ContaminantDB: Toluidine blue

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

Record Information

Version

1.0

Creation Date

2016-05-22 06:39:16 UTC

Update Date

2016-11-09 01:16:06 UTC

Accession Number

CHEM019954

Identification

Common Name

Toluidine blue

Class

Small 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 Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Amino-7-(dimethylamino)-2-(methylphenazathionium) chloride	ChEBI
Basic blue 17	ChEBI
Blutene chloride	ChEBI
C.I. 52040	ChEBI
C.I. 925	ChEBI
C.I. basic blue 17	ChEBI
Chlorure de tolonium	ChEBI
Cloruro de tolonio	ChEBI
Dimethyltoluthionine chloride	ChEBI
Toloni chloridum	ChEBI
Tolonii chloridum	ChEBI
Toluidene blue O chloride	ChEBI
Toluidinblau	ChEBI
Toluidine blue	ChEBI
Toluidine blue O	ChEBI

Chemical Formula

C₁₅H₁₆ClN₃S

Average Molecular Mass

305.820 g/mol

Monoisotopic Mass

305.075 g/mol

CAS Registry Number

92-31-9

IUPAC Name

3-amino-7-(dimethylamino)-2-methyl-5λ⁴-phenothiazin-5-ylium chloride

Traditional Name

3-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 Identifier

InChI=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 Key

HNONEKILPDHFOL-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).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Not Available

Direct Parent

Benzothiazines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic chloride salt (CHEBI:87647 )

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	0.04 g/L	ALOGPS
logP	3.24	ALOGPS
logP	2.19	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	19.81	ChemAxon
pKa (Strongest Basic)	2.73	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.29 m³·mol⁻¹	ChemAxon
Polarizability	31.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0009000000-43456085b2c5f284e5a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0009000000-43456085b2c5f284e5a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0009000000-43456085b2c5f284e5a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-86587d7f2f988aa5854d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0009000000-86587d7f2f988aa5854d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0009000000-86587d7f2f988aa5854d	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

Not Available

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

Tolonium_chloride

Chemspider ID

Not Available

ChEBI ID

87647

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not 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

Toluidine blue (CHEM019954)

Structure for CHEM019954: Toluidine blue