Thionine

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Chemical compound and histologic stain C12H10N3S

title: "Thionine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["staining-dyes", "phenothiazines"] description: "Chemical compound and histologic stain C12H10N3S" topic_path: "general/staining-dyes" source: "https://en.wikipedia.org/wiki/Thionine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound and histologic stain C12H10N3S ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424770911 | ImageFile = Thionine.svg | ImageSize = | ImageAlt = | PIN = 3,7-Diamino-5λ4-phenothiazin-5-ylium | OtherNames = |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 26754-93-8 | UNII_Ref = | UNII = 8CFV7T4334 | PubChem = 65043 | PubChem_Comment = (chloride salt) | ChemSpiderID_Ref = | ChemSpiderID = 10554883 | SMILES = C1=CC2=C(C=C1N)[S+]=C3C=C(C=CC3=N2)N | StdInChI_Ref = | StdInChI = 1S/C12H10N3S/c13-7-1-3-9-11(5-7)16-12-6-8(14)2-4-10(12)15-9/h1-6H,13-14H2/q+1 | StdInChIKey_Ref = | StdInChIKey = CBBMGBGDIPJEMI-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=12|H=10|N=3|S=1 | Formula_Charge = + | MolarMass = | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}

Thionine, also known as Lauth's violet, is the salt of a heterocyclic compound. It was firstly synthesised by Charles Lauth. A variety of salts are known including the chloride and acetate, called respectively thionine chloride and thionine acetate. The dye is structurally related to methylene blue, which also features a phenothiazine core. The dye's name is frequently misspelled with omission of the e, and is not to be confused with the plant protein thionin. The -ine ending indicates that the compound is an amine.

Dye properties and use

Thionine is a strongly staining metachromatic dye, which is widely used for biological staining. Thionine can also be used in place of Schiff reagent in quantitative Feulgen staining of DNA. It can also be used to mediate electron transfer in microbial fuel cells. Thionine is a pH-dependent redox indicator with E0 = 0.06 at pH 7.0. Its reduced form, leuco-thionine, is colorless.

When both the amines are dimethylated, the product tetramethyl thionine is the famous methylene blue, and the intermediates are Azure C (Monomethyl thionine), Azure A (when one of the amines is dimethylated and the other remains a primary amine), and Azure B (Trimethyl thionine). When methylene blue is "polychromed" by ripening (oxidized in solution or metabolized by fungal contamination, as originally noted in the thesis of Dr D L Romanowski in 1890s), it forms thionine and all the Azure intermediates.

References

  1. Gérard Taurand, "Phenothiazine and Derivatives" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2005.{{doi. 10.1002/14356007.a19_387
  2. Kiernan JA. (2001). "Classification and naming of dyes, stains and fluorochromes". Biotech Histochem.
  3. Webster's Third New International Dictionary. G & C Merriam Co. 1976, p.2377.
  4. "Stainsfile — Thionin".
  5. Eugenii Katz. (2003). "Handbook of Fuel Cells: Fundamentals, Technology, Applications, 4-Volume Set". Wiley.
  6. [http://www.dako.com/08066_12may10_webchapter19.pdf Dako Education Guide - Special Stains and H & E ” second edition Chapter 19: '''On Chemical Reactions and Staining Mechanisms''' by John A. Kiernan, Subsection '''What is Giemsa’s stain and how does it color blood cells, bacteria and chromosomes?''' p172] {{Webarchive. link. (2012-05-13)
  7. Wilson TM. (1907). "On the Chemistry and Staining Properties of Certain Derivatives of the Methylene Blue Group when Combined with Eosin". J Exp Med.
  8. Marshall, PN (1978) Romanowsky-type stains in haematology. Histochemical Journal 10: 1-29.

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staining-dyesphenothiazines