Methylthioninium (CHEM043440)

Record Information
Version1.0
Creation Date2016-06-03 10:54:25 UTC
Update Date2026-08-19 16:02:59 UTC
Accession NumberCHEM043440
Identification
Common NameMethylthioninium
ClassSmall 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 TypeNot Available
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Methylene blue cationChEBI
Methylene blueMeSH
Blue, swissMeSH
Blue 9, basicMeSH
Urolene blueMeSH
Blue, methyleneMeSH
Methylthioninium chlorideMeSH
Blue, uroleneMeSH
ChromosmonMeSH
Methylthionine chlorideMeSH
Swiss blueMeSH
Basic blue 9MeSH
Methylene blue NMeSH
Blue N, methyleneMeSH
Chemical FormulaC16H18N3S
Average Molecular Mass284.399 g/mol
Monoisotopic Mass284.122 g/mol
CAS Registry Number61-73-4
IUPAC Name3,7-bis(dimethylamino)-5λ⁴-phenothiazin-5-ylium
Traditional Name3,7-bis(dimethylamino)-5λ⁴-phenothiazin-5-ylium
SMILESCN(C)C1=CC2=[S+]C3=CC(=CC=C3N=C2C=C1)N(C)C
InChI IdentifierInChI=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 KeyRBTBFTRPCNLSDE-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).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassNot Available
Direct ParentBenzothiazines
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP2.8ALOGPS
logP2.61ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)2.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area19.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity86.98 m³·mol⁻¹ChemAxon
Polarizability33.11 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB08167
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID43830
PubChem Compound ID4139
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References