Thioacetamide

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470606721 | Name = Thioacetamide | ImageFile = Ethanethioamide 200.svg | ImageSize = 140px | ImageAlt = Structural formula of thioacetamide | ImageFile1 = Thioacetamide 3D ball.png | ImageSize1 = 170px | ImageAlt1 = Ball-and-stick model of the thioacetamide molecule | IUPACName = Thioacetamide | PIN = Ethanethioamide<ref>{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |page=856 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> | OtherNames = acetothioamide, TAA, thioacetimidic acid, TA, TAM | Section1 = {{Chembox Identifiers | CASNo = 62-55-5 | CASNo_Ref = {{cascite|correct|CAS}} | Beilstein = 506006 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 32497 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 2006126 | EC_number = 200-541-4 | PubChem = 2723949 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 38737 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C19302 | RTECS = AC8925000 | UNNumber = 3077 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 075T165X8M | InChI = 1/C2H5NS/c1-2(3)4/h1H3,(H2,3,4) | InChIKey = YUKQRDCYNOVPGJ-UHFFFAOYAD | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YUKQRDCYNOVPGJ-UHFFFAOYSA-N | SMILES = S=C(N)C }} | Section2 = {{Chembox Properties | Formula = C₂H₅NS | MolarMass = 75.13 g/mol | Appearance = colourless crystals | Odor = slight mercaptan | Density = 1.319 g/cm³<ref name=Hurst/> | Solubility = good | MeltingPtC = 115 | BoilingPt = decomposes | MagSus = −42.45·10⁻⁶ cm³/mol }} | Section3 = {{Chembox Structure | CrystalStruct = monoclinic | Dipole = }} | Section4 = | Section5 = | Section6 = | Section7 = {{Chembox Hazards | ExternalSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=163678&brand=SIAL&PageToGoToURL=http%3A//www.sigmaaldrich.com/catalog/search%3Finterface%3DAll%26term%3Dthioacetamide%26lang%3Den%26region%3DUS%26focus%3Dproduct%26N%3D0%2B220003048%2B219853269%2B219853286%26mode%3Dmatch%2520partialmax MSDS] | MainHazards = Foul stench, carcinogenic | FlashPt = | GHSPictograms = {{GHS07}}{{GHS08}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|302|315|319|350|412}} | PPhrases = {{P-phrases|201|202|264|270|273|280|281|301+312|302+352|305+351+338|308+313|321|330|332+313|337+313|362|405|501}} }} | Section8 = {{Chembox Related | OtherCompounds = acetamide, dithioacetic acid }} }}

'''Thioacetamide''' is an organosulfur compound with the formula C₂H₅NS. This white crystalline solid is soluble in water and serves as a source of sulfide ions in the synthesis of organic and inorganic compounds. It is a prototypical thioamide.

==Research== Thioacetamide is known to induce acute or chronic liver disease (fibrosis and cirrhosis) in the experimental animal model. Its administration in rat induces hepatic encephalopathy, metabolic acidosis, increased levels of transaminases, abnormal coagulation, and centrilobular necrosis, which are the main features of the clinical chronic liver disease so thioacetamide can precisely replicate the initiation and progression of human liver disease in an experimental animal model.<ref>{{cite journal |last1=Dwivedi DK |first1=Jena GB |title=Glibenclamide protects against thioacetamide-induced hepatic damage in Wistar rat: investigation on NLRP3, MMP-2, and stellate cell activation |journal=Naunyn-Schmiedeberg's Archives of Pharmacology |volume=391 |issue=11 |pages=1257–1274 |doi=10.1007/s00210-018-1540-2 |year=2018 |pmid=30066023|s2cid=51890984 }}</ref>

==Coordination chemistry== Thioacetamide is widely used in classical qualitative inorganic analysis as an in situ source for sulfide ions. Thus, treatment of aqueous solutions of many metal cations to a solution of thioacetamide affords the corresponding metal sulfide: :M²⁺ + CH₃C(S)NH₂ + H₂O → MS + CH₃C(O)NH₂ + 2 H⁺ (M = Ni, Pb, Cd, Hg) Related precipitations occur for sources of soft trivalent cations (As³⁺, Sb³⁺, Bi³⁺) and monovalent cations (Ag⁺, Cu⁺).

==Preparation== Thioacetamide is prepared by treating acetamide with phosphorus pentasulfide as shown in the following idealized reaction:<ref>{{ OrgSynth | author = Schwarz, G. | title = 2,4-Dimethylthiazole | volume = 25 | pages = 35 | collvol = 3 | collvolpages = 332 | year = 1945 | prep = cv3p0332 }}</ref> :CH₃C(O)NH₂ + 1/4 P₄S₁₀ → CH₃C(S)NH₂ + 1/4 P₄S₆O₄

==Structure== The C₂NH₂S portion of the molecule is planar; the C-S, C-N, and C-C distances are 1.68, 1.31, and 1.50 Å, respectively. The short C-S and C-N distances indicate multiple bonding.<ref name=Hurst>{{ cite journal |author=Trevor W. Hambley |author2=David E. Hibbs |author3=Peter Turner |author4=Siân. T. Howard |author5=Michael B. Hursthouse | title = Insights into Bonding and Hydrogen Bond Directionality in Thioacetamide from the Experimental Charge Distribution | journal = J. Chem. Soc., Perkin Trans. | year = 2002| pages = 235–239| doi = 10.1039/B109353C | issue=2}}</ref>

==Safety== Thioacetamide is a potential human carcinogen, class 2B.

It is known to produce marked hepatotoxicity in exposed animals. Toxicity values are 301&nbsp;mg/kg in rats (LD50, oral administration), 300&nbsp;mg/kg in mice (LD50, intraperitoneal administration).<ref>{{ cite web | url = https://www.nlm.nih.gov/toxnet/index.html | title = HSDB: THIOACETAMIDE CASRN: 62-55-5 | work = Hazardous Substances Data Bank }}</ref> This is evidenced by enzymatic changes, which include elevation in the levels of serum alanine transaminase, aspartate transaminase and aspartic acid.<ref>{{ cite journal |author1=Ali, S. |author2=Ansari, K. A. |author3=Jafry, M. A. |author4=Kabeer, H. |author5=Diwakar, G. | title = ''Nardostachys jatamansi'' protects against liver damage induced by thioacetamide in rats | journal = Journal of Ethnopharmacology | year = 2000 | volume = 71 | issue = 3 | pages = 359–363 | doi = 10.1016/S0378-8741(99)00153-1 |pmid=10940571 }}</ref>

==References== {{Reflist}}

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Category:IARC Group 2B carcinogens Category:Thioamides Category:Hepatotoxins