Record Information |
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Version | 2.0 |
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Creation Date | 2009-06-22 16:08:28 UTC |
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Update Date | 2014-12-24 20:24:28 UTC |
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Accession Number | T3D1696 |
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Identification |
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Common Name | Butyronitrile |
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Class | Small Molecule |
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Description | Butyronitrile is a chemical compound of cyanide. |
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Compound Type | - Cyanide Compound
- Industrial/Workplace Toxin
- Nitrile
- Organic Compound
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 1-Cyanopropane | 1-Cyanopropane, butyronitrile | Butane nitrile | Butyric acid nitrile | Butyrylonitrile | N-butanenitrile | N-butanitrile | N-butyronitrile | n-C3H7CN | N-propyl cyanide | Propyl cyanide | Propylkyanid |
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Chemical Formula | C4H7N |
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Average Molecular Mass | 69.105 g/mol |
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Monoisotopic Mass | 69.058 g/mol |
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CAS Registry Number | 109-74-0 |
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IUPAC Name | butanenitrile |
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Traditional Name | butyronitrile |
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SMILES | CCCC#N |
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InChI Identifier | InChI=1S/C4H7N/c1-2-3-4-5/h2-3H2,1H3 |
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InChI Key | InChIKey=KVNRLNFWIYMESJ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as nitriles. Nitriles are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N. |
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Kingdom | Organic compounds |
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Super Class | Organic nitrogen compounds |
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Class | Organonitrogen compounds |
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Sub Class | Organic cyanides |
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Direct Parent | Nitriles |
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Alternative Parents | |
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Substituents | - Nitrile
- Carbonitrile
- Organopnictogen compound
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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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 | Colorless liquid. |
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Experimental Properties | Property | Value |
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Melting Point | -111.9°C | Boiling Point | Not Available | Solubility | 33 mg/mL at 25°C [RIDDICK,JA et al. (1986)] | LogP | Not Available |
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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 | splash10-00or-9000000000-21c1ab5518914c9ad298 | 2021-09-24 | 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 | splash10-00di-9000000000-c94896bd7f096e0c3bea | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-9000000000-5e3e755172188a95375f | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f6x-9000000000-d922d1b3163044da00af | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-9000000000-109de0539d7042dcd145 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-9000000000-375578187d1a0d0b9af1 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0f6x-9000000000-8371dc97c6622a149403 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-9000000000-baef1c6704ee82249101 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-9000000000-afb9ab058db4956adc39 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0uxu-9000000000-59e9a684943f6502bc50 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-9000000000-ca6676eceb57d5af0d73 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-40f0fb48265e0a0419a5 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-18462260b879a5709567 | 2021-10-12 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-002f-9000000000-2240795d5361b19d5e9d | 2014-09-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | Not Available | 2014-09-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | Not Available | 2014-09-23 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Oral (4) ; inhalation (4) ; dermal (4) |
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Mechanism of Toxicity | Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (5) |
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Metabolism | Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (4) |
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Toxicity Values | LD50: 50 mg/kg (Intraperitoneal, Rat) (1)
LD50: 28 mg/kg (Oral, Mouse) (1)
LD50: 200 mg/kg (Subcutaneous, Rat) (3)
LD50: 400 mg/kg (Dermal, Rabbit) (3)
LC50: 249 ppm over 1 hour (Inhalation, Mouse) (1) |
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Lethal Dose | 212 to 300 milligrams for an adult human (cyanide salts). (2) |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (4, 5) |
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Symptoms | Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (4, 5) |
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Treatment | Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (5) |
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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 | Not Available |
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PubChem Compound ID | 8008 |
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ChEMBL ID | Not Available |
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ChemSpider ID | 7717 |
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KEGG ID | Not Available |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 51937 |
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BioCyc ID | Not Available |
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CTD ID | C032723 |
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Stitch ID | Butyronitrile |
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PDB ID | Not Available |
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ACToR ID | 3523 |
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Wikipedia Link | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | T3D1696.pdf |
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General References | - Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
- Baselt RC and Cravey RH (1989). Disposition of Toxic Drugs and Chemicals in Man. 3rd ed. Chicago, IL.: Year Book Medical Publishers.
- Snyder, R (1990). Ethyl Browning's Toxicity and Metabolism of Industrial Solvents. 2nd ed. Volume II: Nitrogen and Phosphorus Solvents. Amsterdam-New York-Oxford: Elsevier.
- ATSDR - Agency for Toxic Substances and Disease Registry (2006). Toxicological profile for cyanide. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- Wikipedia. Cyanide poisoning. Last Updated 30 March 2009. [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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