ContaminantDB: Methylthioninium

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-06-03 10:54:25 UTC

Update Date

2016-11-09 01:22:55 UTC

Accession Number

CHEM043440

Identification

Common Name

Methylthioninium

Class

Small Molecule

Description

An organic cation that is phenothiazin-5-ium substituted by dimethylamino groups at positions 3 and 7. The chloride salt is the histological dye 'methylene blue'.

Contaminant Sources

STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Methylene blue cation	ChEBI
Methylene blue	MeSH
Blue, swiss	MeSH
Blue 9, basic	MeSH
Urolene blue	MeSH
Blue, methylene	MeSH
Methylthioninium chloride	MeSH
Blue, urolene	MeSH
Chromosmon	MeSH
Methylthionine chloride	MeSH
Swiss blue	MeSH
Basic blue 9	MeSH
Methylene blue N	MeSH
Blue N, methylene	MeSH

Chemical Formula

C₁₆H₁₈N₃S

Average Molecular Mass

284.399 g/mol

Monoisotopic Mass

284.122 g/mol

CAS Registry Number

61-73-4

IUPAC Name

3,7-bis(dimethylamino)-5λ⁴-phenothiazin-5-ylium

Traditional Name

3,7-bis(dimethylamino)-5λ⁴-phenothiazin-5-ylium

SMILES

CN(C)C1=CC2=[S+]C3=CC(=CC=C3N=C2C=C1)N(C)C

InChI Identifier

InChI=1S/C16H18N3S/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/q+1

InChI Key

RBTBFTRPCNLSDE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Not Available

Direct Parent

Benzothiazines

Alternative Parents

Substituents

Benzothiazine
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Benzenoid
Heteroaromatic compound
Secondary ketimine
Tertiary amine
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic cation (CHEBI:43830 )
a dye (CPD0-1625 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	2.8	ALOGPS
logP	2.61	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	2.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	19.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	86.98 m³·mol⁻¹	ChemAxon
Polarizability	33.11 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-2190000000-6b032702c13546a46e48	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0090000000-562c1559e4cf7d40a13c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0090000000-05faeb4f27f1a84c54a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0090000000-77b5d8e28d6335764623	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0090000000-c0e7ada3d60537137629	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0090000000-d93a9ae23e6746b4eb6f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-014i-0090000000-66627aab76bec0253023	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-a92629538289d6cd99d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-f2751c05dc8adb520cff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-3920000000-c45ca4c7c5c09dccd23f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-b12310fc26dd8a636522	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-69824464da9320b0582c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-4290000000-f2c04b211bf033b988cb	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB08167

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

43830

PubChem Compound ID

4139

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Methylthioninium (CHEM043440)

Structure for CHEM043440: Methylthioninium