesthesia and significantly increases the implantation rate of transferred embryos in the mouse.
2004 Jan
Influence of O(3)/O(2)-pneumoperitoneum as an oxidative stressor on duration of anaesthesia, loss of different reflexes and cytokine mRNA expression.
2004 Jul
In vivo imaging of amyloid-beta deposits in mouse brain with multiphoton microscopy.
2005
Adult murine skeletal muscle contains cells that can differentiate into beating cardiomyocytes in vitro.
2005 Apr
A hybrid photoreceptor expressing both rod and cone genes in a mouse model of enhanced S-cone syndrome.
2005 Aug
Involvement of NMDA receptors in the hypotensive response to the injection of L-glutamate into the lateral hypothalamus of unanesthetized rats.
2005 Aug 16
Enhanced macromolecular diffusion in brain extracellular space in mouse models of vasogenic edema measured by cortical surface photobleaching.
2005 Mar
Increased fidelity reduces poliovirus fitness and virulence under selective pressure in mice.
2005 Oct
THR0921, a novel peroxisome proliferator-activated receptor gamma agonist, reduces the severity of collagen-induced arthritis.
2006
Macrophage invasion contributes to degeneration of stria vascularis in Pendred syndrome mouse model.
2006 Dec 22
Dynamic remodeling of dendritic arbors in GABAergic interneurons of adult visual cortex.
2006 Feb
Expression of hepatoma-derived growth factor family members in the adult central nervous system.
2006 Jan 23
Vaginal microbicides: detecting toxicities in vivo that paradoxically increase pathogen transmission.
2006 Jun 1
Compensation by tumor suppressor genes during retinal development in mice and humans.
2006 May 3
Radial glial dependent and independent dynamics of interneuronal migration in the developing cerebral cortex.
2007 Aug 29
Cross-reactive neuraminidase antibodies afford partial protection against H5N1 in mice and are present in unexposed humans.
2007 Feb
The calorically restricted ketogenic diet, an effective alternative therapy for malignant brain cancer.
2007 Feb 21
A role for Alström syndrome protein, alms1, in kidney ciliogenesis and cellular quiescence.
2007 Jan 5
Modulation of microglial/macrophage activation by macrophage inhibitory factor (TKP) or tuftsin (TKPR) attenuates the disease course of experimental autoimmune encephalomyelitis.
2007 Jul 16
Matrix protein 2 vaccination and protection against influenza viruses, including subtype H5N1.
2007 Mar
Conversion of the BASE prion strain into the BSE strain: the origin of BSE?
2007 Mar
Functional relationship between subfornical organ cholinergic stimulation and nitrergic activation influencing cardiovascular and body fluid homeostasis.
2007 Oct 4
The phytoestrogen coumestrol is a naturally occurring antagonist of the human pregnane X receptor.
2008 Apr
Patents

Patents

Sample Use Guides

Rats: 200 mg/kg, 300 mg/kg, or 400 mg/kg Mice: 125 mg/kg to 500 mg/kg
Route of Administration: Intraperitoneal
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 Fri Dec 15 15:32:19 GMT 2023
Edited
by admin
on Fri Dec 15 15:32:19 GMT 2023
Record UNII
149JI83A44
Record Status Validated (UNII)
Record Version
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Name Type Language
TRIBROMOETHANOL
MI  
Systematic Name English
TRIBROMOETHANOL [MI]
Common Name English
TRIBROMOETHYL ALCOHOL [MART.]
Common Name English
NSC-2189
Code English
2,2,2-TRIBROMOETHANOL
Systematic Name English
TRIBROMOETHYL ALCOHOL
MART.  
Systematic Name English
Code System Code Type Description
MERCK INDEX
m503
Created by admin on Fri Dec 15 15:32:19 GMT 2023 , Edited by admin on Fri Dec 15 15:32:19 GMT 2023
PRIMARY Merck Index
PUBCHEM
6400
Created by admin on Fri Dec 15 15:32:19 GMT 2023 , Edited by admin on Fri Dec 15 15:32:19 GMT 2023
PRIMARY
CAS
75-80-9
Created by admin on Fri Dec 15 15:32:19 GMT 2023 , Edited by admin on Fri Dec 15 15:32:19 GMT 2023
PRIMARY
NSC
2189
Created by admin on Fri Dec 15 15:32:19 GMT 2023 , Edited by admin on Fri Dec 15 15:32:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID2023698
Created by admin on Fri Dec 15 15:32:19 GMT 2023 , Edited by admin on Fri Dec 15 15:32:19 GMT 2023
PRIMARY
WIKIPEDIA
Tribromoethanol
Created by admin on Fri Dec 15 15:32:19 GMT 2023 , Edited by admin on Fri Dec 15 15:32:19 GMT 2023
PRIMARY
MESH
C062527
Created by admin on Fri Dec 15 15:32:19 GMT 2023 , Edited by admin on Fri Dec 15 15:32:19 GMT 2023
PRIMARY
DRUG CENTRAL
2731
Created by admin on Fri Dec 15 15:32:19 GMT 2023 , Edited by admin on Fri Dec 15 15:32:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-903-1
Created by admin on Fri Dec 15 15:32:19 GMT 2023 , Edited by admin on Fri Dec 15 15:32:19 GMT 2023
PRIMARY
FDA UNII
149JI83A44
Created by admin on Fri Dec 15 15:32:19 GMT 2023 , Edited by admin on Fri Dec 15 15:32:19 GMT 2023
PRIMARY
ChEMBL
CHEMBL1697852
Created by admin on Fri Dec 15 15:32:19 GMT 2023 , Edited by admin on Fri Dec 15 15:32:19 GMT 2023
PRIMARY