Toluidine blue (CHEM019954)

Record Information
Version1.0
Creation Date2016-05-22 06:39:16 UTC
Update Date2026-04-17 19:43:13 UTC
Accession NumberCHEM019954
Identification
Common NameToluidine blue
ClassSmall Molecule
Description
An organic chloride salt having 3-amino-7-(dimethylamino)-2-methylphenothiazin-5-ium (tolonium) as the counterion. It is a blue nuclear counterstain that can be used to demonstrate Nissl substance and is also useful for staining mast cell granules, both in metachromatic and orthochromatic techniques.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Amino-7-(dimethylamino)-2-(methylphenazathionium) chlorideChEBI
Basic blue 17ChEBI
Blutene chlorideChEBI
C.I. 52040ChEBI
C.I. 925ChEBI
C.I. basic blue 17ChEBI
Chlorure de toloniumChEBI
Cloruro de tolonioChEBI
Dimethyltoluthionine chlorideChEBI
Toloni chloridumChEBI
Tolonii chloridumChEBI
Toluidene blue O chlorideChEBI
ToluidinblauChEBI
Toluidine blueChEBI
Toluidine blue OChEBI
Chemical FormulaC15H16ClN3S
Average Molecular Mass305.820 g/mol
Monoisotopic Mass305.075 g/mol
CAS Registry Number92-31-9
IUPAC Name3-amino-7-(dimethylamino)-2-methyl-5λ⁴-phenothiazin-5-ylium chloride
Traditional Name3-amino-7-(dimethylamino)-2-methyl-5λ⁴-phenothiazin-5-ylium chloride
SMILES[Cl-].CN(C)C1=CC2=[S+]C3=C(C=C(C)C(N)=C3)N=C2C=C1
InChI IdentifierInChI=1S/C15H16N3S.ClH/c1-9-6-13-15(8-11(9)16)19-14-7-10(18(2)3)4-5-12(14)17-13;/h4-8H,16H2,1-3H3;1H/q+1;/p-1
InChI KeyHNONEKILPDHFOL-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
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary amine
  • Azacycle
  • Amine
  • Organic salt
  • Organic chloride salt
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Primary amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • 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 Solubility0.04 g/LALOGPS
logP3.24ALOGPS
logP2.19ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)19.81ChemAxon
pKa (Strongest Basic)2.73ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area42.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity82.29 m³·mol⁻¹ChemAxon
Polarizability31.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
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 IDNot Available
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 LinkTolonium_chloride
Chemspider IDNot Available
ChEBI ID87647
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23884903
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24981641
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25463317
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25670474
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25752750
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25910445
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=25972050
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26055566