:Dithizone

{{Chembox

| verifiedrevid = 435967578

| ImageFile = Dithizon.svg

| ImageSize = 240

| ImageAlt = Skeletal formula of dithizone

| ImageFile1 = Dithizone 3D ball.png

| ImageSize1 = 240

| ImageAlt1 = Ball-and-stick model of the dithizone molecule

| IUPACName = (1E)-3-anilino-1-phenylimino-thiourea

| OtherNames = Diphenylthiocarbazone,

1,5-Diphenylthiocarbazone

|Section1={{Chembox Identifiers

| InChIKey = UOFGSWVZMUXXIY-BMRADRMJBA

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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+

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UOFGSWVZMUXXIY-BMRADRMJSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 60-10-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = NJZ2CJ4D6P

| PubChem = 657262

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 571406

| SMILES = S=C(/N=N/c1ccccc1)NNc2ccccc2

| 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+

}}

|Section2={{Chembox Properties

| C=13 | H=12 | N=4 | S=1

| Appearance =

| Density =

| MeltingPtC = 165 to 169

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| ExternalSDS = [http://msds.chem.ox.ac.uk/DI/dithizone.html External MSDS]

| FlashPt =

| AutoignitionPt =

}}

}}

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

Dithizone may be prepared by reacting phenylhydrazine with carbon disulfide, followed by reaction with potassium hydroxide.{{OrgSynth | title = Dithizone | collvol = 3 | collvolpages = 360 | year = 1955 | prep = cv3p0360 | author = John H. Billman and Elizabeth S. Cleland}}

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.

{{cite journal | last1 = Ricordi | first1 = C | last2 = Gray | first2 = DW | last3 = Hering | first3 = BJ | last4 = Kaufman | first4 = DB | last5 = Warnock | first5 = GL | last6 = Kneteman | first6 = NM | last7 = Lake | first7 = SP | last8 = London | first8 = NJ | last9 = Socci | first9 = C | last10 = Alejandro | first10 = Rodolfo | last11 = Zeng | first11 = Yijun | last12 = Scharp | first12 = David W. | last13 = Viviani | first13 = Giorgio | last14 = Falqui | first14 = Luca | last15 = Tzakis | first15 = Andreas | last16 = Bretzel | first16 = Reinhard G. | last17 = Federlin | first17 = Konrad | last18 = Pozza | first18 = Guido | last19 = James | first19 = Roger F. L. | last20 = Rajotte | first20 = Ray V. | last21 = Carlo | first21 = Valerio Di | last22 = Morris | first22 = Peter J. | last23 = Sutherland | first23 = David E. R. | last24 = Starzl | first24 = Thomas E. | last25 = Mintz | first25 = Daniel H. | last26 = Lacy | first26 = Paul E. | title = Islet isolation assessment in man and large animals | journal = Acta Diabetologica Latina | volume = 27 | issue = 3 | pages = 185–95 | year = 1990 | pmid = 2075782 | doi = 10.1007/BF02581331 | display-authors = 8 | url = http://d-scholarship.pitt.edu/4513/1/31735062116805.pdf }}

File:Dithizone by Danny S. - 001.JPG|Dithizone

File:Dithizone by Danny S. - 002.JPG|Dithizone in Ethanol 96%