Trimethyldiaminophenazathonium Chloride

Modify Date: 2026-07-01 09:12:45

Trimethyldiaminophenazathonium Chloride Structure
Trimethyldiaminophenazathonium Chloride structure
Common Name Trimethyldiaminophenazathonium Chloride
CAS Number 531-55-5 Molecular Weight 305.826
Density N/A Boiling Point N/A
Molecular Formula C15H16ClN3S Melting Point 205-210 °C (dec.)(lit.)
MSDS Chinese USA Flash Point N/A

 Use of Trimethyldiaminophenazathonium Chloride


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].

 Names

Name azure B
Synonym More Synonyms

 Trimethyldiaminophenazathonium Chloride 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
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
InChIKey DNDJEIWCTMMZBX-UHFFFAOYSA-N
SMILES CNc1ccc2nc3ccc(=[N+](C)C)cc-3sc2c1.[Cl-]

 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

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Trimethyldiaminophenazathonium Chloride Structure

Trimethyldiamin...

CAS#:531-55-5

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Literature: Materials Research Bulletin, , vol. 49, # 1 p. 544 - 551

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Trimethyldiaminophenazathonium Chloride Structure

Trimethyldiamin...

CAS#:531-55-5

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Literature: Chemische Berichte, , vol. 39, p. 1408 Chemische Berichte, , vol. 39, p. 1808 Justus Liebigs Annalen der Chemie, , vol. 230, p. 169,170 Chemische Berichte, , vol. 39, p. 1808

~%

Trimethyldiaminophenazathonium Chloride Structure

Trimethyldiamin...

CAS#:531-55-5

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Literature: Justus Liebigs Annalen der Chemie, , vol. 230, p. 169,170 Chemische Berichte, , vol. 39, p. 1808

~%

Trimethyldiaminophenazathonium Chloride Structure

Trimethyldiamin...

CAS#:531-55-5

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Literature: Chemische Berichte, , vol. 63, p. 1341,1346

 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%

 Articles33

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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.

Bioorg. Med. Chem. 19 , 5147-54, (2011)

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 Trimethyldiaminophenazathonium ChlorideBioassay

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Name: Displacement of Thioflavin S from synthetic Tau 2N4R aggregate by fluorescence assay ...
Source: ChEMBL
Target: N/A
External Id: CHEMBL1820217
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Source: ChEMBL
Target: N/A
External Id: CHEMBL1820216
Name: Inhibition of amyloid beta (1-42) aggregation (unknown origin) after 24 hrs by thiofl...
Source: ChEMBL
Target: Amyloid-beta precursor protein
External Id: CHEMBL3368553
Name: NCI human tumor cell line growth inhibition assay. Data for the MCF7 Non-Small Cell L...
Source: DTP/NCI
Target: N/A
External Id: MCF7_OneDose
Name: Inhibition of His-tagged human brain tau 3R MBD aggregation after 16 hrs by thioflavi...
Source: ChEMBL
Target: Microtubule-associated protein tau
External Id: CHEMBL3368556
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Source: DTP/NCI
Target: N/A
External Id: IGROV1_OneDose
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 Synonyms

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
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