Record Information
Version1.0
Creation Date2009-06-19 21:58:40 UTC
Update Date2026-04-05 17:30:39 UTC
Accession NumberCHEM001179
Identification
Common NameMerbromin
ClassSmall Molecule
DescriptionMerbromin is an organomercuric disodium salt compound and a fluorescein. It is used as a topical antiseptic for minor cuts and scrapes. Merbromin is also used as a biological dye to mark tissue margins, and as a metal dye in industrial dye penetrant inspection to detect metal fractures. Due to its mercury content, is is not available in some countries, such as the United States. Mercury is a heavy, silvery d-block metal and one of six elements that are liquid at or near room temperature and pressure. It is a naturally occuring substance, and combines with other elements such as chlorine, sulfur, or oxygen to form inorganic mercury compounds (salts). Mercury also combines with carbon to make organic mercury compounds. Bromine is a halogen element with the symbol Br and atomic number 35. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock. (15, 7, 13)
Contaminant Sources
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Bromide Compound
  • Ester
  • Industrial/Workplace Toxin
  • Mercury Compound
  • Organic Compound
  • Organobromide
  • Organometallic
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
2,7-Dibromo-4-hydroxymercurifluoresceine disodium saltChEBI
Disodium 2',7'-dibromo-4'-(hydroxymercury)fluoresceinChEBI
MerbrominaChEBI
MerbromineChEBI
MerbrominumChEBI
MerbrominKegg
MercurochromeChEBI
Chemical FormulaC20H8Br2HgNa2O6
Average Molecular Mass750.650 g/mol
Monoisotopic Mass749.819 g/mol
CAS Registry Number129-16-8
IUPAC Name[2,7-dibromo-3-oxo-6-(sodiooxy)-9-{2-[(sodiooxy)carbonyl]phenyl}-3H-xanthen-5-yl]mercurol
Traditional Name[2,7-dibromo-6-oxo-3-(sodiooxy)-9-{2-[(sodiooxy)carbonyl]phenyl}xanthen-4-yl]mercurol
SMILESO[Hg]C1=C2OC3=CC(=O)C(Br)=CC3=C(C2=CC(Br)=C1O[Na])C1=CC=CC=C1C(=O)O[Na]
InChI IdentifierInChI=1S/C20H9Br2O5.Hg.2Na.H2O/c21-13-5-11-17(7-15(13)23)27-18-8-16(24)14(22)6-12(18)19(11)9-3-1-2-4-10(9)20(25)26;;;;/h1-7,24H,(H,25,26);;;;1H2/q;3*+1;/p-3
InChI KeySQFDQLBYJKFDDO-UHFFFAOYSA-K
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthenes
Alternative Parents
Substituents
  • Xanthene
  • Benzoic acid or derivatives
  • Benzoyl
  • Aryl bromide
  • Metal aryl
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Carboxylic acid salt
  • Cyclic ketone
  • Oxacycle
  • Organic alkali metal salt
  • Carboxylic acid derivative
  • Organic metal salt
  • Monocarboxylic acid or derivatives
  • Organic transition metal salt
  • Organic transition metal moeity
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organobromide
  • Organomercurial-compound
  • Organometallic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic salt
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility20 mg/mL [GREEN,FJ (1990)]
Predicted Properties
PropertyValueSource
Water Solubility0.084 g/LALOGPS
logP3.77ALOGPS
logP4.3ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)15.6ChemAxon
pKa (Strongest Basic)2.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity118.48 m³·mol⁻¹ChemAxon
Polarizability46.74 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-0000000900-9713a535d1e0391db7d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0000000900-f30e35c1da29bf04b409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0o7j-2000009200-92cbda9b37d951bc2798Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000900-27f86aacead720f732b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-0000090700-fed070813a19378d729bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uyr-9001663300-a460d388100f6dc073adSpectrum
Toxicity Profile
Route of ExposureOral (9) ; inhalation (9) ; dermal (9)
Mechanism of ToxicityHigh-affinity binding of the divalent mercuric ion to thiol or sulfhydryl groups of proteins is believed to be the major mechanism for the activity of mercury. Through alterations in intracellular thiol status, mercury can promote oxidative stress, lipid peroxidation, mitochondrial dysfunction, and changes in heme metabolism. Mercury is known to bind to microsomal and mitochondrial enzymes, resulting in cell injury and death. For example, mercury is known to inhibit aquaporins, halting water flow across the cell membrane. It also inhibits the protein LCK, which causes decreased T-cell signalling and immune system depression. Mercury is also believed to inhibit neuronal excitability by acting on the postsynaptic neuronal membrane. It also affects the nervous system by inhibiting protein kinase C and alkaline phosphatase, which impairs brain microvascular formation and function, as well as alters the blood-brain barrier. Organic mercury exerts developmental effects by binding to tubulin, preventing microtubule assembly and causing mitotic inhibition. Mercury also produces an autoimmune response, likely by modification of major histocompatibility complex (MHC) class II molecules, self peptides, T-cell receptors, or cell-surface adhesion molecules. Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (16, 17, 6, 9, 3, 4, 5)
MetabolismOrganic mercury is absorbed mainly by the gastrointestinal tract, then distributed throughout the body via the bloodstream. Organic mercury complexes with free cysteine and the cysteine and sulfhydryl groups on proteins such as haemoglobin. These complexes are able to mimic methionine and thus be transported throughout the body, including through the blood-brain barrier and placenta. Organic mercury is metabolized into inorganic mercury, which is eventually excreted in the urine and faeces. Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (16, 18)
Toxicity ValuesLD50: 50 mg/kg (Intravenous, Mouse) (14)
Lethal Dose100 mg for an adult human (average for organic mercurials). (19)
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (12)
Uses/SourcesMerbromin is used as a topical antiseptic for minor cuts and scrapes. It is also used as a biological dye to mark tissue margins, and as a metal dye in industrial dye penetrant inspection to detect metal fractures. (13)
Minimum Risk LevelChronic Inhalation: 0.0002 mg/m3 (Mercury) (11)
Health EffectsMercury mainly affects the nervous system. Exposure to high levels of metallic, inorganic, or organic mercury can permanently damage the brain, kidneys, and developing fetus. Effects on brain functioning may result in irritability, shyness, tremors, changes in vision or hearing, and memory problems. Acrodynia, a type of mercury poisoning in children, is characterized by pain and pink discoloration of the hands and feet. Mercury poisoning can also cause Hunter-Russell syndrome and Minamata disease. Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (15, 16, 17, 9)
SymptomsCommon symptoms include peripheral neuropathy (presenting as paresthesia or itching, burning or pain), skin discoloration (pink cheeks, fingertips and toes), edema (swelling), and desquamation (dead skin peels off in layers). Bromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (16, 17, 1)
TreatmentEYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Concentrations
Not Available
DrugBank IDDB13392
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMerbromin
Chemspider IDNot Available
ChEBI ID6763
PubChem Compound ID9853537
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11141371
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12974562
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1692875
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18061533
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26177225
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=4433132
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=4971331
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=6177466
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=88168