Dithizone

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Dithizone
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Names
IUPAC name
(1E)-3-anilino-1-phenylimino-thiourea
Other names
Diphenylthiocarbazone, 1,5-Diphenylthiocarbazone
Identifiers
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3D model (JSmol)
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  • 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
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).

Template:Chembox Footer/trackingTemplate:Short description

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. ^ Page Module:Citation/CS1/styles.css has no content.John H. Billman and Elizabeth S. Cleland (1955). "Dithizone". Organic Syntheses; Page Module:Citation/CS1/styles.css has no content.Collected Volumes, vol. 3, p. 360.
  3. ^ Page Module:Citation/CS1/styles.css has no content.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.
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