| Record Information |
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| Version | 2.0 |
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| Creation Date | 2009-03-06 18:58:13 UTC |
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| Update Date | 2014-12-24 20:21:16 UTC |
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| Accession Number | T3D0176 |
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| Identification |
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| Common Name | Carbon disulfide |
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| Class | Small Molecule |
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| Description | Carbon disulfide is found in kohlrabi. Obsolete fumigant against insects in stored grain and potatoes. |
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| Compound Type | - Food Toxin
- Industrial/Workplace Toxin
- Metabolite
- Natural Compound
- Organic Compound
- Pollutant
- Solvent
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| Chemical Structure | |
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| Synonyms | | Synonym | | Carbon bisulfide | | Carbon bisulphide | | Carbon disulphide | | Carbon disulphide, BSI | | Carbon sulfide (CS2) | | Dithiocarbonic anhydride |
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| Chemical Formula | CS2 |
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| Average Molecular Mass | 76.141 g/mol |
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| Monoisotopic Mass | 75.944 g/mol |
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| CAS Registry Number | 75-15-0 |
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| IUPAC Name | methanedithione |
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| Traditional Name | carbon disulfide |
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| SMILES | S=C=S |
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| InChI Identifier | InChI=1S/CS2/c2-1-3 |
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| InChI Key | InChIKey=QGJOPFRUJISHPQ-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of inorganic compounds known as other non-metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen belongs to the class of other non-metals. |
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| Kingdom | Inorganic compounds |
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| Super Class | Homogeneous non-metal compounds |
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| Class | Other non-metal organides |
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| Sub Class | Other non-metal sulfides |
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| Direct Parent | Other non-metal sulfides |
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| Alternative Parents | |
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| Substituents | - Other non-metal sulfide
- Inorganic sulfide
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| Molecular Framework | Not Available |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Liquid |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | -111.6°C | | Boiling Point | 46.3°C (115.3°F) | | Solubility | 2.16 mg/mL at 20°C | | LogP | 1.94 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-9000000000-1be1dd1539f07de91257 | 2017-09-01 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-9000000000-c32b774f5ef5f9e3b3b5 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-9000000000-c32b774f5ef5f9e3b3b5 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-9000000000-c32b774f5ef5f9e3b3b5 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-f8b0b78f7785ba1a8d02 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-f8b0b78f7785ba1a8d02 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9000000000-f8b0b78f7785ba1a8d02 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-9000000000-05fa4e3edea82fd450a4 | 2021-09-23 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-9000000000-05fa4e3edea82fd450a4 | 2021-09-23 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-9000000000-05fa4e3edea82fd450a4 | 2021-09-23 | View Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-004i-9000000000-4fd31585d55b0b9843c4 | 2014-09-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | Not Available | 2014-09-23 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Inhalation (12) ; oral (12) ; dermal (12) ; eye contact (12) |
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| Mechanism of Toxicity | Carbon disulfide is a potent nerve toxin and also affect liver enzymes, particularly those related to lipid metabolism. The increases in serum cholesterol that are sometimes seen following carbon disulfide exposure may be a result of increased hepatic cholesterol synthesis. The primary target of carbon disulfide appears to be the nervous system. Neurophysiological and behavioral effects as well as pathomorphology of peripheral nervous system structures have been reported in humans. Moreover, carbon disulfide metabolites of the thiocarbamate type inhibit aldehyde anhydrase. (11, 7) |
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| Metabolism | Nitrogenase reduces carbon disulfide and can also be inhibited by this toxin. Carbon disulfide binds (in the form of AL CS2) mainly to hemoglobin and to a small extent to other blood proteins, such as albumin and gamma-globulin. Carbon disulfide is bioactivated by cytochrome P-450 to an unstable oxygen intermediate. The intermediate may either spontaneously degrade to atomic sulfur and carbonyl sulfide or hydrolyze to form atomic sulfur and monothiocarbonate. The atomic sulfur generated in these reactions may either covalently bind to macromolecules or be oxidized to products such as sulfate. The carbonyl sulfide formed may be converted to monothiocarbonate by carbonic anhydrase. Monothiocarbonate may further spontaneously degrade, regenerating carbonyl sulfide or forming carbon dioxide and sulfide bisulfide ion (HS-). The HS- formed can subsequently be oxidized to sulfate or other nonvolatile metabolites. Dithiocarbamates are the products of the reaction of carbon disulfide with amino acids. Most of the carbon disulfude absorbed is metabolized. Small traces of unchanged can be found in the urine. Carbon disulfide or carbonyl sulfide can conjugate with endogenous glutathione to yield thiazolidine-2-thione-4-carboxylic acid and 2-oxythiazolidine-4-carboxylic acid, respectively. Carbonic anhydrase 2 mediates the metabolism of carbon disulfide. (11, 2, 3, 4, 5, 6) |
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| Toxicity Values | LD50: 3020 mg/kg/day (Oral, Mouse) (11) |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Several industries use carbon disulfide as a raw material to make such things as rayon, cellophane, and carbon tetrachloride. Exposure to carbon disulfide can results from breathing air, drinking water, or eating foods that contain it. One can also be exposed by skin contact with soil, water, or other substances that contain it. (11) |
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| Minimum Risk Level | Chronic Inhalation: 0.3 ppm (11)
Acute Oral: 0.01 mg/kg/day (11) |
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| Health Effects | Following inhalation, subtle and transient changes in pulmonary function can be manifested as reduced vital capacity and decreased partial pressure of arterial oxygen. Patients can developed normochromic and normocytic anemia, eosinopenia, and an increase in reticulocyte cell numbers after oral exposure . Carbon disulfide poisoning can result in central nervous system depression, coma, respiratory paralysis, and death. It also may accelerate coronary artery disease. Peripheral neuropathies, cranial nerve dysfunction, and neuropsychiatric changes are present in over 70% of chronic carbon sulfide victims. (11) |
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| Symptoms | Dizziness, headache, nausea, shortness of breath, vomiting, weakness, irritability and hallucination can result from inhalation, ingestion or skin exposure to carbon disultfide. Skin and eye exposure can lead to pain, redness. Moreover, dermal exposure can lead to dryness of the skin; the carbon disulfide may be absorbed. Weak pulse, palpitations, fatigue, weakness in the legs, unsteady gait, vertigo, hyperesthesia, agitation, mania, hallucinations of sight, hearing, taste, and smell in acute are other symtoms of carbon disulfide poisoning. (12, 8) |
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| Treatment | Following oral exposure, administer charcoal as a slurry (240 mL water/30 g charcoal). Consider gastric lavage after ingestion of a potentially life-threatening amount of poison if it can be performed soon after ingestion (generally within 1 hour). Intravenous urea (0.5 to 1.5 g/kg) has been recommended to inactivate free carbon disulfide in the blood. The efficacy of this treatment is unknown. Following inhalation exposure, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. If the exposure occurred through eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If the exposure occurred through dermal contact, remove contaminated clothing and wash exposed area thoroughly with soap and water. (9) |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB36574 |
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| PubChem Compound ID | 6348 |
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| ChEMBL ID | CHEMBL1365180 |
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| ChemSpider ID | 6108 |
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| KEGG ID | C19033 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 23012 |
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| BioCyc ID | CPD-844 |
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| CTD ID | Not Available |
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| Stitch ID | Carbon disulfide |
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| PDB ID | Not Available |
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| ACToR ID | Not Available |
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| Wikipedia Link | Carbon disulfide |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Link |
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| General References | - Sams C, Loizou GD, Cocker J, Lennard MS: Metabolism of ethylbenzene by human liver microsomes and recombinant human cytochrome P450s (CYP). Toxicol Lett. 2004 Mar 7;147(3):253-60. [15104117 ]
- Haritos VS, Dojchinov G: Carbonic anhydrase metabolism is a key factor in the toxicity of CO2 and COS but not CS2 toward the flour beetle Tribolium castaneum [Coleoptera: Tenebrionidae]. Comp Biochem Physiol C Toxicol Pharmacol. 2005 Jan;140(1):139-47. [15792633 ]
- Masuda Y, Yasoshima M, Nakayama N: Early, selective and reversible suppression of cytochrome P-450-dependent monooxygenase of liver microsomes following the administration of low doses of carbon disulfide in mice. Biochem Pharmacol. 1986 Nov 15;35(22):3941-7. [3778518 ]
- Ryle MJ, Lee HI, Seefeldt LC, Hoffman BM: Nitrogenase reduction of carbon disulfide: freeze-quench EPR and ENDOR evidence for three sequential intermediates with cluster-bound carbon moieties. Biochemistry. 2000 Feb 8;39(5):1114-9. [10653657 ]
- Seefeldt LC, Rasche ME, Ensign SA: Carbonyl sulfide and carbon dioxide as new substrates, and carbon disulfide as a new inhibitor, of nitrogenase. Biochemistry. 1995 Apr 25;34(16):5382-9. [7727396 ]
- Lam CW, DiStefano V: Characterization of carbon disulfide binding in blood and to other biological substances. Toxicol Appl Pharmacol. 1986 Nov;86(2):235-42. [3787622 ]
- Schreiner E, Freundt KJ: Behaviour of epoxide hydrolase, glutathione S-transferase, alcohol dehydrogenase, and aldehyde dehydrogenase, respectively, under the influence of carbon disulfide studies with rats in vivo and in vitro. G Ital Med Lav. 1984 May-Jul;6(3-4):131-3. [6242047 ]
- Thompson TS and Vorster SJ (2000). Attempted suicide by ingestion of methoxychlor. J Anal Toxicol 24:377-380.
- Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
- Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
- ATSDR - Agency for Toxic Substances and Disease Registry (1996). Toxicological profile for carbon disulfide. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- International Programme on Chemical Safety (IPCS) INCHEM (2000). Poison Information Monograph for Carbon Disulfide. [Link]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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