| Record Information |
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| Version | 1.0 |
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| Creation Date | 2009-06-22 16:08:25 UTC |
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| Update Date | 2016-11-09 01:08:32 UTC |
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| Accession Number | CHEM001423 |
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| Identification |
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| Common Name | n-Butyl isocyanate |
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| Class | Small Molecule |
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| Description | n-Butyl isocyanate is a chemical compound of cyanide. |
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| Contaminant Sources | - HPV EPA Chemicals
- OECD HPV Chemicals
- STOFF IDENT Compounds
- T3DB toxins
- ToxCast & Tox21 Chemicals
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| Contaminant Type | - Cyanide Compound
- Industrial/Workplace Toxin
- Organic Compound
- Pollutant
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| 1-Butyl isocyanate | ChEBI | | BIC | ChEBI | | Butyl isocyanate | ChEBI | | 1-Butyl isocyanic acid | Generator | | Butyl isocyanic acid | Generator | | N-Butyl isocyanic acid | Generator | | N-Butylisocyanate | MeSH |
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| Chemical Formula | C5H9NO |
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| Average Molecular Mass | 99.131 g/mol |
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| Monoisotopic Mass | 99.068 g/mol |
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| CAS Registry Number | 111-36-4 |
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| IUPAC Name | 1-isocyanatobutane |
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| Traditional Name | butyl isocyanate |
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| SMILES | CCCCN=C=O |
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| InChI Identifier | InChI=1S/C5H9NO/c1-2-3-4-6-5-7/h2-4H2,1H3 |
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| InChI Key | HNHVTXYLRVGMHD-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as isocyanates. These are organic compounds containing the isocyanic acid tautomer, HN=C=O, of cyanic acid, HOC#N or its hydrocarbyl derivatives RN=C=O. |
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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 | Isocyanates |
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| Direct Parent | Isocyanates |
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| Alternative Parents | |
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| Substituents | - Isocyanate
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- 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 | -75°C | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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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 | 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 | Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes 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: 360 mg/kg (Oral, Rat) (2)
LD50: 1 mg/kg (Intravenous, Mouse) (1)
LC50: 0.5 mg/L over 1 hours (Inhalation, Rat) (2) |
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| Lethal Dose | 200 to 300 milligrams for an adult human (cyanide salts). (3) |
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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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| 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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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Not Available |
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| Chemspider ID | Not Available |
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| ChEBI ID | 136519 |
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| PubChem Compound ID | 8110 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | |
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