Mercury dibromofluorescein disodium salt
Basic information
- CAS
129-16-8- Standard SMILES
O.O=C([O-])c1ccccc1-c1c2cc(Br)c(=O)cc-2oc2[c]([Hg])c([O-])c(Br)cc12.[Na+].[Na+]- InChIKey
KQSRXDXJGUJRKE-UHFFFAOYSA-L- Molecular formula
- C20H9Br2HgNa2O6
- Average molar mass
- 751.7 g/mol
- Monoisotopic mass
- 750.82677
Overview
Merbromin is an organic sodium salt that is 2,7-dibromo-4-hydroxymercurifluorescein in which the carboxy group and the phenolic hydroxy group have been deprotonated and the resulting charge is neutralised by two sodium ions. It has a role as an antiseptic drug, a fluorochrome and a histological dye. It contains a 2,7-dibromo-4-hydroxymercurifluorescein(2-).
Names & identifiers
- Preferred name
- Mercury dibromofluorescein disodium salt
- IUPAC
- disodium;[2,7-dibromo-9-(2-carboxylatophenyl)-3-oxido-6-oxoxanthen-4-yl]mercury;hydrate
- English name
- MERBROMIN
- Molecular formula
- C20H11Br2HgNaO6
- Molecular weight
- 730.69
Names & synonyms
Mercury dibromofluorescein disodium saltdisodium;[2,7-dibromo-9-(2-carboxylatophenyl)-3-oxido-6-oxoxanthen-4-yl]mercury;hydrateCinfacrominMerbrominoMercuriocromoSupercromeSodium merbrominSodium mercuresceinMerbromin N.F XIISCHEMBL25312SPECTRUM1500637orb1310778
Show more names
Hg2sb2o7fluorochromeMERCUROCHROMEdomfEmcerolflavurolChromineEkakromeMERBROMINMarbromin
HMS501E17DTXSID701015061HMS1921M15HMS2092E12CCG-39726AKOS015903744AKOS037515483DB13392
Database identifiers
- CAS
129-16-8、15015-80-2- PubChem CID
- 441373
- DTXSID
Properties
Computed structural properties
- Topological polar surface area
- 90.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 801
Physicochemical properties
- Melting point
- 300 °C · ≥300 °C
- storage temp.
- Poison room
- solubility
- 50 mg/mL · Water : ≥ 50 mg/mL (66.43 mM);DMSO : 6.67 mg/mL (8.86 mM)
- form
- crystalline
- color
- green
- Odor
- Odorless
- PH Range
- 8.5 · 8.5 - 9
- Water Solubility
- 2.561 g/L · 2.561g/L at 25℃
- Merck
- 13 · 13,5892
- Stability
- Stable. Incompatible with strong oxidizing agents, strong acids.
- InChI
- InChI=1S/C20H9Br2O5.Hg.Na.H2O.H/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20;;;;/h1-7,23-24H;;;1H2;/q;+1;;;/p-1
- InChIKey
- DWCWFRMTTRCCLB-UHFFFAOYSA-M
- SMILES
- O=C1C2C=CC=CC=2C2(C3=CC(Br)=C(O)C=C3OC3C(=C(O)C(Br)=CC2=3)[Hg]O)O1.[NaH]
- LogP
- 1.418 at · 1.418 at 25℃
- CAS DataBase Reference
- 129 · 129-16-8(CAS DataBase Reference)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety & protection
Minimum Risk LevelChronic Inhalation: 0.0002 mg/m3 (Mercury) (L134)
Toxicology
Treatment
EYES: 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.
Health Effects
Mercury 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. (L625, L626, L627, L7)
Exposure RoutesOral (L7) ; inhalation (L7) ; dermal (L7)
Toxicity Summary
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Organic 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. (L626, T11)
Uses & manufacturing
UsesMerbromin 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. (L264)
Applications
Usesanthelmintic
UsesAntiseptic and applied topically
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: An organic sodium salt that is 2,7-dibromo-4-hydroxymercurifluorescein in which the carboxy group and the phenolic hydroxy group have been deprotonated and the resulting charge is neutralised by two sodium ions.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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