Thioflavin T
Basic information
- CAS
2390-54-7- Standard SMILES
Cc1ccc2c(c1)sc(-c1ccc(N(C)C)cc1)[n+]2C.[Cl-]- InChIKey
JADVWWSKYZXRGX-UHFFFAOYSA-M- Molecular formula
- C17H19N2S.Cl
- Average molar mass
- 318.9 g/mol
- Monoisotopic mass
- 318.0957475
Overview
Thioflavine T is an organic chloride salt having 2-[4-(dimethylamino)phenyl]-3,6-dimethyl-1,3-benzothiazol-3-ium as the counterion. It is widely used to visualise and quantify the presence of amyloids, both in vitro and in vivo. It has a role as a geroprotector, a fluorochrome and a histological dye. It contains a thioflavin T cation.
Names & identifiers
- Preferred name
- Thioflavin T
- IUPAC
- 4-(3,6-dimethyl-1,3-benzothiazol-3-ium-2-yl)-N,N-dimethylaniline chloride
- English name
- Thioflavin T
- Molecular formula
- C17H19ClN2S
- Molecular weight
- 318.86
Names & synonyms
Thioflavin T2390-54-7Thioflavine TBasic yellow 1Acronol Yellow TCC.I. Basic Yellow 1C.I. 49005CAX9SG0II0Benzothiazolium, 2-[4-(dimethylamino)phenyl]-3,6-dimethyl-, chloride3,6-Dimethyl-2-dimethylaminophenylbenzothiazolium chlorideNSC-11235Benzothiazolium, 2-(p-(dimethylamino)phenyl)-3,6-dimethyl-, chloride
Show more names
CI 490052-[4-(dimethylamino)phenyl]-3,6-dimethyl-benzothiazoliuchlorideThiofLavin TCI NO 49005hioflavineTSetoflavin T
CHEBI:76023DTXSID10883841Benzothiazolium, 2-(4-(dimethylamino)phenyl)-3,6-dimethyl-, chlorideBenzothiazolium, 2-(4-(dimethylamino)phenyl)-3,6-dimethyl-, chloride (1:1)2-(p-(dimethylamino)phenyl)-3,6-dimethylbenzothiazolium chlorideBenzothiazolium, 2-[4-(dimethylamino)phenyl]-3,6-dimethyl-, chloride (1:1)ThT (dye)RefChem:189525
Database identifiers
Properties
Computed structural properties
- Topological polar surface area
- 35.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 325
Physicochemical properties
- Melting point
- 211 · 211-212 °C (decomp)
- Density
- 1.301 g/cm3 · 1.301g/cm3 at 20℃
- vapor pressure
- 0 Pa · 0Pa at 25℃
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 1 mg/mL · methanol: soluble1mg/mL
- Colour Index
- 49005 · 49005
- form
- Powder
- color
- Yellow to ochre-yellow
- Water Solubility
- 5 mg/mL · water: 5mg/mL
- BRN
- 3922452 · 3922452
- InChI
- InChI=1S/C17H19N2S.ClH/c1-12-5-10-15-16(11-12)20-17(19(15)4)13-6-8-14(9-7-13)18(2)3;/h5-11H,1-4H3;1H/q+1;/p-1
- InChIKey
- JADVWWSKYZXRGX-UHFFFAOYSA-M
- SMILES
- C1(=[N+](C)C2C=CC(C)=CC=2S1)C1C=CC(N(C)C)=CC=1.[Cl-]
- LogP
- 3.02 at · 3.02 at 25℃ and pH7.98
- CAS DataBase Reference
- 2390 · 2390-54-7(CAS DataBase Reference)
- FDA UNII
- 9 SG0II0 · CAX9SG0II0
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 21.4% (3 of 14) of reports.
Danger
H301 (78.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P273, P280, P301+P316, P302+P352, P305+P354+P338, P317, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 14 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzothiazolium, 2-[4-(dimethylamino)phenyl]-3,6-dimethyl-,chloride
REACH registered substance: 2-[4-(dimethylamino)phenyl]-3,6-dimethylbenzothiazolium chloride (EC: 219-228-9)
Thioflavine T: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 3 (78.6%)
Safety data
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- 2811
- hs_code
- 32041300
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- hazard_class
- 6.1(b)
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.
Uses & manufacturing
General Manufacturing InformationBenzothiazolium, 2-[4-(dimethylamino)phenyl]-3,6-dimethyl-, chloride (1:1): ACTIVE
Applications
HistoryIn 1959, Vassar and Culling first employed Thioflavin T (ThT) for the fluorescence imaging of amyloid plaques, revealing its potential for histological staining. In 1993, LeVine standardized the method for quantifying fibril formation using ThT, providing a simple fluorescence-based approach for studying protein folding and aggregation kinetics[1].
UsesThioflavin T (ThT) is usually used for detecting several types systemic amyloid proteins, including Alzheimer's disease, prion diseases. Currently, the ThT fluorescence regulation strategies mainly include amyloid fibrils binding, DNA modification, metal ion coordination, micelle regulation, etc. ThT is also gradually used in the detection of heavy metal ions, biotoxins, and residues of pesticide and veterinary drug, due to its cheap price, good organism compatibility, light stability, and sensitivity to the environment[2].
UsesTextile dyeing, fluorescent sign paints, in combination with green or blue pigments to produce brilliant greens, phosphotungstic pigments.
UsesA dye used to visualize beta-amyloid plaques, like those associated with Alzheimer's Disease
General DescriptionThioflavin T is a benzothiazole dye that increases in fluorescence upon binding to amyloid. Thioflavin T has been used in histology and for protein characterization.
Related reactions
0 records
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Compound notes
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