Trimethyldiaminophenazathonium Chloride

Names

[ CAS No. ]:
531-55-5

[ Name ]:
Trimethyldiaminophenazathonium Chloride

[Synonym ]:
Trimethylthionine chloride
N,N-Dimethyl-7-(methylamino)-3H-phenothiazin-3-iminium chloride
Methyleneazure
3-Methylamino-7-dimethylaminophenazathonium Chloride
N,N,N'-Trimethylthionin
EINECS 208-511-2
3-(Dimethylamino)-7-(methylamino)phenothiazin-5-ium chloride
Methanaminium, N-methyl-N-[7-(methylamino)-3H-phenothiazin-3-ylidene]-, chloride (1:1)
Trimethyldiaminophenazathonium Chloride
Azure B eosinate
Azure B,Certified
Azure I
Phenothiazinium, 3-(dimethylamino)-7-(methylamino)-, chloride (1:1)
Phenothiazin-5-ium, 3- (dimethylamino)-7-(methylamino)-, chloride
MFCD00011935
AZUR I
dimethyl-[7-(methylamino)phenothiazin-3-ylidene]azanium,chloride
Azure B

Biological Activity

[Description]:

Azure B is a cationic dye and the major metabolite of Methylene blue. Azure B is used in making Azure eosin stains for blood smear staining. Azure B is a high-potency, selective and reversible inhibitor of monoamine oxidases (MAO)-A, with IC50s of 11 and 968 nM for recombinant human MAO-A and MAO-B, respectively. Azure B possesses significant antidepressant-like effects[1][2].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase

Research Areas >> Neurological Disease

[In Vivo]

Azure B (4-30 mg/kg; i.p.; once) decreases immobility in the forced swim test (FST)[1].

[References]

[1]. Löhr W,et al. The azure dyes: their purification and physicochemical properties. II. Purification of azure B. Stain Technol. 1975 May;50(3):149-56.

[2]. Delport A, et al. Azure B and a synthetic structural analogue of methylene blue, ethylthioninium chloride, present with antidepressant-like properties. Life Sci. 2014 Nov 11;117(2):56-66.

Chemical & Physical Properties

[ Melting Point ]:
205-210 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₅H₁₆ClN₃S

[ Molecular Weight ]:
305.826

[ Exact Mass ]:
305.075348

[ PSA ]:
56.17000

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SO5550000

CHEMICAL NAME :: 3H-Phenothiazine, 3-(dimethylamino)-7-(methylimino)-, hydrochloride

CAS REGISTRY NUMBER :: 531-55-5

LAST UPDATED :: 199504

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C15-H16-N3-S.Cl

MOLECULAR WEIGHT :: 305.85

WISWESSER LINE NOTATION :: T C666 BS EY INJ EUN1 MN1&1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 65 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 20 umol/L/5H (Continuous)

REFERENCE :: ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 1,27,1979 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - T1407 No. of Facilities: 150 (estimated) No. of Industries: 2 No. of Occupations: 2 No. of Employees: 664 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - T1407 No. of Facilities: 101 (estimated) No. of Industries: 2 No. of Occupations: 2 No. of Employees: 3055 (estimated) No. of Female Employees: 2122 (estimated)

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
SO5550000

[ HS Code ]:
2934300000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934300000

[ Summary ]:
2934300000. other compounds containing in the structure a phenothiazine ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Microbes Infect. 17(3) , 184-94, (2015)

In malaria, the evidence concerning the nucleotide-binding, oligomerization domain (NOD) 2 (NOD2) receptor is fragmented and the stimuli that might activate NOD2 are not well characterized. We investi...

Azure B and a synthetic structural analogue of methylene blue, ethylthioninium chloride, present with antidepressant-like properties.

Life Sci. 117(2) , 56-66, (2015)

The phenothiazinium compound, methylene blue (MB), possesses diverse pharmacological actions and is attracting attention for the treatment of bipolar disorder and Alzheimer's disease. MB acts on both ...

Ligand polarizability contributes to tau fibril binding affinity.

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Whole brain imaging of tau-bearing neurofibrillary lesions has the potential to improve the premortem diagnosis and staging of Alzheimer's disease. Diverse compounds with high affinity for tau aggrega...