Methylene blue (CHEM016132)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:15:57 UTC
Update Date2016-11-09 01:15:20 UTC
Accession NumberCHEM016132
Identification
Common NameMethylene blue
ClassSmall Molecule
DescriptionAn organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.
Contaminant Sources
  • IARC Carcinogens Group 3
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Azul de metilenoChEBI
Basic blue 9ChEBI
Bleu de methyleneChEBI
C.I. 52015ChEBI
Chlorure de methylthioniniumChEBI
Cloruro de metiltioninioChEBI
MethylenblauChEBI
Methylene blue anhydrousChEBI
Methylthioninii chloridumChEBI
Methylthioninium chlorideChEBI
Solvent blue 8ChEBI
Swiss blueChEBI
Methylene blue NMeSH
Blue, swissMeSH
Methylthionine chlorideMeSH
Blue 9, basicMeSH
ChromosmonMeSH
Blue N, methyleneMeSH
Urolene blueMeSH
Blue, uroleneMeSH
Blue, methyleneMeSH
N, Methylene blueMeSH
Methylene blueMeSH
Chemical FormulaC16H18ClN3S
Average Molecular Mass319.850 g/mol
Monoisotopic Mass319.091 g/mol
CAS Registry Number7220-79-3
IUPAC Name3,7-bis(dimethylamino)-5λ⁴-phenothiazin-5-ylium chloride
Traditional Name3,7-bis(dimethylamino)-5λ⁴-phenothiazin-5-ylium chloride
SMILES[Cl-].CN(C)C1=CC2=[S+]C3=C(C=CC(=C3)N(C)C)N=C2C=C1
InChI IdentifierInChI=1S/C16H18N3S.ClH/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;1H/q+1;/p-1
InChI KeyCXKWCBBOMKCUKX-UHFFFAOYSA-M
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
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic chloride salt
  • Organic salt
  • Organonitrogen compound
  • Amine
  • 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 Solubility0.03 g/LALOGPS
logP3.61ALOGPS
logP2.61ChemAxon
logS-4ALOGPS
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
Polarizability33.1 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-82aa9088a4bfe6b83c95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-82aa9088a4bfe6b83c95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0009000000-82aa9088a4bfe6b83c95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-2af416e8b34595f1b1bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-2af416e8b34595f1b1bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0009000000-2af416e8b34595f1b1bcSpectrum
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
DrugBank IDDB09241
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 LinkMethylene_blue
Chemspider IDNot Available
ChEBI ID6872
PubChem Compound ID6099
Kegg Compound IDC00220
YMDB IDNot Available
ECMDB IDM2MDB005409
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11145393
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3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11287762
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5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11427637
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12068762
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=12830064
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=12845393
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10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16054909
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=16380099
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=16464752
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=17499345
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=17597293
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=17645185
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=17692516
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18. https://www.ncbi.nlm.nih.gov/pubmed/?term=17826794
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=17941276
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=18873190
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=18980251
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=19189650
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=19193212
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=19212058
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=19277479
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=19562136
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=19596056
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=19746714
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=24788930
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=25150147
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=25285998
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=25356528
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=25440279
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=25441767
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=25499271
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=25613051
37. https://www.ncbi.nlm.nih.gov/pubmed/?term=25679473
38. https://www.ncbi.nlm.nih.gov/pubmed/?term=25687361
39. https://www.ncbi.nlm.nih.gov/pubmed/?term=25707443
40. https://www.ncbi.nlm.nih.gov/pubmed/?term=25791029
41. https://www.ncbi.nlm.nih.gov/pubmed/?term=25913699
42. https://www.ncbi.nlm.nih.gov/pubmed/?term=26165999
43. https://www.ncbi.nlm.nih.gov/pubmed/?term=26192785
44. https://www.ncbi.nlm.nih.gov/pubmed/?term=26213475
45. https://www.ncbi.nlm.nih.gov/pubmed/?term=26221301
46. https://www.ncbi.nlm.nih.gov/pubmed/?term=26310944
47. https://www.ncbi.nlm.nih.gov/pubmed/?term=26463954
48. https://www.ncbi.nlm.nih.gov/pubmed/?term=26572462