Structure via PubChem · Public domain (PubChem)
ethidium bromide
Sign in to saveAlso known as 2,7-diamino-10-ethyl-9-phenylphenanthridinium bromide, 2,7-diamino-9-phenyl-10-ethylphenanthridinium bromide, EtBr, Dromilac, homidium bromide
chemical compound
Chemical data
- Formula
- C21H20BrN3
- Molecular weight
- 394.3 g/mol
- IUPAC name
- 5-ethyl-3-imino-6-phenylphenanthridin-8-amine;hydrobromide
- SMILES
- CCN1C2=CC(=N)C=CC2=C3C=CC(=CC3=C1C4=CC=CC=C4)N.Br
- InChIKey
- ZMMJGEGLRURXTF-UHFFFAOYSA-N
- Polar surface area
- 53.1 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
12,400 papers- The Intercalator Ethidium Bromide Generates Covalent Adducts at Apurinic/Apyrimidinic Sites in DNA.Chemical research in toxicology · 2024
- Efficient removal of ethidium bromide from aqueous solutions using chromatin-loaded chitosan polyvinyl alcohol composites.Environmental science and pollution research international · 2024
- Ethidium bromide: destruction and decontamination of solutions.Analytical biochemistry · 1987
- Decontamination of ethidium bromide spills.Trends in genetics : TIG · 1990
- In Pseudomonas aeruginosa ethidium bromide does not induce its own degradation or the assembly of pumps involved in its efflux.Biochemical and biophysical research communications · 2004
via PubMed
Wikidata facts
- Mass
- 393.08406
Show 4 more facts
- chemical formula
- C₂₁H₂₀BrN₃
- Commons category
- Ethidium bromide
- melting point
- 248.5
- canonical SMILES
- Br.CCn1c2cc(=N)ccc-2c2ccc(N)cc2c1-c1ccccc1
via Wikidata · CC0
~8 min read
Article
Ethidium bromide (or homidium bromide, chloride salt homidium chloride) is an intercalating agent commonly used as a fluorescent tag (nucleic acid stain) in molecular biology laboratories for techniques such as agarose gel electrophoresis. It is commonly abbreviated as EtBr, which is also an abbreviation for bromoethane. To avoid confusion, some laboratories have used the abbreviation EthBr for this salt. When exposed to ultraviolet light, it will fluoresce with an orange colour, intensifying almost 20-fold after binding to DNA. Under the name homidium, it has been commonly used since the 1950s in veterinary medicine to treat trypanosomiasis in cattle. The high incidence of antimicrobial resistance makes this treatment impractical in some areas, where the related isometamidium chloride is used instead. Despite its reputation as a mutagen, tests have shown it to have low mutagenicity without metabolic activation.
Structure, chemistry, and fluorescence