Methylene Blue

CAS

61-73-4

Catalog Number

ACM61734

Category

Inhibitors

Molecular Weight

319.85

Molecular Formula

C16H18ClN3S

MSDS COA Spec Sheet

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Specification

Description

Methylene blue (Basic Blue 9) is a guanylyl cyclase (sGC), monoamine oxidase A (MAO-A) and NO synthase (NOS) inhibitor. Methylene blue is a vasopressor and is often used as a dye in several medical procedures. Methylene blue through the nitric oxide syntase/guanylate cyclase signalling pathway to reduce prepulse inhibition. Methylene blue is a REDOX cycling compound and able to cross the blood-brain barrier. Methylene blue is a Tau aggregation inhibitor. Methylene blue reduces cerebral edema, attenuated microglial activation and reduced neuroinflammation.

Synonyms

Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride;SWISS BLUE;Evan’s Blue;Chromosmon;CI BASIC BLUE 9

Canonical SMILES

CN(C)C1=CC=C2C(SC(C(C=C/3)=N2)=CC3=[N+](C)/C)=C1.[Cl-]

Melting Point

190ºC (dec.)(lit.)

Flash Point

45ºC

Density

Appearance

Green fine crystalline powder

Storage

4°C, sealed storage, away from moisture and light*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)

Hazard Codes

Hazard Statements

HS Code

2934300000

LogP

-0.49710

PSA

47.38

RIDADR

UN 1993 3/PG 3

Safety Description

26-39-36

Shipping

Can be shipped at room temperature, where not in use may vary.

Storage Conditions

Store at RT

Supplemental Hazard Statements

H226

Symbol

GHS02

WGK Germany

The Applications of Methylene Blue and Its Photodegradation Pathways

Khan, Idrees, et al. Water, 2022, 14(2). 242.

Methylene blue (MB) is a well-known cationic primary thiazine dye and one of the most consumed materials in the dye industry. In addition, methylene blue is an attractive molecule with many potential applications in biomedical applications, such as an effective therapeutic agent for anemia, malaria, and Barrett's esophagus, as well as photodynamic therapy for cancer.
Photodegradation pathways of methylene blue
· Considering the toxicity of methylene blue, its removal from wastewater through photocatalytic degradation technology is an effective way. Effective photocatalyst systems that have been developed include ZnO-NPs catalyst, Fe2O3/graphene/CuO photocatalyst, etc.
· The photodegradation steps of MB can be divided into: (1) demethylation; (2) MB central aromatic ring cleavage, followed by lateral aromatic ring cleavage; (3) fragments generated in the first two steps are converted into intermediate substances; (4) intermediates are converted into final products such as CO2, H2O, ammonium ions and sulfate ions.

Preparation and Application of Methylene Blue Nanoparticles and Microparticles

Dong-Jin Lim. Polymers, 2021, 13(22), 3955.

Due to the hydrophilic nature of methylene blue (MB), the efficacy of MB as a photosensitizer in photodynamic therapy (PDT) is limited to a certain extent. The development of efficient MB-embedded nanoparticles or microparticles can effectively improve the clinical efficacy of PDT and further be used to treat cancer and infectious diseases.
Preparation of MB nanoparticles and microparticles
· Methylene blue in polymeric nano- and microparticles: MB can be encapsulated in polymeric nano/microparticles, such as polyacrylamide nanoparticles, poly(N-isopropylacrylamide) (PNIPAM) microgels, and polymeric lipids wait.
· Methylene blue in inorganic nano- and microparticles: MB can be incorporated into a variety of inorganic nano- and microparticles, such as silica nanoparticles, organically modified silicate (ORMOSIL) nanoparticles, and gold nanoparticles.
· Methylene blue in inorganic polymer composites: More types of MB functional materials can be realized through inorganic polymer composites, such as MB trapped in silicone elastomers with nanogold.

Methylene Blue-Mediated Antibacterial Photodynamic Therapy

Cecatto, Rebeca Boltes, et al. Photodiagnosis and Photodynamic Therapy, 2020, 31, 101828.

Photodynamic therapy (PDT) is a therapy mediated by visible light, photosensitizer (PS), and oxygen. Methylene blue (MB) is a photosensitizer (PS) belonging to the phenothiazine class, which consists of two benzene rings connected to a nitrogen atom and a sulfur atom. MB is less toxic when applied to humans, and due to its lipophilicity, it has greater cellular distribution and the ability to penetrate blood cells, therefore, it provides a possible alternative for the clinical application of aPDT.
Antimicrobial PDT (aPDT) with methylene blue as photosensitizer
· The aPDT with MB for the treatment of human clinical infections are available: onychomycosis, oral candidiasis, and diabetic foot infectious ulcer treatments.
· Regarding the MB and light parameters, the pre-irradiation times ranged from 1 min to 5 min; the concentrations ranged from 0.0003 to 0.06 molar; lasers, LED, and lamps were used, always encompassing the red wavelength, being resonant with MB; the irradiances ranged from 50 mW/cm2 to 750 mW/cm2; the radiant exposures ranged from 6 to 18 J/cm2, and the irradiation times ranged from 8 seconds to 10 minutes.

What is the molecular formula of Methylene Blue?

The molecular formula of Methylene Blue is C16H18ClN3S.

When was Methylene Blue created and last modified?

Methylene Blue was created on March 26, 2005, and last modified on December 23, 2023.

What are some synonyms for Methylene Blue?

Some synonyms for Methylene Blue include Basic blue 9, Methylthioninium chloride, and Solvent blue 8.

What is the molecular weight of Methylene Blue?

The molecular weight of Methylene Blue is 319.9 g/mol.

What is the description and role of Methylene Blue?

Methylene Blue is an organic chloride salt with various properties such as being an antioxidant, antimalarial, antidepressant, and cardioprotective agent. It also acts as a monoamine oxidase inhibitor, acid-base indicator, fluorochrome, cholinesterase inhibitor, and more.

How is Methylene Blue used in medical treatments?

The intravenous form of Methylene Blue is approved by the FDA for the treatment of acquired methemoglobinemia. It has also been used historically to treat malaria.

What are some other identifiers for Methylene Blue?

Other identifiers for Methylene Blue include CAS numbers 61-73-4, 7220-79-3, and 97130-83-1.

What is the IUPAC name of Methylene Blue?

The IUPAC name of Methylene Blue is [7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium; chloride.

How is Methylene Blue used in bacteriology?

Methylene Blue is used as a bacteriologic stain and an indicator in solutions in water or alcohol.

What is the investigational drug being developed based on Methylene Blue?

Methylthioninium chloride, also known as Methylene Blue and proposed trade name Rember, is an investigational drug being developed for the treatment of Alzheimer's disease by inhibiting Tau protein aggregation.

What is the role of Methylene Blue as an inhibitor?

Methylene Blue has a role as an EC 1.4.3.4 (monoamine oxidase) inhibitor, an EC 3.1.1.8 (cholinesterase) inhibitor, and an EC 4.6.1.2 (guanylate cyclase) inhibitor.

How is Methylene Blue used as a dye?

Methylene Blue is commonly used as a dye that also exhibits antioxidant, antimalarial, antidepressant, and cardioprotective properties.

What is the chemical safety information for Methylene Blue?

The Laboratory Chemical Safety Summary (LCSS) datasheet provides information on the chemical safety of Methylene Blue.

What is the parent compound of Methylene Blue?

The parent compound of Methylene Blue is CID 4139 (Methylene blue cation).

What are some component compounds of Methylene Blue?

Component compounds of Methylene Blue include CID 313 (Hydrochloric Acid) and CID 4139 (Methylene blue cation).

How is intravenous Methylene Blue approved for medical use?

The intravenous form of Methylene Blue is approved by the FDA for the treatment of pediatric and adult patients with acquired methemoglobinemia.

How is Methylene Blue used in the treatment of Alzheimer's disease?

Methylene Blue, also known as Methylthioninium chloride, is being developed as an investigational drug to inhibit Tau protein aggregation, which is of potential interest for the treatment of patients with Alzheimer's disease.

Downstream Synthesis Route 1

61-73-4

1236208-20-0

Reference: [1]Current Patent Assignee: TAURX PHARMACEUTICALS LTD - WO2012/107706, 2012, A1

* For details of the synthesis route, please refer to the original source to ensure accuracy.