Thioacetamide

Thioacetamide
Names
	IUPAC name Thioacetamide
	Preferred IUPAC name Ethanethioamide
	Other names acetothioamide, TAA, thioacetimidic acid, TA, TAM
Identifiers
CAS Number	62-55-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	506006
ChEBI	CHEBI:32497 ;
ChEMBL	ChEMBL38737 ;
ChemSpider	2006126 ;
ECHA InfoCard	100.000.493
EC Number	200-541-4;
KEGG	C19302 ;
PubChem CID	2723949;
RTECS number	AC8925000;
UNII	075T165X8M ;
UN number	3077
CompTox Dashboard (EPA)	DTXSID9021340 ;
	InChI InChI=1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4) Key: YUKQRDCYNOVPGJ-UHFFFAOYSA-N ; InChI=1/C2H5NS/c1-2(3)4/h1H3,(H2,3,4) Key: YUKQRDCYNOVPGJ-UHFFFAOYAD;
	SMILES S=C(N)C;
Properties
Chemical formula	C2H5NS
Molar mass	75.13 g/mol
Appearance	colourless crystals
Odor	slight mercaptan
Density	1.319 g/cm3
Melting point	115 °C (239 °F; 388 K)
Boiling point	decomposes
Solubility in water	good
Magnetic susceptibility (χ)	-42.45·10−6 cm3/mol
Structure
Crystal structure	monoclinic
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Foul stench, carcinogenic
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H319, H350, H412
Precautionary statements	P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P321, P330, P332+P313, P337+P313, P362, P405, P501
Safety data sheet (SDS)	MSDS
Related compounds
Related compounds	acetamide, dithioacetic acid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Thioacetamide is an organosulfur compound with the formula C₂ H₅ N S. 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.^[3]

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:^[4]

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.^[2]

Safety

Thioacetamide is carcinogen class 2B.

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).^[5] This is evidenced by enzymatic changes, which include elevation in the levels of serum alanine transaminase, aspartate transaminase and aspartic acid.^[6]

References

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 856. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ ^a ^b Trevor W. Hambley; David E. Hibbs; Peter Turner; Siân. T. Howard; Michael B. Hursthouse (2002). "Insights into Bonding and Hydrogen Bond Directionality in Thioacetamide from the Experimental Charge Distribution". J. Chem. Soc., Perkin Trans. (2): 235–239. doi:10.1039/B109353C.
^ Dwivedi DK, Jena GB (2018). "Glibenclamide protects against thioacetamide-induced hepatic damage in Wistar rat: investigation on NLRP3, MMP-2, and stellate cell activation". Naunyn-Schmiedeberg's Archives of Pharmacology. 391 (11): 1257–1274. doi:10.1007/s00210-018-1540-2. PMID 30066023. S2CID 51890984.
^ Schwarz, G. (1945). "2,4-Dimethylthiazole". Organic Syntheses. 25: 35; Collected Volumes, vol. 3, p. 332.
^ "HSDB: THIOACETAMIDE CASRN: 62-55-5". Hazardous Substances Data Bank.
^ Ali, S.; Ansari, K. A.; Jafry, M. A.; Kabeer, H.; Diwakar, G. (2000). "Nardostachys jatamansi protects against liver damage induced by thioacetamide in rats". Journal of Ethnopharmacology. 71 (3): 359–363. doi:10.1016/S0378-8741(99)00153-1. PMID 10940571.

"Thioacetamide (Sulfo amine)". Chemical Land 21. Retrieved February 14, 2006.

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 856. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[Hurst-2] Trevor W. Hambley; David E. Hibbs; Peter Turner; Siân. T. Howard; Michael B. Hursthouse (2002). "Insights into Bonding and Hydrogen Bond Directionality in Thioacetamide from the Experimental Charge Distribution". J. Chem. Soc., Perkin Trans. (2): 235–239. doi:10.1039/B109353C.

[3] Dwivedi DK, Jena GB (2018). "Glibenclamide protects against thioacetamide-induced hepatic damage in Wistar rat: investigation on NLRP3, MMP-2, and stellate cell activation". Naunyn-Schmiedeberg's Archives of Pharmacology. 391 (11): 1257–1274. doi:10.1007/s00210-018-1540-2. PMID 30066023. S2CID 51890984.

[4] Schwarz, G. (1945). "2,4-Dimethylthiazole". Organic Syntheses. 25: 35; Collected Volumes, vol. 3, p. 332.

[5] "HSDB: THIOACETAMIDE CASRN: 62-55-5". Hazardous Substances Data Bank.

[6] Ali, S.; Ansari, K. A.; Jafry, M. A.; Kabeer, H.; Diwakar, G. (2000). "Nardostachys jatamansi protects against liver damage induced by thioacetamide in rats". Journal of Ethnopharmacology. 71 (3): 359–363. doi:10.1016/S0378-8741(99)00153-1. PMID 10940571.

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