HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
3,8-Diamino-1-ethyl-6-phenylphe-nantridinium-bromid
ETBR · Ethidium bromide solution · HOMIDIUM BROMIDE · Homidium · Rd1572 · Dromilac · -Cellstain-Eb · EthD (bromide)
Identifikatoren & physikalische Daten
| CAS No. | 1239-45-8 |
|---|---|
| Summenformel | C21H20N3.Br |
| Durchschnittliche Molmasse | 394,3 g/mol |
| Monoisotopische Masse | 393,08405974 g/mol |
| SMILES | CC[n+]1c(-c2ccccc2)c2cc(N)ccc2c2ccc(N)cc21.[Br-] |
| InChIKey | ZMMJGEGLRURXTF-UHFFFAOYSA-N |
| PubChem CID | 14710 |
| ChEMBL | CHEMBL284328 |
| ChEBI | CHEBI:4883 |
| EC No. | 214-984-6 |
| DTXSID | DTXSID8025258 |
| Lokaler Name | 3,8-Diamino-1-ethyl-6-phenylphe-nantridinium-bromid |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 55,9 |
|---|---|
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 25 |
| Formalladung | 0 |
| Komplexität | 419 |
| Stoffklassen | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| LogP (Verteilungskoeffizient) | log Kow= -0.38 /Estimated/-1.1 |
| Geschmack | Bitter tasting |
| Dichte | 0.34 g/cm³1.3739 (rough estimate) |
| Color/Form | Dark red crystals from alcoholMaroon powder |
| Löslichkeit | Solubility in 2-methoxyethanol is 20 mg/mLethanol, 2 mg/mLSoluble in 750 parts chloroform at 20 °CSoluble in 20 parts water at 20 °CSolubility in water, g/100ml at 20 °C: 5H2O: 10 mg/mL, opaque, strongly red40 g/L (25 ºC) |
| Flammpunkt | >100 °C>100°C |
| Decomposition | When heated to decomposition it emits very toxic fumes of /hydrogen bromide and nitrogen oxides/. |
| Schmelzpunkt | 260-262 °C (decomposes)238-240 °C260-262 °C (dec.)(lit.) |
| Dampfdruck | 1.2X10-12 mm Hg at 25 °C /Estimated/Vapor pressure at 25 °C: negligible |
| Henry-Konstante | Henry's Law constant= 1.8X10-20 atm-cu m/mole at 25 °C /Estimated/ |
| Physical Description | Dark red solid[Merck Index] Red to brown solid[ICSC] Dark red powder[Sigma-Aldrich MSDS]RED-TO-BROWN CRYSTALS. |
| Brechungsindex | 1.6700 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | powder |
| Farbe | Red to dark purple |
| pH | 4.4 (20°C, 10g/L in H2O) |
| Geruch | Odorless solid |
| Merck | 14,4731 |
| BRN | 3642536 |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | Electroluminescent displaysphotoresists |
| 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 |
| InChIKey | ZMMJGEGLRURXTF-UHFFFAOYSA-N |
| SMILES | [Br-].CC[n+]1c(-c2ccccc2)c3cc(N)ccc3c4ccc(N)cc14 |
| CAS Datenbank | 1239-45-8(CAS DataBase Reference) |
| EPA chemische Informationen | Phenanthridinium, 3,8-diamino-5-ethyl-6-phenyl-, bromide (1239-45-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P264, P270, P271, P280, P284, P301+P317, P304+P340, P316, P318, P320, P330, P403+P233, P405, and P501 (click each P-code to see the statement)H302 (97.1%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P261, P264, P270, P271, P280, P284, P301+P317, P304+P340, P316, P318, P320, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Phenanthridinium, 3,8-diamino-5-ethyl-6-phenyl-, bromideEthidium bromide: HSNO Approval: HSR004464 Approved with controls |
| Weitere Sicherheitsinformationen | IMAP assessments - Phenanthridinium, 3,8-diamino-5-ethyl-6-phenyl-, bromide: Human health tier I assessment |
| Brandgefahren | Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| Gefahrenübersicht | A skin, eye, and respiratory tract irritant[ICSC] May cause irritationToxic by ingestionHighly toxic by inhalationMutagenic effects observed in vitro[Sigma-Aldrich MSDS] See Propidium iodide. |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: I |
| Chemical Dangers | Decomposes on heating. This produces toxic gases including hydrogen bromide (see ICSC 0282) and nitrogen oxides (see ICSCs 0930 and 1311). Reacts violently with strong oxidants. |
| Packaging and Labelling | Do not transport with food and feedstuffs. |
| Hazard Classes and Categories | Acute Tox. 4 (97.1%)Germ cell mutagenicity - category 2Muta. 2 |
| Shipment Methods and Regulations | Employers /must/ ensure that labels on incoming containers of hazardous chemicals are not removed or defaced. Employers /must/ maintain any material safety data sheets that are received with incoming shipments of hazardous chemicals, and ensure that they are readily accessible to laboratory employees. |
| Brandbekämpfung | Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Rinse and then wash skin with water and soap.Rinse with plenty of water for several minutes (remove contact lenses if easily possible).Rinse mouth. |
| Sichere Lagerung | Fireproof. Separated from strong oxidants and food and feedstuffs. |
| Lagerbedingungen | Ethidium bromide should be handled in the laboratory using the "basic prudent practices" described in Chapter 5.C. Because of its mutagenicity, stock solutions of this compound should be prepared in a fume hood, and protective gloves should be worn at all times while handling this substance. Operations capable of generating ethidium bromide dust or aerosols of ethidium bromide solutions should be conducted in a fume hood to prevent exposure by inhalation. |
| Entsorgungsverfahren | Excess ethidium bromide and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines. For more information on disposal procedures see Chapter 7 of this volume.SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Verschüttetes entsorgen | Sweep spilled substance into sealable containers. Then wash away with plenty of water. |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. NO contact with strong oxidizing agents. |
| Inhalation Risk | A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered. |
| Skin Prevention | Protective gloves. |
| Exposure Prevention | AVOID ALL CONTACT! |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| Wechselwirkungen | Bleomycin is an anti-tumor agent whose cytotoxicity is related to the introduction of both single-stranded and double-stranded breaks in cellular DNA. In an assay using isolated nuclei, low levels of ethidium bromide substantially increased bleomycin induced release of nuclear chromatin. Treatment of mouse L1210 leukemia cells in vitro with low levels of ethidium bromide followed 1 hr later by bleomycin produced a synergistic effect that was 8 fold greater than that expected from the additive cytotoxicity of each drug alone. Interestingly, when the order of drug addition was reversed the drug synergism was much reduced (2 fold). The combination of DNA unwinding and strand scission agents may represent a novel and rational approach to the chemotherapy of cancer. |
| Expositionspfade | The substance can be absorbed into the body by inhalation and by ingestion. |
| Signs and Symptoms | Cough.Redness.Sore throat. |
| ICSC Environmental Data | Environmental effects from the substance have not been investigated adequately. |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ Homidium was a moderate eye irritant but not a skin irritant in the rabbit. /Homidium//LABORATORY ANIMALS: Acute Exposure/ Respiratory impairment was seen after intravenous administration while necrosis at the injection site occurred following subcutaneous injection. /Homidium//LABORATORY ANIMALS: Acute Exposure/ The major signs of toxicity noted after intravenous and subcutaneous dosing /in rats/ included tremors, prostration and sedation. /Homidium//LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Peripheral nerve ultrastructure was assessed after single or multiple local injections of the intercalating dye ethidium bromide. Thirty-four adult Wistar rats of both sexes were divided into five groups and maintained in a controlled environment with rat chow and water ad libitum throughout the experiment. The experimental animals were injected with 1 microl of 0.1% ethidium bromide in 0.9% saline into the central third of the left sciatic nerve 1 (group 1), 2 (group 2), 4 (group 3), 6 (group 4) or 8 (group 5) times. In groups 2 to 5 the injections were made at 28-day intervals. Control animals received the same amount of 0.9% saline. The animals were killed at different times after injection: group 1 at 7 days (2 rats) and 15 days (2 rats)for groups 2, 3, 4 and 5, all rats were killed 10 days after the last injection and the lesions were investigated by light and transmission electron microscopy. In the acute lesions, intoxicated Schwann cells showed a vacuolated cytoplasm and separation of the sheaths from the axon. Myelin sheaths underwent progressive vesiculation and subsequent segmental demyelination. Myelin debris were withdrawn by macrophages and remyelination by Schwann cells was prominent. With the increase in the number of injections collagen fibers also increased in number and progressively enveloped smaller numbers of remyelinated axons composing new fascicles. Wallerian degeneration of fibers apparently not affected by ethidium bromide was more intense in the nerves from groups 4 and 5. The peripheral nerve repairs itself after demyelinating challenges with a profusion of collagen fibers and new fasciculations. This experimental model is valid to mimic recurrent demyelinating neuropathies.For more Non-Human Toxicity Excerpts (Complete) data for ETHIDIUM BROMIDE (8 total), please visit the HSDB record page. |
| Antidote and Emergency Treatment | Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/ |
| Toxicity Data | LC50 (rat) = 11,000-134,000 mg/m3/1hr |
| Non-Human Toxicity Values | LD50 Mouse subcutaneous 110 mg/kgLD50 Mouse intraperitoneal 20 mg/kgLD50 Rat iv 27 mg/kgLD50 Rat sc 80 mg/kgFor more Non-Human Toxicity Values (Complete) data for ETHIDIUM BROMIDE (6 total), please visit the HSDB record page. |
| F | 8-9 |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2811 6.1/PG 1 |
| Zollcode | 29339990 |
| RTECS-Nr. | SF7950000 |
| R-Sätze (R) | 23-68-36/37/38-26-21/22-22 |
| Toxizität | Intercalating dye widely used to stain DNA in gels and gradients. The DNA can be visualized readily by irradiation with ultraviolet light, as little as 0.5 μg of DNA being detectable by such methods. Ethidium bromide is also added to cesium chloride density gradients, since as an intercalating molecule it binds more readily to linear DNA than to closed collinear circles of DNA (such as plasmids). Binding of ethidium bromide reduces the density of DNA, thus covalent circles of DNA have higher densities at saturating concentrations of ethidium bromide, permitting the separation of plasmid DNA. Ethidium bromide is a putative carcinogen. |
| Gefahrensymbole | T,T+ |
| Sicherheitshinweise (S) | 36/37-45-36/37/39-28A-26-22-28-63 |
| Gefahrenklasse | 6.1Acute Tox. 1 InhalationAcute Tox. 4 OralMuta. 2 |
| Verpackungsgruppe | I |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Gefahrstoffdaten | 1239-45-8(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Ethidium bromide (EtBr) is the most commonly used nucleic acid stain for PAGE or agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the background is not necessary with a low stain concentration (10 μg/ml). Ethidium bromide has been used in a number of fluorimetric assays for nucleic acids. It has been shown to bind to single-stranded DNA (although not as strongly) and triple-stranded DNA. Because of its ability to bind to DNA, EtBr is an inhibitor of DNA polymerase. Antiprotozoal (Trypanosoma).