Methylene Blue Trihydrate
Grundinformationen
- CAS
7220-79-3- Standard-SMILES
CN(C)c1ccc2nc3ccc(=[N+](C)C)cc-3sc2c1.O.O.O.[Cl-]- InChIKey
XQAXGZLFSSPBMK-UHFFFAOYSA-M- Summenformel
- C16H18N3S.Cl.3H2O
- Durchschnittliche Molmasse
- 373,9 g/mol
- Monoisotopische Masse
- 373,12269031
Überblick
Methylene blue trihydrate appears as odorless or almost odorless dark green crystals with bronze luster or dark green crystalline powder. pH (1% solution in water) 3 to 4.5. (NTP, 1992)
Namen und Bezeichner
- Bevorzugter Name
- Methylene Blue Trihydrate
- IUPAC
- [7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium;chloride;trihydrate
- Englischer Name
- Methylene Blue trihydrate
- Summenformel
- C16H20ClN3OS
- Molmasse
- 337.87
Namen und Synonyme
Methylene Blue trihydrate7220-79-3Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride, trihydrateDTXSID00256003,7-Bis(dimethylamino)phenothiazin-5-ium chloride trihydrateMethylene blue (USP)C.I. Basic Blue 9, trihydrateCCRIS 9312UNII-T42P99266KMethylene blue [USP]DTXCID705600METHYLENE BLUE TRIHYDRATE [MI]
Weitere Namen anzeigen
METHYLENE BLUE HYDRATECI 52015Methylthioninium Chloride TrihydrateMethylthioniniumMethylene Blue, CPMETHYLTHIONINE CHLORIDEMETHYLENE BLUE CHLORIDEMETHYLENE BLUE INDICATORMethylene Blue trihydrateeMethyltltioninium Chloride
NSC 759135C.I. Basic Blue 9, trihydrate (8CI)RefChem:158183METHYLTHIONINE TRIHYDRATETETRAMETHYLENE BLUE TRIHYDRATEMETHYLTHIONINE CHLORIDE TRIHYDRATE3,7Bis(dimethylamino)phenazathionium chloride trihydrate3,7Bis(dimethylamino)phenothiazin5ium chloride trihydrate
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 46,9 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 483
Experimentelle und physikochemische Eigenschaften
Chemical ClassesDyes -> Azine Dyes
Solubilitygreater than or equal to 100 mg/mL at 72 °F (NTP, 1992)
Melting Point374 °F (decomposes) (NTP, 1992)
Physical Description
Methylene blue trihydrate appears as odorless or almost odorless dark green crystals with bronze luster or dark green crystalline powder. pH (1% solution in water) 3 to 4.5. (NTP, 1992)
Dark green odorless solid with a bronze luster; [Merck Index] Hygroscopic; [CAMEO] Dark green powder; [Sigma-Aldrich MSDS]
Physikochemische Eigenschaften
- Schmelzpunkt
- 190 °C · 190 °C (dec.)(lit.)
- Dichte
- 0.98 g/mL · 0.98 g/mL at 25 °C
- Flammpunkt
- 14 °C · 14 °C
- storage temp.
- no restrictions.
- Löslichkeit
- Soluble in water, chloroform; sparingly soluble in ethanol
- Aggregatzustand
- Solid
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 7.6% (7 of 92) of reports.
Warning
H302 (92.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 92 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationMethylene blue trihydrate: Does not have an individual approval but may be used under an appropriate group standard
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards
SYMPTOMS: Symptoms of exposure to this compound via ingestion include nausea, vomiting, diarrhea and dysuria. Ingestion of large amounts may cause hemolytic anemia. This compound causes skin irritation and severe eye irritation. Eye contact may result in corneal and conjunctival injury, stinging sensation, epiphora and, rarely, transient spasm of accommodation and blue coloration of the vitreous humor. Intravenous exposure to large amounts may cause nausea, abdominal pain, chest pain, headache, dizziness, mental confusion and profuse sweating. Subcutaneous exposure may lead to necrotic abscesses. Intrathecal injection may cause quadriplegia.
Hazards Summary
A skin and severe eye irritant; Toxic by ingestion (nausea, vomiting, diarrhea, dysuria, and hemolytic anemia from large doses); Repeated-dose oral studies of rats and mice demonstrated methemoglobinemia and a regenerative Heinz body anemia with secondary organ injury; Some evidence of carcinogenicity in male rats and mice, equivocal evidence in female mice, and no evidence in female rats; [NTP] A skin and strong eye irritant; Harmful by ingestion; Targets the blood, CNS, and eyes; May induce methemoglobinemia; [Sigma-Aldrich MSDS] See Methylene blue.
Chemie und Industrie
Verwendung und Herstellung
Uses
Used as a bacteriological stain, redox colorimetric agent, and in medicine (antimethemoglobinic); [Merck Index] Used to dye cotton and wool; [NTP]
Textiles (Printing, Dyeing, or Finishing) [Category: Industry]
Household ProductsInformation on 2 consumer products that contain Methylene blue in the following categories is provided:
Anwendungen
VerwendenMethylene Blue trihydrate finds many uses in biology and chemistry. It acts as a GCS inhibitor, biological stain and redox indicator. It inhibits tau filament formation. Further, it is reported to bind to the M2 subtype of muscarinic receptors in rat cardiac myocytes and thus exhibit antimuscarinic effects on IK, ACh and ICa. It also inhibits endothelium-dependent relaxation of isolated blood vessels.
Darstellung
synthetischeMethylene blue is synthesized commercially by oxidation of N,N-dimethyl-phenylenediamine with sodium dichromate (Na2Cr2O7) in the presence of sodium thiosulfate (Na2S2O3), followed by further oxidation in the presence of N,N-dimethylaniline (NTP, 2008). Methylene blue hydrochloride is isolated by addition of 30% hydrochloric acid and of a saturated common salt solution to the dye solution; after filtration, the product is washed with a 2% common salt solution. Instead of sodium dichromate, manganese dioxide, and catalytic amounts of copper sulfate can be used for the oxidation (Berneth, 2008). Methylene blue of high purity can be obtained by chloroform extraction of impurities from solutions of raw dye in borate buffer at pH 9.5–10, followed by acidification of the aqueous solution and isolation of the dye (Berneth, 2008).IARC Monographs
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