Tetraethylthiuramdisulfid

Bezeichnung:Tetraethylthiuramdisulfid

CAS-Nr97-77-8

Englisch Name:Disulfiram

CBNumberCB0476519

SummenformelC10H20N2S4

Molgewicht296.54

MOL-Datei97-77-8.mol

Synonyma

Disulfiram

Tetraethylthiuramdisulfid

Tetraethylthioperoxydicarbons?urediamid

Tetraethylthiuramdisulfid physikalisch-chemischer Eigenschaften

Schmelzpunkt	69-71 °C (lit.)
Siedepunkt	117°C
Dichte	1.27
Dampfdruck	0Pa at 25℃
Brechungsindex	1.5500 (estimate)
Flammpunkt	117°C/17mm
storage temp.	2-8°C
Löslichkeit	0.004g/l
pka	0.86±0.50(Predicted)
Aggregatzustand	Crystals, Crystalline Powder or Granules
Farbe	Light yellow
Geruch (Odor)	lt. gray powd., sl. odor
Wasserlöslichkeit	0.02 g/100 mL
Merck	14,3364
BRN	1712560
Expositionsgrenzwerte	ACGIH: TWA 2 mg/m3 NIOSH: TWA 2 mg/m3
Stabilität	Stable. Incompatible with strong oxidants.
InChIKey	AUZONCFQVSMFAP-UHFFFAOYSA-N
LogP	3.6 at 21℃
CAS Datenbank	97-77-8(CAS DataBase Reference)
NIST chemische Informationen	Disulfiram(97-77-8)
IARC	3 (Vol. 12, Sup 7) 1987
EPA chemische Informationen	Disulfiram (97-77-8)

Sicherheit

Kennzeichnung gefährlicher	Xn,N
R-Sätze:	22-43-48/22-50/53
S-Sätze:	24-37-60-61
OEB	B
OEL	TWA: 2 mg/m3 [Precautions should be taken to avoid concurrent exposure to ethylene dibromide.]
RIDADR	UN 3077 9/PG 3
WGK Germany	3
RTECS-Nr.	JO1225000
TSCA	Yes
HazardClass	9
PackingGroup	III
HS Code	29303000
Giftige Stoffe Daten	97-77-8(Hazardous Substances Data)
Toxizität	LD50 orally in rats: 8.6 g/kg (Child, Cramp)

Gefahreninformationscode (GHS)

Disulfiram Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
WEISSESBIS GRAUES PULVER MIT CHARAKTERISTISCHEM GERUCH.
PHYSIKALISCHE GEFAHREN
Staubexplosion der pulverisierten oder granulierten Substanz in Gemischen mit Luft möglich. Die trockene Substanz kann durch Verwirbeln, Druckluft, Fließen usw. elektrostatisch aufgeladen werden.
CHEMISCHE GEFAHREN
Zersetzung beim Verbrennen unter Bildung giftiger und ätzender Rauche mit Stickstoffoxiden und Schwefeloxiden. Reagiert sehr heftig mit starken Oxidationsmitteln. Greift Kupfer an.
ARBEITSPLATZGRENZWERTE
TLV: (als TWA) 2 mg/m? Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2005).
MAK: 2 mg/m? (Einatembare Fraktion) Spitzenbegrenzung: überschreitungsfaktor II(8); Sensibilisierung der Haut; Schwangerschaft: Gruppe D; (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation des Staubes und durch Verschlucken.
INHALATIONSGEFAHREN
Verdampfung bei 20°C vernachlässigbar; eine gesundheitsschädliche Partikelkonzentration in der Luft kann jedoch beim Dispergieren schnell erreicht werden, besonders als Pulver.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Hautkontakt kann zu Hautsensibilisierung führen. Möglich sind Auswirkungen auf endokrines System, Leber, Nervensystemund Schilddrüse mit nachfolgenden Funktionsstörungen. Tierversuche zeigen, dass die Substanz möglicherweise fruchtbarkeitsschädigend oder entwicklungsschädigend wirken kann.
LECKAGE
Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. NICHT in die Umwelt gelangen lassen. Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel.
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R43:Sensibilisierung durch Hautkontakt möglich.
R48/22:Gesundheitsschädlich: Gefahr ernster Gesundheitsschäden bei längerer Exposition durch Verschlucken.
R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
S-Sätze Betriebsanweisung:
S24:Berührung mit der Haut vermeiden.
S37:Geeignete Schutzhandschuhe tragen.
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
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.
Chemische Eigenschaften
yellow-white crystals or grey powder
Originator
Esperal,Millot Solac,France,1950
Verwenden
Alcohol deterrent;Dopamine beta-hydroxylase inhibitor;For the treatment and management of chronic alcoholism.
Verwenden
It is used as rubber accelerator; vulcanizer; seed disinfectant; fungicide; alcohol deterrent.
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.
Definition
ChEBI: An organic disulfide that results from the formal oxidative dimerisation of N,N-diethyldithiocarbamic acid. A multi-enzyme inhibitor that is used in alcohol aversion therapy and also exhibits anticancer properties.
Manufacturing Process
Disulfiram may be made by the reaction of diethyl amine with carbon disulfide in the presence of sodium hydroxide. The (C2H5)2NCSSNa intermediate is oxidatively coupled using hydrogen peroxide to give disulfiram.
Trademarks
Antabuse (Odyssey) .
Therapeutic Function
Alcohol deterrent
Allgemeine Beschreibung
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.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
Disulfiram is sensitive to light. Disulfiram is incompatible with strong acids, strong oxidizers and nitrosating agents (e.g. N-Nitrosodiphenylamine). .
Hazard
Toxic symptoms when ingested with alcohol; animal teratogen. Vasodilation and nausea. Questionable carcinogen.
Health Hazard
Disulfiram affects the central nervous system, thyroid, and skin; in combination with alcohol it causes an “Antabusealcohol” syndrome.
Small doses of disulfiram reportedly can cause effects on thyroid iodine uptake and thyroid gland hypertrophy. It may also produce dermatitis and acneform rashes.
Brandgefahr
Flash point data for Disulfiram are not available; however, Disulfiram is probably combustible.
Flammability and Explosibility
Not classified
Biologische Aktivität
Inhibitor of aldehyde dehydrogenase that displays antialcoholism activity. Shown to reversibly stimulated Ca 2+ -ATPase activity and inhibit V-ATPase (EC 50 = 26 μ M). Also inhibits expression of MMP-2 and MMP-9 and displays anti-invasive activity.
Kontakt-Allergie
TETD is a rubber accelerator of the thiuram group, contained in “thiuram mix.” It can cross-react with other thiurams, especially TMTD. TETD is used to aid those trying to break their dependence on alcohol. The disulfiram-alcohol reaction is not allergic but due to the accumulation of toxic levels of acetaldehyde. The implanted drug can, however, lead to local or generalized dermatitis, for example ingested disulfiram, mainly in previously rubber-sensitized patients. As an adjunctive treatment of alcoholism, it caused occupational contact dermatitis in a nurse.
Clinical Use
Adjunct in the treatment of chronic alcohol dependence
Sicherheitsprofil
A human poison by ingestion. An experimental poison by intraperitoneal route. Toxic symptoms when accompanied by ingestion of alcohol. Human systemic effects by ingestion: jaundtce, joint changes. An experimental teratogen. Other experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic data. See also THIRAM.
mögliche Exposition
AgriculturalChemical; Drug, Tumorigen, Mutagen; ReproductiveEffector; Human Data; Hormone, Primary Irritant. Somethiurams have been used as rubber components. Disulfiramis used as an accelerator in compounding natural, styrenebutadiene, and Neoprene? rubbers as a rubber acceleratorand vulcanizer; as a seed disinfectant and fungicide; in therapy; as an alcohol deterrent; in adhesives.
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs
Alcohol: risk of severe disulfiram reaction.
Anticoagulants: enhanced anticoagulant effect with coumarins.
Antiepileptics: inhibition of metabolism of fosphenytoin and phenytoin (increased risk of toxicity).
Paraldehyde: increased risk of toxicity with paraldehyde.
Erste Hilfe
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Note: For alcohol/disulfiram or ethylene dibromide/disulfiram reaction, remove the person from exposure. Begin rescue breathing (using universal precautions, includingresuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility.
Carcinogenicity
In a lifetime carcinogenicity bioassay, disulfiram was not carcinogenic in either rats or mice when fed in the diet. The highest doses were 600 ppm in rats and 2000ppm in mice.
Increased fetal resorptions, but no teratogenic effects, were seen in rats exposed at 100mg/kg/day from day 3 of gestation. A weak genotoxic response was observed in mice treated in vivo as evidenced by an increase in sister chromatid exchanges in bone marrow and spermatogonial cells.9
The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) is 2mg/m3.
Stoffwechsel
Disulfiram is rapidly reduced to diethyldithiocarbamate, mainly by the glutathione reductase system in erythrocytes; reduction may also occur in the liver.
Diethyldithiocarbamate is metabolised in the liver to its glucuronide and methyl ester and to diethylamine, carbon disulfide, and sulfate ions. Metabolites are excreted mainly in the urine; carbon disulfide is exhaled in the breath.
Lager
+4°C
Versand/Shipping
Toxic solids, flammable, organic, n.o.s. requiresa shipping label of “POISONOUS/TOXIC MATERIALS.”They fall into Hazard Class 6.1.
Toxicity evaluation
Disulfiram has multiple mechanisms of toxicity. Its most welldefined action is inhibition of aldehyde dehydrogenase, which thereby diminishes the breakdown of acetaldehyde. Accumulation of carbon disulfide, a disulfiram metabolite, as well as inhibition of dopamine-b-hydroxylase has also been associated with its toxicity in particular related to use for cocaine dependence.

Disulfiram Upstream-Materialien And Downstream Produkte

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