Ethidium bromide

Not to be confused with Ethyl bromide.
Ethidium bromide
Names
Preferred IUPAC name
3,8-Diamino-5-ethyl-6-phenylphenanthridin-5-ium 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
  • EthBr
Identifiers
3D model (JSmol)
3642536
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.013.622 Edit this at Wikidata
EC Number
  • 214-984-6
KEGG
RTECS number
  • SF7950000
UNII
UN number 2811
  • InChI=1S/C21H19N3.BrH/c1-2-24-20-13-16(23)9-11-18(20)17-10-8-15(22)12-19(17)21(24)14-6-4-3-5-7-14;/h3-13,23H,2,22H2,1H3;1H checkY
    Key: ZMMJGEGLRURXTF-UHFFFAOYSA-N checkY
  • InChI=1/C21H19N3.BrH/c1-2-24-20-13-16(23)9-11-18(20)17-10-8-15(22)12-19(17)21(24)14-6-4-3-5-7-14;/h3-13,23H,2,22H2,1H3;1H
    Key: ZMMJGEGLRURXTF-UHFFFAOYAD
  • CC[n+]1c2cc(N)ccc2c3ccc(N)cc3c1c4ccccc4.[Br-]
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
QP51DX03 (WHO)
Hazards[1]
GHS labelling:
GHS06: ToxicGHS08: Health hazard
Danger
H302, H330, H341
P201, P202, P260, P284, P301+P312, P304+P340+P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
1
0
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).
checkY verify (what is checkY☒N ?)

Ethidium bromide (or homidium bromide,[2] chloride salt homidium chloride)[3][4] 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.[5] 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.[6][7]

  1. ^ "GESTIS-Stoffdatenbank". gestis.dguv.de (in German). Retrieved 22 November 2021.
  2. ^ Cite error: The named reference Hom-Br-PubChem was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference Kinabo-1993 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference Hom-Cl-PubChem was invoked but never defined (see the help page).
  5. ^ Stevenson P, Sones KR, Gicheru MM, Mwangi EK (May 1995). "Comparison of isometamidium chloride and homidium bromide as prophylactic drugs for trypanosomiasis in cattle at Nguruman, Kenya". Acta Tropica. 59 (2): 77–84. doi:10.1016/0001-706X(94)00080-K. PMID 7676909.
  6. ^ Lowe, Derek (2016-04-18). "The Myth of Ethidium Bromide". In the Pipeline. Retrieved 2019-02-28.
  7. ^ "Ethidium Bromide: Swap or Not | UCSB Sustainability". sustainability.ucsb.edu. Retrieved 2023-02-08.