Thioacetamide: Difference between revisions

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	{{chembox		{{chembox
	\| Verifiedfields = changed		\| Verifiedfields = changed
			\| Watchedfields = changed
	\| verifiedrevid = ~~418298272~~		\| verifiedrevid = 470606721
	\| Name = Thioacetamide		\| Name = Thioacetamide
	\| ImageFile = TA.png
		⚫	\| ImageFile = Ethanethioamide 200.svg
	\| ImageSize = 140px		\| ImageSize = 140px
	\| ~~ImageName~~ = Structural formula		\| ImageAlt = Structural formula of thioacetamide
	\| ImageFile1 = Thioacetamide-3D~~-balls~~.png		\| ImageFile1 = Thioacetamide 3D ball.png
	\| ImageSize1 = 170px		\| ImageSize1 = 170px
	\| ImageName1 = Ball-and-stick model
			\| ImageAlt1 = Ball-and-stick model of the thioacetamide molecule
⚫	\| ~~PIN~~ = Ethanethioamide
	\| IUPACName = Thioacetamide		\| IUPACName = Thioacetamide
			\| 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>
	\| OtherNames = acetothioamide, TAA, thioacetimidic acid, TA		\| OtherNames = acetothioamide, TAA, thioacetimidic acid, TA, TAM
	\| Section1 = {{Chembox Identifiers		\| Section1 = {{Chembox Identifiers
			\| CASNo = 62-55-5
⚫	\| UNII_Ref = {{fdacite\|~~changed~~\|FDA}}
		⚫	\| CASNo_Ref = {{cascite\|correct\|CAS}}
⚫	\| UNII = 075T165X8M
			\| Beilstein = 506006
	\| ChEBI_Ref = {{ebicite\|~~changed~~\|EBI}}		\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI = 32497		\| ChEBI = 32497
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| SMILES = S=C(N)C
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 2006126		\| ChemSpiderID = 2006126
			\| EC_number = 200-541-4
	\| PubChem = 2723949		\| PubChem = 2723949
⚫	\| InChI = 1/C2H5NS/c1-2(3)4/h1H3,(H2,3,4)
⚫	\| InChIKey = YUKQRDCYNOVPGJ-UHFFFAOYAD
	\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}		\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 38737		\| 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_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4)		\| StdInChI = 1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4)
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = YUKQRDCYNOVPGJ-UHFFFAOYSA-N		\| StdInChIKey = YUKQRDCYNOVPGJ-UHFFFAOYSA-N
	\| ~~CASNo~~ = ~~62-55-5~~		\| SMILES = S=C(N)C
⚫	\| CASNo_Ref = {{cascite\|correct\|CAS}}
⚫	\| RTECS = AC8925000
⚫	\| KEGG_Ref = {{keggcite\|~~changed~~\|kegg}}
⚫	\| KEGG = C19302
	}}		}}
	\| Section2 = {{Chembox Properties		\| Section2 = {{Chembox Properties
	\| Formula = C<sub>2</sub>H<sub>5</sub>NS		\| Formula = C<sub>2</sub>H<sub>5</sub>NS
	\| MolarMass = 75.13 g/mol		\| MolarMass = 75.13 g/mol
	\| Appearance = colourless crystals, slight ] ~~odor~~		\| Appearance = colourless crystals
			\| Odor = slight ]
	\| Density = 1.~~269~~ g/cm³<~~!--from~~ ~~X-ray structure --~~>		\| Density = 1.319 g/cm<sup>3</sup><ref name=Hurst/>
	\| Solubility = good~~, with hydrolysis~~		\| Solubility = good
	\| ~~MeltingPt~~ = 115 °C		\| MeltingPtC = 115
	\| BoilingPt = ~~decomp.~~		\| BoilingPt = decomposes
			\| MagSus = -42.45·10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
	\| Section3 = {{Chembox Structure		\| Section3 = {{Chembox Structure
	\| CrystalStruct = ]		\| CrystalStruct = ]
	\| Dipole =		\| Dipole =
	}}		}}
			\| Section4 =
			\| Section5 =
			\| Section6 =
	\| Section7 = {{Chembox Hazards		\| Section7 = {{Chembox Hazards
			\| ExternalSDS =
	\| ExternalMSDS =
	\| MainHazards = stench		\| MainHazards = Foul stench, ]
	\| FlashPt = ~~?°C~~		\| FlashPt =
			\| GHSPictograms = {{GHS07}}{{GHS08}}
	\| RPhrases = R22 R36 R37 R45
			\| GHSSignalWord = Danger
	\| SPhrases = S45 S53
			\| 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		\| Section8 = {{Chembox Related
	\| ~~OtherCpds~~ = ], dithioacetic acid		\| OtherCompounds = ], ]
	}}		}}
	}}		}}

	'''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 ].		'''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 ].

			==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==		==Coordination chemistry==
	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:		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:
	: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)		: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)
	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>).		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>).

	==Preparation==		==Preparation==
	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>		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>
	: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>		: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>

	==Structure==		==Structure==
	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>		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>

	==Safety==		==Safety==
	Thioacetamide is ] class 2B.		Thioacetamide is ] class 2B.

	It is known to produce marked ]ity in exposed animals. This is evidenced by enzymatic changes, which include elevation in the levels of serum ], ] and ]. <ref>http://www.sciencedirect.com/science/article/pii/S0378874199001531</ref>
			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>

	==References==		==References==
	{{Reflist}}		{{Reflist}}
	* {{cite web \| title="Thioacetamide (Sulfo amine)" \| work=Chemical Land 21\| url=http://www.chemicalland21.com/specialtychem/finechem/THIOACETAMIDE.htm\| ~~accessdate~~=February 14, 2006}}		* {{cite web \| title = Thioacetamide (Sulfo amine) \| work = Chemical Land 21 \| url = http://www.chemicalland21.com/specialtychem/finechem/THIOACETAMIDE.htm \| access-date = February 14, 2006 }}

			{{Authority control}}

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Latest revision as of 12:48, 1 March 2024

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/cm
Melting point	115 °C (239 °F; 388 K)
Boiling point	decomposes
Solubility in water	good
Magnetic susceptibility (χ)	-42.45·10 cm/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 , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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.

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:

M + CH₃C(S)NH₂ + H₂O → MS + CH₃C(O)NH₂ + 2 H (M = Ni, Pb, Cd, Hg)

Related precipitations occur for sources of soft trivalent cations (As, Sb, Bi) and monovalent cations (Ag, Cu).

Preparation

Thioacetamide is prepared by treating acetamide with phosphorus pentasulfide as shown in the following idealized reaction:

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.

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

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.
^ 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.

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