Tetraethylthiuramdisulfid
DSF · TETD · Tts · disulfane · Disulfuram · Antabuse · TETRAETHYLTHIURAM DISULFIDE · Ttd
Identifikatoren & physikalische Daten
| CAS No. | 97-77-8 |
|---|---|
| Summenformel | C10H20N2S4 |
| Durchschnittliche Molmasse | 296,5 g/mol |
| Monoisotopische Masse | 296,05093334 g/mol |
| SMILES | CCN(CC)C(=S)SSC(=S)N(CC)CC |
| InChIKey | AUZONCFQVSMFAP-UHFFFAOYSA-N |
| PubChem CID | 3117 |
| ChEMBL | CHEMBL964 |
| ChEBI | CHEBI:4659 |
| EC No. | 202-607-8 |
| DTXSID | DTXSID1021322 |
| Lokaler Name | Tetraethylthiuramdisulfid |
Chemische & physikalische Eigenschaften
| XLogP | 3,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 121 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 201 |
| LogP (Verteilungskoeffizient) | 3.88log Kow= 3.881.93.9 |
| LogS | -4.86 |
| Geruch | Slight odor.Odorless |
| Geschmack | SLIGHTLY BITTER TASTE |
| Dichte | 1.27 at 68 °F (NTP, 1992) - Denser than waterwill sink1.301.3 g/cm³1.3 @25 °C |
| Color/Form | WHITE TO OFF-WHITE CRYSTALLINE POWDERLight-gray powderWhite, yellowish, or light-gray powder. |
| Löslichkeit | less than 0.1 mg/mL at 70 °F (NTP, 1992)4.09Sol in alc (3.82 g/100 ml), ether (7.14 g/100 ml), acetone, benzene, chloroform, carbon disulfideSoluble in aromaticIn water, 4.09 mg/L at 25 °C1.26e-02 g/L0.004g/l0.02 g/100 mL |
| Siedepunkt | 243 °F at 17 mmHg (NTP, 1992)117117 °C at 17 mm Hgat 2.3kPa: 117 °C117 °C @760 [mm Hg]117°C |
| Schmelzpunkt | 158 °F (NTP, 1992)71.571.5 °C71 °C69-71 °C (lit.) |
| Dampfdruck | 0 mmHg at 68 °F approximately (NTP, 1992)0.00087 [mmHg]0Pa at 25℃ |
| Physical Description | Tetraethylthiuram disulfide appears as odorless or almost odorless white or almost white to tan powder. Unpleasant taste with metallic or garlic aftertaste. pH of a solution obtained by shaking 1 g with 30 mL of water is 6 to 8. (NTP, 1992)Dry PowderGas VaporOther SolidLarge CrystalsWhite, yellowish, or light-gray powder with a slight odor.(fungicide)[NIOSH]WHITE-TO-GREY POWDER WITH CHARACTERISTIC ODOUR.White, yellowish, or light-gray powder with a slight odor. |
| Ionization Efficiency | Positive3.522.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Brechungsindex | 1.5500 (estimate) |
| Flammpunkt | 117°C/17mm |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Crystals, Crystalline Powder or Granules |
| pKa (Säurekonstante) | 0.86±0.50(Predicted) |
| Farbe | Light yellow |
| Geruch | lt. gray powd., sl. odor |
| Spezifische Wärmekapazität | Cp(liquid): 0.28 J/(g·K)Cp(gas): 0.17 J/(g·K), at 25℃ |
| Merck | 14,3364 |
| BRN | 1712560 |
| Henry-Konstante | 1.2×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidants. |
| InChI | 1S/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3 |
| InChIKey | AUZONCFQVSMFAP-UHFFFAOYSA-N |
| SMILES | CCN(CC)C(=S)SSC(=S)N(CC)CC |
| LogP (Verteilungskoeffizient) | 3.6 at 21℃ |
| CAS Datenbank | 97-77-8(CAS DataBase Reference) |
| NIST chemische Informationen | Disulfiram(97-77-8) |
| EPA chemische Informationen | Disulfiram (97-77-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]H317: May cause an allergic skin reaction [Warning Sensitization, Skin]H373 **: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P260, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P319, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), tetraethyl-Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), N,N,N',N'-tetraethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), N,N,N',N'-tetraethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11549Tetraethylthiuram disulfide: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), tetraethyl-: Human health tier II assessment |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992)Combustible. Finely dispersed particles form explosive mixtures in air. |
| Brandpotenzial | Combustible. |
| Gesundheitsgefahren | Excerpt from NIOSH Pocket Guide for Disulfiram:Exposure Routes: Inhalation, ingestion, skin and/or eye contactSymptoms: Irritation eyes, skin, respiratory systemsensitization dermatitislassitude (weakness, exhaustion), tremor, restlessness, headache, dizziness |
Anwendungen & Verwendung
Beschreibung
Das Tetraethylthiuramdisulfid bildet ein weißes, in Wasser unlösliches Pulver. Es wird als Medikament zur Behandlung von chronischem Alkoholmißbrauch verwendet. Die pharmakologische Wirkung wurde 1948 von den Chemikern Hald, Jakobson und Larsen entdeckt. Die Einnahme von 1,5 g Disulfiram per os sensibilisiert den Körper für etwa 8 Tage gegen Alkohol. Bereits geringste Mengen Alkohol führen dann zu heftigen körperlichen Reaktionen. Die häufigsten Symptome sind Schwindel, Kopfschmerzen, Brechreiz, ausgeprägte Übelkeit, Tachykardie, Hypotonie und starke körperliche Schwäche. Die Wirkung von Disulfiram beruht auf der Hemmung des Enzyms Aldehydoxidase, welches das erste Oxidationsprodukt des Alkohols, den Acetaldehyd, im Körper zu Essigsäure abbauen soll. Durch die Hemmung des Enzyms kommt es zu einer Anreicherung von Acetaldehyd im Körper, wodurch die genannten Symptome ausgelöst werden. Disulfiram ist kontraindiziert bei Diabetes mellitus sowie bei Herz- und Kreislaufinsuffizienz.
Beschreibung
Disulfiram was first synthesized in the 1800s to improve the manufacturing process of rubber. A physician working in a rubber factory plant first observed in 1937 that factory workers who were exposed to disulfiram were intolerant to ethanol. In the 1940s, two scientists rediscovered the disulfiram– ethanol effects while researching antiparasitic therapies. This finding eventually led to the approval of the medication to be used as an ethanol deterrent by the Food and Drug Administration in 1951.
Verwenden
Disulfiram is a copper and zinc chelator and an irreversible inhibitor of aldehyde dehydrogenase (IC50 = 0.1 mM) that has been indicated for the treatment of alcohol dependence. It also inhibits the copper-dependent enzyme dopamine β-hydroxylase, which prevents the breakdown of dopamine and has been considered as a treatment for cocaine dependence. When in complex with copper, disulfiram has been shown to inhibit purified 20S proteasome (IC50 = 7.5 μM) and 26S proteasome (IC50 = 20 μM) from MDA-MB-0231 breast cancer cells. Because disulfiram targets the ubiquitin-proteasome pathway, it has been investigated as an anti-cancer agent. Furthermore, at 250 nM it has been shown to induce reactive oxygen species, to activate JNK and p38 pathways, and to inhibit NF-κB activity, which suppresses self-renewal in cancer stem cells.