Dithizone

Last updated
Dithizone
Dithizon.svg
Dithizone 3D ball.png
Names
IUPAC name
(1E)-3-anilino-1-phenylimino-thiourea
Other names
Diphenylthiocarbazone, 1,5-Diphenylthiocarbazone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.413 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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+ Yes check.svgY
    Key: UOFGSWVZMUXXIY-BMRADRMJSA-N Yes check.svgY
  • 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
C13H12N4S
Molar mass 256.33 g·mol−1
Melting point 165 to 169 °C (329 to 336 °F; 438 to 442 K)
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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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]

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.