Methylene Blue trihydrate

Names

[ Name ]:
Methylene Blue trihydrate

[Synonym ]:
Phenothiazinium, 3,7-bis(dimethylamino)-, chloride, hydrate (1:1:3)
BASIC BLUE 9 HYDRATE
METHYLENE BLUE TS
Methylene Blue trihy
MFCD00150008
EINECS 200-515-2
3,7-Bis(dimethylamino)phenothiazin-5-ium chloride hydrate (1:1:3)
3,7-bis(dimethylamino)phenothiazin-5-ium chloride hydrate(1:1:3)
METHYLENE BLUE HYDRATE
Methylene Blue
3,7-bis(dimethylamino)phenazathionium chloride trihydrate
Methylene Blue BB
3,7-Bis(dimethylamino)phenothiazin-5-ium chloride trihydrate

Biological Activity

[Description]:

Methylene blue trihydrate (C.I. Basic Blue 9 trihydrate) is a guanylyl cyclase (sGC), monoamine oxidase A (MAO-A) and NO synthase (NOS) inhibitor. Methylene blue trihydrate is a vasopressor and is often used as a dye in several medical procedures. Methylene blue trihydrate has antinociception, antimalarial, antidepressant and anxiolytic activity effects. Methylene Blue trihydrate has the potential for methemoglobinemias, neurodegenerative disorders and ifosfamide-induced encephalopathytreatment[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Immunology/Inflammation >> NO Synthase

Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> Guanylate Cyclase

[Target]

Guanylyl cyclase (sGC)[1]. Monoamine oxidase A (MAO-A)[1]. NO synthase (NOS)[1]

[In Vitro]

By acting as an alternative electron acceptor/donor Methylene blue restores mitochondrial function, improves neuronal energy production and inhibits the formation of superoxide[1]. Methylene blue inhibits cytochrome P450 (CYP) isozymes. Methylene blue is an odorless, water soluble, dark blue-green crystalline powder, which turns blue whenever mixed in solution. Methylene blue is a vasopressor that impacts the NO synthetic pathway by inhibiting inducible NOS and inhibiting the subsequent activation of sGC. In addition, by binding to the iron heme moiety of sGC and causing enzyme inhibition, Methylene blue blocks accumulation of cyclic GMP (cGMP), competing directly with NO in its ability to activate soluble guanylyl cyclase[3].

[In Vivo]

Methylene Blue (1, 5, and 25 μg/rat) significantly decreases sevoflurane minimum alveolar anesthetic concentration (MAC) and brain cyclic guanosine monophosphate (cGMP) content in a dose-dependent manner in male Sprague-Dawley rats (7-week-old, 200-250 g)[2]. Methylene blue is used as a dye in chromoendoscopy, and is sprayed onto the mucosa of the gastrointestinal tract in order to identify dysplasia, or pre-cancerous lesions[2]. Methylene blue is able to restore vascular tone, normalize mean arterial pressures (MAP), and reduce vasopressor usage[3].

[References]

[1]. Delport A, et al. Methylene blue and its analogues as antidepressant compounds. Metab Brain Dis. 2017 Oct;32(5):1357-1382.

[2]. Masaki E, et al. Methylene blue, a soluble guanylyl cyclase inhibitor, reduces the sevoflurane minimum alveolar anesthetic concentration and decreases the brain cyclic guanosine monophosphate content in rats. Anesth Analg. 1999 Aug;89(2):484-9.

[3]. McCartney SL, et al. Intraoperative vasoplegia: methylene blue to the rescue! Curr Opin Anaesthesiol. 2018 Feb;31(1):43-49.

Chemical & Physical Properties

[ Density]:
0.98 g/mL at 25 °C

[ Melting Point ]:
190 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₆H₂₄ClN₃O₃S

[ Molecular Weight ]:
373.898

[ Flash Point ]:
14 °C

[ Exact Mass ]:
373.122681

[ PSA ]:
75.07000

[ Storage condition ]:
Store at RT.

[ Stability ]:
Stable. Incompatible with bases, reducing agents, strong oxidizing agents.

[ Water Solubility ]:
4 g/100 mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SP5740000

CHEMICAL NAME :: Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride, trihydrate

CAS REGISTRY NUMBER :: 7220-79-3

LAST UPDATED :: 199712

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C16-H18-N3-S.Cl.3H2-O

MOLECULAR WEIGHT :: 373.94

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H319

[ Precautionary Statements ]:
P210-P280-P305 + P351 + P338-P337 + P313-P403 + P235

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S26-S36-S24/25-S16-S7

[ RIDADR ]:
UN 1170 3/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
SP5740000

[ Hazard Class ]:
6.1

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