Methylene Blue trihydrate - Biological Stain, Purifed, ≥90%(HPLC) , CAS No.7220-79-3

CAS: 7220-79-3 Cat. No.: M102717 Summenformel: C₁₆H₁₈ClN₃S·3H₂O Molekulargewicht: 373.9 Beilstein Registry Number: 3599847 EG-Nummer: 615-731-6

GRADE & PURITY Biological Stain, Purifed, ≥90%(HPLC)

Synonyms

[7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium;chloride;trihydrate | METHYLENE BLUE [IARC] | Methylene blue (USP) | methylthioninium chloride trihydrate | Basic Blue 9 trihydrate | DTXSID0025600 | AKOS005167162 | E76384 | C16H18ClN3S | METHYLTH

Storage

Room temperature

Shipped In

Normal

Übersicht

Methylene Blue acts as a GCS (guanylyl cyclase) inhibitor, biological stain and redox indicator. Methylene Blue inhibits tau filament formation. Additionally, Methylene Blue is also reported to inhibit NOSs (nitric oxide synthase). Methylene Blue is widely used to inhibit cGMP-mediated processes. Methylene Blue has been observed to dose-dependently induce cytotoxicity in U-373 MG human astrocytoma and SK-N-MC human neuroblastoma cells. Furthermore Methylene Blue 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. Methylene Blue has also been reported to inhibit endothelium-dependent relaxation of isolated blood vessels.
An inhibitor of cGMP-mediated processes and guanylyl cyclase, a useful stain, and a redox indicator

Specifications

Synonyme

[7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium;chloride;trihydrate | METHYLENE BLUE [IARC] | Methylene blue (USP) | methylthioninium chloride trihydrate | Basic Blue 9 trihydrate | DTXSID0025600 | AKOS005167162 | E76384 | C16H18ClN3S | METHYLTH

Spezifikationen & Reinheit

Biological Stain, Purifed, ≥90%(HPLC)

Storage

Room temperature

Verschickt in

Normal

Note

Biological Stain, Purifed

Aktionsart

INHIBITOR

Reinheit

≥90%(HPLC)

Namen und Kennungen

Pubchem Sid

488187373

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488187373

Kanonisches Lächeln

CN(C)C1=CC2=C(C=C1)N=C3C=CC(=[N+](C)C)C=C3S2.O.O.O.[Cl-]

IUPAC Name

[7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium;chloride;trihydrate

InChIKey

XQAXGZLFSSPBMK-UHFFFAOYSA-M

INCHI

1S/C16H18N3S.ClH.3H2O/c1-18(2)11-5-7-13-15(9-11)20-16-10-12(19(3)4)6-8-14(16)17-13;;;;/h5-10H,1-4H3;1H;3*1H2/q+1;;;;/p-1

Isomere SMILES

CN(C)C1=CC2=C(C=C1)N=C3C=CC(=[N+](C)C)C=C3S2.O.O.O.[Cl-]

WGK Deutschland

2

Molekulargewicht

373.9

Beilstein

3599847

Reaxy-Rn

16692608

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=16692608&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Klasse Benzothiazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Klasse: Benzothiazines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzothiazines
• Alternative Parents: Dialkylarylamines Benzenoids Secondary ketimines Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Organic oxides Organic chloride salts Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Benzothiazine - Tertiary aliphatic/aromatic amine - Dialkylarylamine - Benzenoid - Secondary ketimine - Heteroaromatic compound - Tertiary amine - Azacycle - Organic chloride salt - Organic oxide - Organic salt - Organopnictogen compound - Organic oxygen compound - Amine - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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Caco-2 (12174 Activities)

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Lymphoblastoid cell (5959 Activities)

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HIF1A Tchem Hypoxia-inducible factor 1 alpha (6027 Activities)

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HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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SMN1 Tchem Survival motor neuron protein (34246 Activities)

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RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Löslichkeit: Soluble in water (50 mg/ml), ethanol (70 mg/ml), alcohol, and chloroform. Insoluble in ether.
• Schmelzpunkt (°C): 235°C
• Molekulargewicht: 373.900 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 373.123 Da
• Monoisotopic Mass: 373.123 Da
• Topological Polar Surface Area: 46.900 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 483.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 5

XLogP3