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Methylene blue

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Methylene blue

Methylthioninium chloride, commonly called methylene blue, is a salt used as a dye and as a medication. As a medication, it is mainly used to treat methemoglobinemia. It has previously been used for treating cyanide poisoning and urinary tract infections, but this use is no longer recommended. It has also been used to treat cases of malaria for over a century. Methylene blue is typically given by injection into a vein. Common side effects include headache, nausea, and vomiting. Methylene blue was first prepared in 1876, by Heinrich Caro. It is on the World Health Organization's List of Essential Medicines.

Infobox

Trade names
Urelene blue, Provayblue, Proveblue, others
Other names
CI 52015, basic blue 9
AHFS/Drugs.com
Monograph
License data
mw- US DailyMed: Provayblue
Pregnancycategory
AU: D
Routes ofadministration
By mouth, intravenous
ATC code
V03AB17 (WHO) V04CG05 (WHO)
Legal status
US: ℞-only EU: Rx-only
Elimination half-life
5–24 hours (IVTooltip intravenous therapy)
Excretion
RenalIn rats: 18%(POTooltip Oral administration), 28% (IV)
CAS Number
61-73-4 Y
PubChem CID
6099
DrugBank
DB09241 Y
ChemSpider
5874 Y
UNII
8NAP7826UB
KEGG
D10537C00220
ChEBI
CHEBI:6872 Y
ChEMBL
ChEMBL405110 Y
CompTox Dashboard (EPA)
DTXSID0023296
ECHA InfoCard
100.000.469
Formula
C16H18ClN3S
Molar mass
319.85 g·mol−1
3D model (JSmol)
Interactive image

Tables

· Side effects
Hypertension Precordial pain
Hypertension Precordial pain
Cardiovascular
Hypertension Precordial pain
Central nervous system
Dizziness Mental confusion Headache Fever
Dermatologic
Staining of skin Injection site necrosis (SC)
Gastrointestinal
Fecal discoloration Nausea Vomiting Abdominal pain
Genito-urinary
Discoloration of urine (doses over 80 μg) Bladder irritation
Hematologic
Anemia
Cardiovascular
Central nervous system
Dermatologic
Gastrointestinal
Genito-urinary
Hematologic
Hypertension Precordial pain
Dizziness Mental confusion Headache Fever
Staining of skin Injection site necrosis (SC)
Fecal discoloration Nausea Vomiting Abdominal pain
Discoloration of urine (doses over 80 μg) Bladder irritation
Anemia
· Chemistry › Light absorption properties
MB+ (solution)
MB+ (solution)
Species
MB+ (solution)
Absorption peak
664
Extinction coefficient (dm3/mol·cm)
95000
MBH2+ (solution)
MBH2+ (solution)
Species
MBH2+ (solution)
Absorption peak
741
Extinction coefficient (dm3/mol·cm)
76000
(MB+)2 (solution)
(MB+)2 (solution)
Species
(MB+)2 (solution)
Absorption peak
605
Extinction coefficient (dm3/mol·cm)
132000
(MB+)3 (solution)
(MB+)3 (solution)
Species
(MB+)3 (solution)
Absorption peak
580
Extinction coefficient (dm3/mol·cm)
110000
MB+ (adsorbed on clay)
MB+ (adsorbed on clay)
Species
MB+ (adsorbed on clay)
Absorption peak
673
Extinction coefficient (dm3/mol·cm)
116000
MBH2+ (adsorbed on clay)
MBH2+ (adsorbed on clay)
Species
MBH2+ (adsorbed on clay)
Absorption peak
763
Extinction coefficient (dm3/mol·cm)
86000
(MB+)2 (adsorbed on clay)
(MB+)2 (adsorbed on clay)
Species
(MB+)2 (adsorbed on clay)
Absorption peak
596
Extinction coefficient (dm3/mol·cm)
80000
(MB+)3 (adsorbed on clay)
(MB+)3 (adsorbed on clay)
Species
(MB+)3 (adsorbed on clay)
Absorption peak
570
Extinction coefficient (dm3/mol·cm)
114000
Species
Absorption peak
Extinction coefficient (dm3/mol·cm)
MB+ (solution)
664
95000
MBH2+ (solution)
741
76000
(MB+)2 (solution)
605
132000
(MB+)3 (solution)
580
110000
MB+ (adsorbed on clay)
673
116000
MBH2+ (adsorbed on clay)
763
86000
(MB+)2 (adsorbed on clay)
596
80000
(MB+)3 (adsorbed on clay)
570
114000

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