Record Information |
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Version | 2.0 |
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Creation Date | 2009-06-18 21:54:33 UTC |
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Update Date | 2014-12-24 20:23:06 UTC |
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Accession Number | T3D1076 |
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Identification |
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Common Name | Methyl (5Z)-3-amino-5-(nitromethylidene)dithiole-4-carboxylate |
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Class | Small Molecule |
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Description | Aromatic heterocycle containing a nitromethylene substituent. Fast acting neurotoxicant, effective both by contact or oral ingestion; they are relatively safe to vertebrates and degrade rapidly in the environment. (1) |
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Compound Type | - Amide
- Amine
- Ester
- Ether
- Nitromethylene
- Organic Compound
- Pesticide
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | Methyl (3Z)-5-amino-3-(nitromethylene)-3H-1,2-dithiole-4-carboxylate |
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Chemical Formula | C6H6N2O4S2 |
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Average Molecular Mass | 234.253 g/mol |
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Monoisotopic Mass | 233.977 g/mol |
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CAS Registry Number | 78649-93-1 |
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IUPAC Name | methyl 5-amino-3-(nitromethylidene)-3H-1,2-dithiole-4-carboxylate |
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Traditional Name | methyl 3-amino-5-(nitromethylidene)-1,2-dithiole-4-carboxylate |
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SMILES | COC(=O)C1=C(N)SSC1=C[N+]([O-])=O |
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InChI Identifier | InChI=1S/C6H6N2O4S2/c1-12-6(9)4-3(2-8(10)11)13-14-5(4)7/h2H,7H2,1H3/b3-2- |
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InChI Key | InChIKey=IAWCIGLAQKOOTG-IHWYPQMZSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as vinylogous amides. These are organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Vinylogous amides |
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Sub Class | Not Available |
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Direct Parent | Vinylogous amides |
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Alternative Parents | |
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Substituents | - Methyl ester
- 1,2-dithiole
- Dithiole
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Vinylogous amide
- Carboxylic acid ester
- Ketene acetal or derivatives
- C-nitro compound
- Organic disulfide
- Organic nitro compound
- Organoheterocyclic compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Allyl-type 1,3-dipolar organic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxoazanium
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organic nitrogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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 | Not Available | Boiling Point | Not Available | Solubility | Not Available | 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 LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0290000000-5c5615890d1e429b865f | 2019-02-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-007c-5920000000-9f3a8fe660c3b4fc61f6 | 2019-02-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kf-9100000000-c27c4a830c86e3289744 | 2019-02-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00lr-0690000000-5abe13003b02d37c148a | 2019-02-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-2930000000-dea1f7f36093a21e9275 | 2019-02-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-02t9-2910000000-fccdf9d8c9ff31b00552 | 2019-02-23 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Dermal (1); Oral (1). |
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Mechanism of Toxicity | Acts as a neurotransmitter mimic , having both excitatory and depressant effects, eventually blocking postsynaptic nicotinic receptors. (1) |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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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 | Nitromethylenes are used as pesticides. (1) |
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Minimum Risk Level | Not Available |
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Health Effects | Nitromethylenes are neurotoxic. (1) |
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Symptoms | Not Available |
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Treatment | Not Available |
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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 | 5479865 |
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ChEMBL ID | Not Available |
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ChemSpider ID | 4586506 |
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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 | Not Available |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Methyl (5Z)-3-amino-5-(nitromethylidene)dithiole-4-carboxylate |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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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 | Not Available |
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General References | - Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
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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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