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97-77-8

Basic Information
CAS No.: 97-77-8
Name: Disulfiram
Article Data: 79
Molecular Structure:
Molecular Structure of 97-77-8 (Disulfiram)
Formula: C10H20N2S4
Molecular Weight: 296.546
Synonyms: NCI-C02959;Antiaethan;155-01-1;Contralin;Bis(N,N-diethylthiocarbamoyl) disulfide;Aversan;Thiuram disulfide, tetraethyl-;Averzan;Tiuram;Antaetil;anti-Ethyl;Dupon 4472;Thiuram E;Ekagom DTET;Bis((diethylamino)thioxomethyl) disulfide;tetraethylthiuram disulphide;Anthethyl;tetraethylthioperoxydicarbonic diamide;Ethyldithiourame;Soxinol TET;Tetraetil;Refusal [Netherlands];Abstensil;Bis((diethylamino)thioxomethyl)disulphide;Ethyl thiurad;Antethyl;Tetraethylthiuram;N,N,N,N-Tetraethylthiuram disulphide;Tetraethylthiuran disulfide;Disulfiram [BAN:INN:JAN];Disulfiram (JP14/USP);Ethyl Thiudad;Exhorran;Antetan;N,N,N,N-tetraethylthiuram disulfide;
EINECS: 202-607-8
Density: 1.205 g/cm3
Melting Point: 69-71 °C(lit.)
Boiling Point: 369.023 °C at 760 mmHg
Flash Point: 176.979 °C
Solubility: 0.02 g/100 mL in water
Appearance: yellow-white crystals or grey powder
Hazard Symbols: HarmfulXn,DangerousN
Risk Codes: 22-43-48/22-50/53
Safety: 24-37-60-61
Transport Information: UN 3077 9/PG 3
PSA: 121.26000
LogP: 3.62120
Synthetic route
147-84-2

Diethyldithiocarbamic acid

97-77-8

disulfiram

Conditions
ConditionsYield
With oxygen In ethanol at 20 - 30℃; under 3000.3 Torr; for 0.1h; Time; Flow reactor;99.8%
With 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine In ethanol; water at 40℃; for 0.5h; Temperature;98%
With morpholine; iodine In tetrahydrofuran; benzene at 10 - 20℃; for 0.25h;97%
109-89-7

diethylamine

97-77-8

disulfiram

Conditions
ConditionsYield
With triphenyl antimony oxide In acetonitrile for 24h; Ambient temperature;99%
75-15-0

carbon disulfide

109-89-7

diethylamine

97-77-8

disulfiram

Conditions
ConditionsYield
With oxygen In isopropyl alcohol at 50℃; under 1275.13 Torr; for 1.5h; Autoclave;98.5%
Stage #1: carbon disulfide; diethylamine With haematoxylin In ethanol at 20 - 30℃; for 0.1h;
Stage #2: In ethanol for 0.0333333h; Temperature; Irradiation;
98.99%
With carbon tetrabromide In N,N-dimethyl-formamide at 20℃; for 1h; Cooling with ice;96%
148-18-5

sodium N,N-diethyldithiocarbamate

97-77-8

disulfiram

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide In dichloromethane at 20℃; for 2h;96%
With iodine In methanol at 0℃;95%
With oxygen; sodium hydroxide In water at 25℃; for 1.08333h; pH=10; Kinetics; pH-value; Reagent/catalyst;94%
548761-51-9

N,N-diethyl-S-(α,α-dimethyl-α-acetic acid)dithiocarbamate

188526-94-5

N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl

A

97-77-8

disulfiram

B

654636-62-1

N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide

Conditions
ConditionsYield
In ethanol at 20℃; for 4h; Product distribution / selectivity; Inert atmosphere; Photolysis;A n/a
B 90%
112296-52-3

diethylammonium oxotrithiotungstate

A

W2O2(μ-S)2(S2CNEt2)2

B

97-77-8

disulfiram

Conditions
ConditionsYield
With carbon disulfide In N,N-dimethyl-formamide byproducts: H2S; refluxing (4 h); addn. of 2-propanol and ether, filtn., crystn. (room temp., overnight), washing (water, ethanol, ether), recrystn. (CH2Cl2/petroleum ether); elem. anal.;A 38%
B n/a

diethylammonium tetrathiotungstate(VI)

A

W2OS(μ-S)2(S2CNEt2)2

B

97-77-8

disulfiram

Conditions
ConditionsYield
With carbon disulfide; air In N,N-dimethyl-formamide byproducts: H2S; refluxing (4 h) in presence of air; addn. of 2-propanol and ether, filtn., crystn. (room temp., overnight), washing (water, ethanol, ether), recrystn. (CH2Cl2/petroleum ether), chromy. (silica gel, Ch2Cl2/petroleum ether 75:25); elem. anal.;A 30%
B n/a

diethylammonium tetrathiotungstate(VI)

A

W2S2(μ-S)2(S2CNEt2)2

B

97-77-8

disulfiram

Conditions
ConditionsYield
With carbon disulfide In N,N-dimethyl-formamide byproducts: H2S; N2 atmosphere, refluxing (absence of light, 4 h); addn. of 2-propanol and ether to the cold soln., filtn., crystn. (room temp., 24 h), washing (water, ethanol, ether), recrystn. (CH2Cl2/petroleum ether), chromy. (silica gel, CH2Cl2/petroleum ether 75:25); elem. anal.;A 28%
B n/a
75-15-0

carbon disulfide

3768-61-4

N,N,N',N'-tetraethylthioamine

97-77-8

disulfiram

3768-61-4

N,N,N',N'-tetraethylthioamine

97-77-8

disulfiram

Conditions
ConditionsYield
With carbon disulfide
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    Name: Tetraethylthiuram disulfide Synonyms: bis(diethylthiocarbamoyl) disulfide; disulfiram; tetraethylthiuram disulphide; accelerator tetd; bis (diethylthiocarbamyl) disulfide; tetraethyl thiuram disulfide; ethylthiudad; ethyltuex; etyl tuex; exhor

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    Product Name: Disulfiram CAS: 97-77-8 MF: C10H20N2S4 MW: 296.54 EINECS: 202-607-8 Mol File: 97-77-8.mol Disulfiram Structure Disulfiram Chemical Properties Melting point 69-71 °C (lit.) Boiling point 117°C density

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    ISO9001 1.Product name: DISULFIRAM ( USP26) 2.CAS No. 97-77-8 3.MF: C10H20N2S4 4.Assay: 98-102% 5.Appearance: Off-white crystal Appearance:off-white crystal Storage:Store in dry and cool place with good seal Package:25kg/fibre drum Applicati

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History

The researchers Erik Jacobsen, Jens Hald, and Keneth Ferguson from the Danish drug company Medicinalco discovered the drug's action in 1948  by accident . The substance was intended to provide a remedy for parasitic infestations; however, workers testing the substance on themselves reported severe symptoms after alcohol consumption.

Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 12 , 1976,p. 85.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); No Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-16 ,1979. . Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 2 mg/m3
ACGIH TLV: TWA 2 mg/m3; Not Classifiable as a Human Carcinogen
DFG MAK: 2 mg/m3

Specification

The Disulfiram , with cas registry number of 97-77-8, belongs to the classification codes of (1) Acaricide ; (2) Agricultural Chemical ; (3) Alcohol deterrents ; (4) Central Nervous System Agents ; (5) Drug / Therapeutic Agent ; (6) Enzyme inhibitors ; (7) Fungicide, bactericide, wood preservative ; (8) Immunomodulator ; (9) Reproductive Effect ; (10) Skin / Eye Irritant. It is also called TETD ; Bis(diethylthiocarbamoyl) disulfide ; Tetraethylthiuram disulfide . Its IUPAC name is diethylcarbamothioylsulfanyl N,N-diethylcarbamodithioate . And its systematic name is called 1,1',1'',1'''-[disulfanediylbis(carbonothioylnitrilo)]tetraethane . Its trade names include Antabuse and Antabus . Among all the names, its superlist name include Disulfide, bis(diethylthiocarbamoyl) ; Disulfiram ; Tetraethylthiuram disulfide ; Tetraethylthiuram disulphide ; Thioperoxydicarbonic diamide, tetraethyl- . Disulfiram is stable but incompatible with strong oxidants.

Physical properties of Disulfiram are: (1) ACD/LogP: 3.88 ; (2) # of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 3.88 ; (4) ACD/LogD (pH 7.4): 3.88 ; (5) ACD/BCF (pH 5.5): 523.35 ; (6) ACD/BCF (pH 7.4): 523.36 ; (7) ACD/KOC (pH 5.5): 3074.04 ; (8) ACD/KOC (pH 7.4): 3074.11 ; (9) #H bond acceptors: 2 ; (10) #H bond donors: 0 ; (11) #Freely Rotating Bonds: 7 ; (12) Index of Refraction: 1.619 ; (13) Molar Refractivity: 86.39 cm3 ; (14) Molar Volume: 246 cm3 ; (15) Surface Tension: 56.9 dyne/cm ; (16) Density: 1.205 g/cm3 ; (17) Flash Point: 177 °C ; (18) Enthalpy of Vaporization: 61.57 kJ/mol ; (19) Boiling Point: 369 °C at 760 mmHg ; (20) Vapour Pressure: 1.22E-05 mmHg at 25°C.

Preparation of Disulfiram : This chemical could be prepared from oxidation of sodium diethyldithiocarbamate with iodine :
2 NaS2CNEt2 + I2 → Et2NC(S)S-SC(S)NEt2 + 2 NaI (Et = C2H5)

Uses of Disulfiram : This product has been used as a drug to cure chronic alcoholism. It is first discovered in 1948. At present, it has been found that it may be used in cancer therapy and cocaine dependence.

When you are using this chemical, please be cautious about it as the following:
The Disulfiram is harmful if swallowed and very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. So, remember wear suitable gloves and avoid contact with skin. After use it,keep it in the container and avoid release to the environment. Its container must be disposed of as hazardous waste.

You can still convert the following datas into molecular structure:
(1) SMILES:S=C(SSC(=S)N(CC)CC)N(CC)CC ;
(2) InChI:InChI=1/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3;
(3) InChIKey:AUZONCFQVSMFAP-UHFFFAOYAF

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 150mg/kg (150mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

GASTROINTESTINAL: NAUSEA OR VOMITING
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 230, 1969.
dog LDLo oral 3500mg/kg (3500mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: ATAXIA
Acta Pharmacologica et Toxicologica. Vol. 8, Pg. 305, 1952.
human LDLo oral 160mg/kg (160mg/kg) BEHAVIORAL: COMA

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE

LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"
British Medical Journal. Vol. 2, Pg. 94, 1977.
man LDLo oral 150mg/kg/6W-I (150mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" Archives of Internal Medicine. Vol. 143, Pg. 1271, 1983.
man TDLo oral 150mg/kg/6W-I (150mg/kg) MUSCULOSKELETAL: JOINTS Arthritis and Rheumatism. Vol. 25, Pg. 1494, 1982.
man TDLo oral 450mg/kg/6W-I (450mg/kg) BRAIN AND COVERINGS: ENCEPHALITIS

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
American Journal of Gastroenterology. Vol. 93, Pg. 830, 1998.
mouse LD50 intraperitoneal 75mg/kg (75mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 oral 1980mg/kg (1980mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 112, Pg. 36, 1957.
mouse LD50 subcutaneous 2600mg/kg (2600mg/kg)   Drugs in Japan Vol. -, Pg. 523, 1995.
rabbit LD50 oral 1800mg/kg (1800mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: ATAXIA
Acta Pharmacologica et Toxicologica. Vol. 8, Pg. 305, 1952.
rat LD subcutaneous > 4gm/kg (4000mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 8, Pg. 305, 1952.
rat LD50 intraperitoneal 248mg/kg (248mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Journal de Pharmacologie. Vol. 9, Pg. 35, 1978.
rat LD50 oral 500mg/kg (500mg/kg)   Archiv fuer Toxikologie. Vol. 22, Pg. 12, 1966.
women LDLo oral 90mg/kg/18D-I (90mg/kg) BEHAVIORAL: COMA

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Deutsche Medizinische Wochenschrift. Vol. 118, Pg. 1355, 1993.
women TDLo oral 90mg/kg/18D-I (90mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" Journal of Clinical Psychiatry. Vol. 46, Pg. 67, 1985.
women TDLo oral 140mg/kg/2W (140mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Southern Medical Journal. Vol. 80, Pg. 1577, 1987.