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Key Documents

M9140

Sigma-Aldrich

Methylene blue

Dye content, ≥82%, certified by the Biological Stain Commission, powder

Synonym(s):

Basic Blue 9, 3,7-bis(Dimethylamino)phenazathionium chloride, Tetramethylthionine chloride

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About This Item

Empirical Formula (Hill Notation):
C16H18ClN3S · xH2O
CAS Number:
Molecular Weight:
319.85 (anhydrous basis)
Colour Index Number:
52015
Beilstein:
3599847
EC Number:
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.47

product name

Methylene blue, certified by the Biological Stain Commission

grade

certified by the Biological Stain Commission

Quality Level

form

powder

composition

Dye content, ≥82%

technique(s)

microbe id | staining: suitable

color

dark green

solubility

H2O: 4mg/4ml

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

CN(C)C1=CC=C2C(SC(C3=N2)=CC(C=C3)=[N+](C)C)=C1.[H]O[H].[Cl-]

InChI

1S/C16H18N3S.ClH.H2O/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;1H2/q+1;;/p-1

InChI key

WQVSELLRAGBDLX-UHFFFAOYSA-M

Gene Information

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General description

Methylene blue is a compound that occurs as crystals or crystalline powder, having a bronze-like luster. It is soluble in water, chloroform and partially soluble in alcohol. It is a photoactive dye, which is a member of phenothiazine family.

Application

Methylene blue has been used:
  • to stain vaginal cells
  • for the preparation of protein aqueous ink
  • to evaluate cell survival by staining

Biochem/physiol Actions

Methylene blue is used as a bacteriologic stain or dye and indicator. It mediates the inactivation of enveloped viruses in plasma, when exposed to visible light. It is an inhibitor of nitric oxide synthase and guanylate cyclase. It also plays a key role in medicine as an antimalarial agent, reducing agent in methemoglobinemia and inducer of apoptosis in cancer cells.

Suitability

Certified for use in Mallory′s phloxine-methylene blue stain; Levine & Black stain for bacteria in milk; Wright stain for blood smears.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Methylene blue: revisited
Ginimuge PR and Jyothi SD
Journal of Anaesthesiology, Clinical Pharmacology, 26(4), 517-517 (2010)
RNA determinants of translational operator recognition by the DNA polymerases of bacteriophages T4 and RB69.
Petrov VM and Karam JD
Nucleic Acids Research, 30, 3341-3341 (2002)
Transfusion Medicine and Hemostasis: Clinical and Laboratory Aspects (2008)
DJ-1 deficiency triggers microglia sensitivity to dopamine toward a pro-inflammatory phenotype that is attenuated by rasagiline
Trudler D, et al.
Journal of Neurochemistry, 129(3) (2014)
Amniotic fluid stem cells prevent follicle atresia and rescue fertility of mice with premature ovarian failure induced by chemotherapy.
Xiao GY
PLoS ONE, 9, e106538-e106538 (2014)

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