チオアセトアミド

Thioacetamide

HCID 2723949CAS 62-55-5

基本情報

標準SMILES
CC(N)=S
InChIKey
YUKQRDCYNOVPGJ-UHFFFAOYSA-N
分子式
C2H5NS
平均分子量
75.14 g/mol
単同位体質量
75.01427016

概要

Thioacetamide can cause cancer according to an independent committee of scientific and health experts.

名称と識別子

優先名称
Thioacetamide
IUPAC
ethanethioamide
現地名
チオアセトアミド
英語名
Thioacetamide
分子式
C2H5NS
分子量
75.13

名称と別名

THIOACETAMIDEEthanethioamide62-55-5AcetothioamideThiacetamideAcetamide, thio-Thioacetimidic acidAcetimidic acid, thio-USAF CB-21USAF EK-1719ThiacetamidAcetic acid, thiono-, amide
名称をさらに表示
チオアセトアミドエタンチオアミドアセトイミドチオ酸1-イミノエタンチオールチオアセトアミド STANDARDチオアセトアミド, ACSチオアセトアミド Standard, 1000 µg/mL in Acetonitrileチオアセトアミド, ACS, 99% minチオアセタミドTAACH3CSNH2THIOACETAMIDE ACS REAGENTusafcb-21usafek-1719hioacetamideThioactamide
DTXSID9021340NSC-2120075T165X8MDTXCID901340CHEBI:32497NSC2120ThioacetamidSulfo-amine

データベース識別子

CAS
62-55-5、65680-21-9
PubChem CID
2723949
DTXSID
DTXSID9021340
ChEMBL
CHEMBL38737
ChEBI
CHEBI:32497
UNII
075T165X8M
EC Number
200-541-4
Nikkaji
J2.350G

物性

構造計算による物性

XLogP
-0.3
極性表面積
58.1 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
0
重原子数
4

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Sulfur Compounds

Carcinogens

SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP · 2 件

log Kow = -0.26

-0.46/-0.36

OdorSlight odor of mercaptans
Color/Form · 4 件

Crystals from benzene

Colorless leaflets

Yellow tablets

CRYSTALS FROM ALC, PLATES FROM ETHER

Solubility · 6 件

5 to 10 mg/mL at 68 °F (NTP, 1992)

In ethanol 26.4 g/100 g; sparingly sol in ether

Miscible in benzene

MISCIBLE IN PETROLEUM ETHER

In water, 1.63X10+5 mg/l @ 25 °C.

Solubility in water: good

物理化学的性質

融点
108 · 108-112 °C (lit.)
沸点
111.7 · 111.7±23.0 °C(Predicted)
比重(密度)
1.37 · 1.37
屈折率
1.53 · 1.5300 (estimate)
貯蔵温度
Inert atmosphere,Room Temperature
溶解性
2 % · passes test 2%

化学的性質

化学的特性Thioacetamide is combustible, crystalline compound. Slight mercaptan odor.

化学性质融点112~114℃

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 5 件

Chemical: Ethanethioamide

Hazard Traits - Carcinogenicity

Status: Active Update: 30-09-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1779

Thioacetamide: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Ethanethioamide: Human health tier II assessment
Fire Hazards · 2 件

Flash point data on this compound are not available; it is probably combustible. (NTP, 1992)

Combustible.

Health Hazards · 1 件

SYMPTOMS: The symptoms following exposure to this compound may include skin and eye irritation, liver damage, fatigue, nausea, eczema, central nervous system depression, acidosis, vomiting, respiratory depression, hypotension, unconsciousness, tremors, convulsions, anorexia and conjunctivitis.

Hazards Summary · 1 件

Reports of degenerative liver changes following ingestion of the juice of oranges dipped for 2-5 seconds in 5% solution; Cirrhosis and other adverse changes (including tumors) of the liver observed in rats, mice, and dogs in feeding studies; [HSDB] May cause liver injury; A possible human carcinogen; [ICSC] A skin and eye irritant; [eChemPortal: ESIS] A skin and strong eye irritant; [Alfa Aesar MSDS]

Reactive GroupAmides and Imides

安全と保護具

Fire Fighting · 2 件

Fires involving this chemical should be controlled with a dry chemical, carbon dioxide, or Halon extinguisher. (NTP, 1992)

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from food and feedstuffs.
Storage Conditions · 1 件

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Cleanup Methods · 1 件

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

毒性情報

Interactions · 5 件

DISTRIBUTION OF PU /SRP: plutonium/ IN RATS WAS INFLUENCED BY ORAL ADMIN OF THIOACETAMIDE (300 MG/KG). RATS INJECTED IP WITH PLUTONIUM CITRATE RETAINED 71.5 & 23.6% OF RECOVERED ACTIVITY IN THE CARCASS & LIVER, RESPECTIVELY, WHEREAS RATS WHICH HAD BEEN TREATED WITH THIOACETAMIDE 24 HR PREVIOUSLY CONTAINED 35.8 & 59.5% OF THE PU IN THE CARCASS & LIVER RESPECTIVELY.

PHENOBARBITAL PRETREATMENT POTENTIATED HEPATIC NECROSIS PRODUCED BY THIOACETAMIDE.

ADRENALECTOMY PROTECTED RATS AGAINST THE HEPATOTOXIC ACTION OF THIOACETAMIDE INJECTED IP AT 200 MG/KG BW. THIS PROTECTIVE EFFECT COULD BE REVERSED BY HYDROCORTISONE GIVEN TWICE DAILY INTRAPERITONEALLY AT 0.5 TO 2.5 MG/RAT.

STROPHANTHIN-G PROTECTED RATS AGAINST LIVER NECROSIS CAUSED BY THIOACETAMIDE.

For more Interactions (Complete) data for THIOACETAMIDE (10 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from an log Kow of -0.26(2) and a regression-derived equation(3), indicates that thioacetamide is expected to have very high mobility in soil(SRC). Volatilization of thioacetamide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.4X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of thioacetamide from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 15 mm Hg(SRC), determined from a fragment constant method(5). Thioacetamide was not biodegraded by activated sludge after 5 days(6), and therefore may be resistant to biodegradation in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from an log Kow of -0.26(2) and a regression-derived equation(3), indicates that thioacetamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 6.4X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 days and 39 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Thioacetamide was not biodegraded by activated sludge after 5 days(7), and therefore may be resistant to biodegradation in aqueous systems(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thioacetamide, which has an estimated vapor pressure of 15 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase thioacetamide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 18 hours(SRC), calculated from its rate constant of 21X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Medical Surveillance · 1 件

PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/

Soil Adsorption/Mobility · 1 件

The Koc of thioacetamide is estimated as 17(SRC), using a log Kow of -0.26(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that thioacetamide is expected to have very high mobility in soil(SRC).

法規制情報

RCRA Requirements · 1 件

U218; As stipulated in 40 CFR 261.33, when thioacetamide, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

CERCLA Reportable Quantities · 1 件

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

安全データ

F
10
wgk
3
tsca
TSCA listed
rtecs
AC8925000
ridadr
2811
毒性
MLD orally in rats: 200 mg/kg (Ambrose)

化学と産業

薬理情報

Mechanism of Action · 3 件

Multiple injections of thioacetamide ... decrease the synthesis of cytochrome p450b and the amounts of its translatable mRNA.

A factor was isolated from /thioacetamide-induced/ fibrogenic rat liver which stimulates collagen synthesis in cultured fibrolblasts without affecting their rate of proliferation.

Altered transport of nuclear RNA sequences is an early response to carcinogens. Nuclear envelopes were isolated and assayed for nucleoside triphosphatase (NTPase) activity, on the premise that this enzymatic activity participates in RNA transport. A common feature of the action of ... thioacetamide ... at low doses without significant toxicity, was to increase nuclear envelopes NTPase activity and to increase RNA transport, as assessed by the appearance of rapiidly labeled RNA in the cytoplasm and by in vitro assay. The increases in NTPase were specific for the nuclear envelope fraction, and early toxic effects of higher doses initially masked the increases. The induced increases in nuclear envelope NTPase were long-lived. In contrast, increases in nuclear envelope NTPase were observed only during the regenerative phase of carbon tetrachloride intoxication; the CCl4-induced increase was short-lived and returned promptly to control levels. These changes in NTPase activity were not associated with parallel changes in phosphorylation/dephosphorylation of nuclear envelope proteins. Increases in nuclear envelope NTPase and alterations in RNA transport, without attendant nuclear replication, may relate to altered nuclear RNA restriction. This change in a regulatory phenomenon may make these cells more susceptible to further modification, potentially playing a role in the initiation phase of carcinogenesis.

Metabolism/Metabolites · 5 件

...THIOACETAMIDE IS METABOLIZED IN VIVO TO ACETAMIDE WHICH IS ITSELF CARCINOGENIC...ACETAMIDE IS THEN HYDROLYZED TO ACETATE...

THIOACETAMIDE, A PRE- OR PROCARCINOGEN, MUST UNDERGO BIOCHEMICAL METABOLIC ACTIVATION BY HOST. /FROM TABLE/

HEPATOTOXICITY OF THIOACETAMIDE MAY BE MEDIATED BY ITS METAB TO THIOACETAMIDE SULFINE WHICH IN TURN, IS METABOLIZED TO AN ULTIMATE TOXIC METABOLITE.

THIOACETAMIDE IS OXIDIZED TO THIOACETAMIDE S-OXIDE BY RAT LIVER MICROSOMES & BY A MIXED-FUNCTION OXIDASE SYSTEM.

For more Metabolism/Metabolites (Complete) data for THIOACETAMIDE (9 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 3 件

WHEN 5 MG (3)H-THIOACETAMIDE WERE ADMIN ORALLY IN DIET TO MALE ALBINO RATS... RADIOACTIVITY WAS FOUND IN ALL ORGANS EXAMINED (LIVER, KIDNEY & ADRENAL GLAND) & WAS HIGHEST IN LIVER.

WHOLE-BODY AUTORADIOGRAPHY SHOWED THAT AN IV DOSE OF ANTITHYROID AGENT, (35)S-THIOACETAMIDE, WAS TAKEN UP IN LIVER, KIDNEYS (MEDULLA), HEART MUSCLE, HARDERIAN GLANDS, SPLEEN, LYMPH NODES, & GI TRACT OF RATS. ABOUT 80% WAS EXCRETED IN 24-HR URINE.

THE DISTRIBUTION OF LABELED THIOACETAMIDE WAS STUDIED AS A FUNCTION OF TIME IN LIVER, KIDNEYS, PLASMA, AND MUSCLE OF RATS. THE DEVELOPMENT OF CENTRILOBULAR HEPATIC NECROSIS WAS FIRST OBSERVED 6 HOURS AFTER PEAK PLASMA LEVELS OF THIOACETAMIDE-S-OXIDE WERE OBTAINED (9 HOURS AFTER ADMINISTRATION OF THIOACETAMIDE).

用途と製造

Uses · 5 件

Used as a replacement for gaseous hydrogen sulfide in qualitative analysis; Used formerly as a stabilizer of motor fuel containing tetraethyl lead and mordant of seed grain (combined with mercury); [HSDB]

Petroleum Production and Refining [Category: Industry]

As replacement for gaseous hydrogen sulfide in qualitative analysis.

The addition of thioacetamide to 1,4-benzoquinone produces modest yields of 2-substituted 3a-Hydroxy-1,3-benzothiazol-6(3aH)-ones.

Stabilizer of motor fuel containing tetraethyl lead ... mordant of seed grain in combination with mercury /Former use/

U.S. Imports(1977) AT LEAST 4.54X10+5 G
U.S. Production · 2 件

(1977) AT LEAST 4.54X10+5 G

(1982) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.

Methods of ManufacturingPrepn: prepd by heating ammonium acetate and aluminum sulfide: Kindler, Finndorf, Ber 54, 1080 (1921); from acetonitrile + H2S: Kindler, Ann 431, 203 (1923); from acetamide + K3PS4: Schultz, Ranke, Arch Pharm 294, 82 (1961).
General Manufacturing InformationEthanethioamide: ACTIVE
応用分野 · 6 件

解説チオアセトアミド (英: Thioacetamide) とは、分子式C2H5NSで表される、チオアミドの一種の有機化合物です。 別名には、「アセトチオアミド」「エタンチオアミド」「アセトイミドチオ酸」などがあります。CAS登録番号は、62-55-5です。チオアセトアミド水溶液と多くの金属カチオンはそれぞれ対応する硫化物を作り、古典的定性分析で使われます。人体に対して有害な物質です。

用途染料、 医薬?医薬中間体、合成中間体、写真薬

説明Thioacetamide (TAA) is not known to occur in nature. It is prepared by heating ammonium acetate and aluminum sulfide.

使用Thioacetamide is a carcinogen, a hepatotoxicant. Thioacetamide induces acute chronic liver injury through the activation of protein synthesis of RNA, DNA, and gamma-glutamyl transpeptitase. Thioacetamide has been used in the synthesis of [emailprotected] nano-array core-shell structure.

一般的な説明Thioacetamide occurs as a colorless leaf-like material with aslight Sulfur-like odor. It is used as a substitute for HydrogenSulfide in the laboratory and as a stabilizer of motor fuel.

使用用途チオアセトアミドの主な用途は、染料、医薬品および医薬品中間体、合成中間体、写真・印刷薬品です。例えば、カドミウムイオンの溶液にチオアセトアミド水溶液を加えた後に加温することで、硫化カドミウムが得られます。この硫化カドミウムは、黄色顔料であるカドミウムイエローの主成分です。 このほか、チオアセトアミドは、古典的定性分析におけるの供給源であり、金属硫化物の沈殿試薬 (均質沈殿法) 、金属イオンの系統分析の分属試薬に使用されています。

調製方法 · 2 件

合成方法酢酸アンモニウムと硫化アルミニウムとの反応や,アセトニトリルと硫化水素との反応,またはアセトアミドの硫化反応で得られる

純化方法Crystallise the amide from absolute diethyl ether or *benzene. Dry it at 70o in a vacuum and store it over P2O5 at 0o under nitrogen. (It develops an obnoxious odour on storage, and absorption at 269nm decreases, hence it should be freshly recrystallised before use). [Beilstein 2 IV 565.]

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補足説明

定義ChEBI: Thioacetamide is a thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur. It has a role as a hepatotoxic agent. It is functionally related to an acetamide.

関連反応

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