| Record Information |
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| Version | 1.0 |
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| Creation Date | 2009-04-04 05:03:21 UTC |
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| Update Date | 2016-11-09 01:08:20 UTC |
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| Accession Number | CHEM000692 |
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| Identification |
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| Common Name | Trimethylsilyl cyanide |
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| Class | Small Molecule |
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| Description | Trimethylsilyl cyanide is a chemical compound of cyanide. It is used in organic synthesis. (4) |
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| Contaminant Sources | |
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| Contaminant Type | - Cyanide Compound
- Industrial/Workplace Toxin
- Nitrile
- Organic Compound
- Organometallic
- Pollutant
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | |
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| Chemical Formula | C4H9NSi |
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| Average Molecular Mass | 99.207 g/mol |
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| Monoisotopic Mass | 99.050 g/mol |
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| CAS Registry Number | 7677-24-9 |
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| IUPAC Name | trimethylsilanecarbonitrile |
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| Traditional Name | trimethylsilyl cyanide |
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| SMILES | C[Si](C)(C)C#N |
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| InChI Identifier | InChI=1S/C4H9NSi/c1-6(2,3)4-5/h1-3H3 |
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| InChI Key | LEIMLDGFXIOXMT-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as trialkylsilanes. These are organosilicon compounds containing exactly one alkyl chain attached to the silicon atom. |
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| Kingdom | Organic compounds |
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| Super Class | Organometallic compounds |
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| Class | Organometalloid compounds |
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| Sub Class | Organosilicon compounds |
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| Direct Parent | Trialkylsilanes |
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| Alternative Parents | |
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| Substituents | - Trialkylsilane
- Organic metalloid salt
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organic salt
- Organonitrogen compound
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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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 | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 8°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 | Inhalation (2) ; oral (2) ; dermal (2) |
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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. (3) |
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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. (2) |
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| Toxicity Values | Not Available |
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| Lethal Dose | 200 to 300 milligrams for an adult human (cyanide salts). (1) |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Trimethylsilyl cyanide is used in organic synthesis. (4) |
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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. (2, 3) |
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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. (2, 3) |
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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. (3) |
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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 | Trimethylsilyl cyanide |
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| Chemspider ID | Not Available |
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| ChEBI ID | Not Available |
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| PubChem Compound ID | 82115 |
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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 | Not Available |
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