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Ethidium bromide

Ethidium bromide
Ethidium bromide.svg
Ethidium-bromide-from-monohydrate-xtal-1971-3D-balls-B.png
Ethidium-bromide-monohydrate-xtal-1971-3D-SF.png
Names
IUPAC name
3,8-Diamino-5-ethyl-6-phenylphenanthridinium bromide
Other names
2,7-Diamino-10-ethyl-6-phenylphenanthridinium bromide, 2,7-Diamino-10-ethyl-9-phenylphenanthridinium bromide, 3,8-Diamino-1-ethyl-6-phenylphenantridinium bromide, 5-Ethyl-6-phenyl-phenanthridine-3,8-diamine bromide, Ethidium bromide, Homidium bromide, EtBr
Identifiers
1239-45-8 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:4883 YesY
ChEMBL ChEMBL284328 YesY
ChemSpider 14034 YesY
ECHA InfoCard 100.013.622
EC Number 214-984-6
KEGG C11161 YesY
PubChem 14710
RTECS number SF7950000
UNII 059NUO2Z1L YesY
Properties
C21H20BrN3
Molar mass 394.294 g/mol
Appearance Purple-red solid
Melting point 260 to 262 °C (500 to 504 °F; 533 to 535 K)
~ 40 g/l
Pharmacology
QP51AX06 (WHO)
Hazards
R-phrases R25 R36/37/38 R46
S-phrases S22 S24/25 S26 S36/37/39 S45 S53
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazard BIO: Biohazardous. E.g., smallpox virusNFPA 704 four-colored diamond
Flash point > 100 °C (212 °F; 373 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Ethidium bromide 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. 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, a disease caused by trypanosomes. The high incidence of antibiotic resistance makes this treatment impractical in some areas, where the related isometamidium chloride is used instead. Ethidium bromide may be a mutagen, although this depends on the organism exposed and the circumstances of exposure.

As with most fluorescent compounds, ethidium bromide is aromatic. Its core heterocyclic moiety is generically known as a phenanthridine, an isomer of which is the fluorescent dye acridine. Absorption maxima of EtBr in aqueous solution are at 210 nm and 285 nm, which correspond to ultraviolet light. As a result of this excitation, EtBr emits orange light with wavelength 605 nm.


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Wikipedia

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