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Details

Stereochemistry ACHIRAL
Molecular Formula C15H16N3S.Cl.H2O4S
Molecular Weight 403.904
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOLONIUM CHLORIDE SULFATE

SMILES

[Cl-].OS(O)(=O)=O.CN(C)C1=CC2=[S+]C3=CC(N)=C(C)C=C3N=C2C=C1

InChI

InChIKey=GMJPSSGFWWXQJN-UHFFFAOYSA-M
InChI=1S/C15H16N3S.ClH.H2O4S/c1-9-6-13-15(8-11(9)16)19-14-7-10(18(2)3)4-5-12(14)17-13;;1-5(2,3)4/h4-8H,16H2,1-3H3;1H;(H2,1,2,3,4)/q+1;;/p-1

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C15H16N3S
Molecular Weight 270.373
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula HO4S
Molecular Weight 97.071
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Tolonium chloride (INN, also known as toluidine blue or TBO) is a phenothiazine that has been used as a hemostatic, a biological stain, and a dye for wool and silk. Tolonium chloride has also been used as a diagnostic aid for oral and gastric neoplasms and in the identification of the parathyroid gland in thyroid surgery. Toluidine blue has high affinity for acidic tissue components, thereby staining tissues rich in DNA and RNA. It has found wide applications both as vital staining in living tissues and as a special stain owing to its metachromatic property. Toluidine blue has been used in vivo to identify dysplasia and carcinoma of the oral cavity.

Originator

Perkin, W.H.
4
Curator's Comment: William Henry Perkin in 1856

Approval Year

1953
193
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1076
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Blutene

Approved Use

Treatment and prevention of excessive menstrual flow.
Diagnostic
Not Provided
511
Unknown

Approved Use

Unknown
Diagnostic
Phase III
665
Unknown

Approved Use

Unknown
Diagnostic
Phase III
665
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
2 mg/kg 1 times / day single, intravenous
Studied dose
Dose: 2 mg/kg, 1 times / day
Route: intravenous
Route: single
Dose: 2 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30349973/
unhealthy, 27 years
Health Status: unhealthy
Age Group: 27 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/30349973/
Other AEs: Edema...
Other AEs:
Edema
Sources:
https://pubmed.ncbi.nlm.nih.gov/30349973/
4 mg/kg 1 times / day single, intravenous
Studied dose
Dose: 4 mg/kg, 1 times / day
Route: intravenous
Route: single
Dose: 4 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/4176446/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://pubmed.ncbi.nlm.nih.gov/4176446/
Other AEs: Cardiac arrhythmia...
Other AEs:
Cardiac arrhythmia
Sources:
https://pubmed.ncbi.nlm.nih.gov/4176446/
AEs

AEs

AESignificanceDosePopulation
Edema
2 mg/kg 1 times / day single, intravenous
Studied dose
Dose: 2 mg/kg, 1 times / day
Route: intravenous
Route: single
Dose: 2 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30349973/
unhealthy, 27 years
Health Status: unhealthy
Age Group: 27 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/30349973/
Cardiac arrhythmia
4 mg/kg 1 times / day single, intravenous
Studied dose
Dose: 4 mg/kg, 1 times / day
Route: intravenous
Route: single
Dose: 4 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/4176446/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://pubmed.ncbi.nlm.nih.gov/4176446/
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:87648
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:87648
ZINC
ZINC000004217587
http://zinc15.docking.org/substances/ZINC000004217587
PubMed

PubMed

TitleDatePubMed
Toluidine blue: A review of its chemistry and clinical utility.
2012-05
ABC of oral health. Swellings and red, white, and pigmented lesions.
2000-07-22
Patents

Patents

JP2004524831A
13
JPH05331389A
3
JPS05653101A
3

Sample Use Guides

In Vivo Use Guide
Examination of the oral cavity after the local application of Toluidine Blue dye (tolonium chloride)
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:49:45 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:45 GMT 2025
Record UNII
H3CVU5X0VI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TOLONIUM CHLORIDE SULFATE
Common Name English
PHENOTHIAZIN-5-IUM, 3-AMINO-7-(DIMETHYLAMINO)-2-METHYL-, CHLORIDE, SULFATE (1:1)
Preferred Name English
PHENOTHIAZIN-5-IUM, 3-AMINO-7-(DIMETHYLAMINO)-2-METHYL-, CHLORIDE, SULFATE (1:1:1)
Systematic Name English
Code System Code Type Description
CAS
22239-28-7
Created by admin on Mon Mar 31 17:49:45 GMT 2025 , Edited by admin on Mon Mar 31 17:49:45 GMT 2025
PRIMARY
FDA UNII
H3CVU5X0VI
Created by admin on Mon Mar 31 17:49:45 GMT 2025 , Edited by admin on Mon Mar 31 17:49:45 GMT 2025
PRIMARY
EPA CompTox
DTXSID501016718
Created by admin on Mon Mar 31 17:49:45 GMT 2025 , Edited by admin on Mon Mar 31 17:49:45 GMT 2025
PRIMARY
Related Record Type Details
Structure of TOLONIUM
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