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Details

Stereochemistry ACHIRAL
Molecular Formula C16H18N3S.Cl
Molecular Weight 319.852
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLENE BLUE ANHYDROUS

SMILES

[Cl-].CN(C)C1=CC2=[S+]C3=C(C=CC(=C3)N(C)C)N=C2C=C1

InChI

InChIKey=CXKWCBBOMKCUKX-UHFFFAOYSA-M
InChI=1S/C16H18N3S.ClH/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/q+1;/p-1

HIDE SMILES / InChI

Description

Methylene blue, also known as methylthioninium chloride, is a medication from WHO's list of essential medicines. Upon administration, methylene blue is converted to leukomethylene blue by erythrocyte methemoblobin reductase in the presence of NADPH. Leukomethylene blue than reduces methemoglobin to oxyhemoglobin, thus restoring oxygen carrying capacity of the blood. Methylene blue is also used as a dye for various diagnostic procedures, for treatment of ifosfamide toxicity and for in vitro staining. Historically, it was used as a photosensitizer for photodynamic therapy for topical treatment of dermatologic or mucocutaneous infections, as an antidote for cyanide poisoning, but these applications are no longer approved. Methylene blue is investigated in clinical trials for treatment of septic shock and Alzheimer's disease.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
5.3 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
METHYLENE BLUE
Primary
METHYLENE BLUE
Diagnostic
METHYLENE BLUE
Primary
METHYLENE BLUE
Primary
Unknown
Preventing
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
2917 ng/mL
2 mg/kg single, intravenous
METHYLENE BLUE plasma
Homo sapiens
8 μM
100 mg single, intravenous
METHYLENE BLUE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
13977 ng × h/mL
2 mg/kg single, intravenous
METHYLENE BLUE plasma
Homo sapiens
134 μM × min
100 mg single, intravenous
METHYLENE BLUE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
24 h
2 mg/kg single, intravenous
METHYLENE BLUE plasma
Homo sapiens
6.6 h
100 mg single, intravenous
METHYLENE BLUE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
2 mg/kg single, intravenous
METHYLENE BLUE plasma
Homo sapiens

Doses

AEs

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
Main route of adminitration is intravenous, 1-2 mg/kg by slow IV injection. Inject slowly over several minutes (usually 3–10 minutes). Historically was also administered orally, but oral preparations are no longer commercially available in US. As a photosensitizer is administered topically. For a diagnostic purposes is administered by local instillation or injection.
Route of Administration: Other
In Vitro Use Guide
Suspension of erytrocytes from acid/citrate/dextrose-treated blood were incubabed on air with 0.5M M-sodium nitrite solution in isoosmotic saline. The erytrocytes were separated by centrifugation, washed, and incubated at pH 7.4 and 37°C with 10 mM glucose and 10 uM Methylene Blue. Samples were taken at defined intervals and hemolysed with 10 vol of ice-cold water, after that the content of mehtemoglobin, hemoglobins intermediate and oxyhemoglobin was estimated.