Dithizone

Dithizone
Skeletal formula of dithizone
Ball-and-stick model of the dithizone molecule
Names
IUPAC name
(1E)-3-anilino-1-phenylimino-thiourea
Other names
Diphenylthiocarbazone, 1,5-Diphenylthiocarbazone
Identifiers
CAS Number
  • 60-10-6 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 571406 checkY
ECHA InfoCard 100.000.413 Edit this at Wikidata
PubChem CID
  • 657262
UNII
  • NJZ2CJ4D6P checkY
CompTox Dashboard (EPA)
  • DTXSID0058770 Edit this at Wikidata
InChI
  • InChI=1S/C13H12N4S/c18-13(16-14-11-7-3-1-4-8-11)17-15-12-9-5-2-6-10-12/h1-10,14H,(H,16,18)/b17-15+ checkY
    Key: UOFGSWVZMUXXIY-BMRADRMJSA-N checkY
  • InChI=1/C13H12N4S/c18-13(16-14-11-7-3-1-4-8-11)17-15-12-9-5-2-6-10-12/h1-10,14H,(H,16,18)/b17-15+
    Key: UOFGSWVZMUXXIY-BMRADRMJBA
  • S=C(/N=N/c1ccccc1)NNc2ccccc2
Properties
Chemical formula
 C13H12N4S
Molar mass 256.33 g·mol−1
Hazards
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Dithizone is a sulfur-containing organic compound. It is a good ligand, and forms complexes with many toxic metals such as lead, thallium[1] and mercury.

Dithizone may be prepared by reacting phenylhydrazine with carbon disulfide, followed by reaction with potassium hydroxide.[2]

Dithizone is used to assess the purity of human pancreatic islet preparations used for transplantation into patients with type 1 diabetes. Dithizone binds zinc ions present in the islet's beta cells, and therefore stains the islets red. Exocrine tissue also present in the preparations does not bind dithizone, and is therefore not stained.

[3]

  • Dithizone
    Dithizone
  • Dithizone in Ethanol 96%
    Dithizone in Ethanol 96%

References

  1. ^ Bendl BJ (1969) Thallium poisoning: report of a case successfully treated with dithizone. Arch Dermatol 100:443–446 URL=https://jamanetwork.com/journals/jamadermatology/article-abstract/531202
  2. ^ John H. Billman and Elizabeth S. Cleland (1955). "Dithizone". Organic Syntheses; Collected Volumes, vol. 3, p. 360.
  3. ^ Ricordi, C; Gray, DW; Hering, BJ; Kaufman, DB; Warnock, GL; Kneteman, NM; Lake, SP; London, NJ; et al. (1990). "Islet isolation assessment in man and large animals" (PDF). Acta Diabetologica Latina. 27 (3): 185–95. doi:10.1007/BF02581331. PMID 2075782.