| Revision as of 14:05, 11 March 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 402685045 |
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| Watchedfields = changed |
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| Name = Thioacetamide |
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| verifiedrevid = 470606721 |
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| ImageFile = TA.png |
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| Name = Thioacetamide |
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| ImageSize = 140px |
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| ImageFile = Ethanethioamide 200.svg |
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| ImageName = Structural formula |
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| ImageSize = 140px |
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| ImageFile1 = Thioacetamide-3D-balls.png |
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| ImageAlt = Structural formula of thioacetamide |
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| ImageSize1 = 170px |
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| ImageFile1 = Thioacetamide 3D ball.png |
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| ImageName1 = Ball-and-stick model |
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| ImageSize1 = 170px |
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| PIN = Ethanethioamide |
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| ImageAlt1 = Ball-and-stick model of the thioacetamide molecule |
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| IUPACName = Thioacetamide |
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| IUPACName = Thioacetamide |
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| OtherNames = acetothioamide, TAA, thioacetimidic acid, TA |
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| PIN = Ethanethioamide<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |page=856 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| OtherNames = acetothioamide, TAA, thioacetimidic acid, TA, TAM |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| SMILES = S=C(N)C |
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| CASNo = 62-55-5 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Beilstein = 506006 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 32497 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2006126 |
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| ChemSpiderID = 2006126 |
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| EC_number = 200-541-4 |
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| PubChem = 2723949 |
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| PubChem = 2723949 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 38737 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C19302 |
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| RTECS = AC8925000 |
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| UNNumber = 3077 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 075T165X8M |
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| InChI = 1/C2H5NS/c1-2(3)4/h1H3,(H2,3,4) |
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| InChI = 1/C2H5NS/c1-2(3)4/h1H3,(H2,3,4) |
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| InChIKey = YUKQRDCYNOVPGJ-UHFFFAOYAD |
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| InChIKey = YUKQRDCYNOVPGJ-UHFFFAOYAD |
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| ChEMBL = 38737 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4) |
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| StdInChI = 1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = YUKQRDCYNOVPGJ-UHFFFAOYSA-N |
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| StdInChIKey = YUKQRDCYNOVPGJ-UHFFFAOYSA-N |
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| CASNo = 62-55-5 |
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| SMILES = S=C(N)C |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| RTECS = AC8925000 |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>2</sub>H<sub>5</sub>NS |
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| Formula = C<sub>2</sub>H<sub>5</sub>NS |
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| MolarMass = 75.13 g/mol |
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| MolarMass = 75.13 g/mol |
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| Appearance = colourless crystals, slight ] odor |
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| Appearance = colourless crystals |
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| Odor = slight ] |
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| Density = 1.269 g/cm³<!--from X-ray structure --> |
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| Density = 1.319 g/cm<sup>3</sup><ref name=Hurst/> |
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| Solubility = good, with hydrolysis |
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| Solubility = good |
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| MeltingPt = 115 °C |
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| MeltingPtC = 115 |
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| BoilingPt = decomp. |
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| BoilingPt = decomposes |
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| MagSus = -42.45·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Section3 = {{Chembox Structure |
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| Section3 = {{Chembox Structure |
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| CrystalStruct = ] |
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| CrystalStruct = ] |
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| Dipole = |
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| Dipole = |
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| Section4 = |
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| Section5 = |
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| Section6 = |
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| Section7 = {{Chembox Hazards |
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| Section7 = {{Chembox Hazards |
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| ExternalSDS = |
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| ExternalMSDS = |
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| MainHazards = stench |
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| MainHazards = Foul stench, ] |
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| FlashPt = ?°C |
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| FlashPt = |
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| GHSPictograms = {{GHS07}}{{GHS08}} |
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| RPhrases = R22 R36 R37 R45 |
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| GHSSignalWord = Danger |
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| SPhrases = S45 S53 |
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| HPhrases = {{H-phrases|302|315|319|350|412}} |
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| 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}} |
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| Section8 = {{Chembox Related |
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| Section8 = {{Chembox Related |
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| OtherCpds = ], dithioacetic acid |
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| OtherCompounds = ], ] |
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'''Thioacetamide''' is an ] with the ] ]]]]. This white crystalline solid is soluble in water and serves as a source of ] ions in the synthesis of organic and inorganic compounds. It is a prototypical ]. |
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'''Thioacetamide''' is an ] with the ] ]]]]. This white crystalline solid is soluble in water and serves as a source of ] ions in the synthesis of organic and inorganic compounds. It is a prototypical ]. |
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==Research== |
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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> |
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==Coordination chemistry== |
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==Coordination chemistry== |
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Thioacetamide was widely used in classical ] 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: |
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Thioacetamide is widely used in classical ] 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: |
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:M<sup>2+</sup> + CH<sub>3</sub>C(S)NH<sub>2</sub> + H<sub>2</sub>O → MS + CH<sub>3</sub>C(O)NH<sub>2</sub> + 2 H<sup>+</sup> (M = Ni, Pb, Cd, Hg) |
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:M<sup>2+</sup> + CH<sub>3</sub>C(S)NH<sub>2</sub> + H<sub>2</sub>O → MS + CH<sub>3</sub>C(O)NH<sub>2</sub> + 2 H<sup>+</sup> (M = Ni, Pb, Cd, Hg) |
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Related precipitations occur for sources of ] trivalent cations (As<sup>3+</sup>, Sb<sup>3+</sup>, Bi<sup>3+</sup>) and monovalent cations (Ag<sup>+</sup>, Cu<sup>+</sup>). |
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Related precipitations occur for sources of ] trivalent cations (As<sup>3+</sup>, Sb<sup>3+</sup>, Bi<sup>3+</sup>) and monovalent cations (Ag<sup>+</sup>, Cu<sup>+</sup>). |
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==Preparation== |
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==Preparation== |
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Thioacetamide is prepared by treating acetamide with ] as shown in the following idealized reaction:<ref>{{OrgSynth | author = George Schwarz | title = 2,4-Dimethylthiazole | collvol = 3 | collvolpages = 332 | year = 1955 | prep = cv3p0332}}</ref> |
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Thioacetamide is prepared by treating acetamide with ] 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> |
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:CH<sub>3</sub>C(O)NH<sub>2</sub> + 1/4 P<sub>4</sub>S<sub>10</sub> → CH<sub>3</sub>C(S)NH<sub>2</sub> + 1/4 P<sub>4</sub>S<sub>6</sub>O<sub>4</sub> |
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:CH<sub>3</sub>C(O)NH<sub>2</sub> + 1/4 P<sub>4</sub>S<sub>10</sub> → CH<sub>3</sub>C(S)NH<sub>2</sub> + 1/4 P<sub>4</sub>S<sub>6</sub>O<sub>4</sub> |
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==Structure== |
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==Structure== |
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The C<sub>2</sub>NH<sub>2</sub>S portion of the molecule is planar; the C-S and C-N distances are 1.713 and 1.324 Å, both indicating multiple bonding.<ref>Mary R. Truter "An accurate determination of the crystal structure of thioacetamide" Journal of the Chemical Society, 1960, pp. 997-1007. DOI: 10.1039/JR9600000997</ref> |
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The C<sub>2</sub>NH<sub>2</sub>S 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> |
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==Safety== |
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==Safety== |
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Thioacetamide is ] class 2B. |
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Thioacetamide is ] class 2B. |
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It is known to produce marked hepatotoxicity in exposed animals. Toxicity values are 301 mg/kg in rats (LD50, oral administration), 300 mg/kg in mice (LD50, intraperitoneal administration).<ref>{{ cite web | url = http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+@rel+62-55-5 | 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 ], ] and ].<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> |
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==References== |
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==References== |
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{{Reflist}} |
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{{Reflist}} |
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* {{cite web | title="Thioacetamide (Sulfo amine)" | work=Chemical Land 21| url=http://www.chemicalland21.com/specialtychem/finechem/THIOACETAMIDE.htm| accessdate=February 14, 2006}} |
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* {{cite web | title = Thioacetamide (Sulfo amine) | work = Chemical Land 21 | url = http://www.chemicalland21.com/specialtychem/finechem/THIOACETAMIDE.htm | access-date = February 14, 2006 }} |
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