| Record Information |
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| Version | 2.0 |
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| Creation Date | 2013-04-25 07:56:49 UTC |
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| Update Date | 2014-12-24 20:26:32 UTC |
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| Accession Number | T3D3792 |
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| Identification |
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| Common Name | Amitraz |
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| Class | Small Molecule |
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| Description | Amitraz (development code BTS27419) is a non-systemic acaricide and insecticide. Kinetics and mechanism of amitraz hydrolysis in aqueous media by HPLC and GC-MS. It was first synthesized by the Boots Co. in England in 1969. Amitraz has been found to have an insect repellent effect, works as an insecticide and also as a pesticide synergist. Its effectiveness is traced back on alpha-adrenergic agonist activity, interaction with octopamine receptors of the central nervous system and inhibition of monoamine oxidases and prostaglandin synthesis. Therefore, it leads to overexcitation and consequently paralysis and death in insects. Because amitraz is less harmful to mammals, amitraz is among many other purposes best known as insecticide against mite- or tick-infestation of dogs. |
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| Compound Type | - Amine
- Insecticide
- Organic Compound
- Pesticide
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | |
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| Chemical Formula | C19H23N3 |
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| Average Molecular Mass | 293.406 g/mol |
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| Monoisotopic Mass | 293.189 g/mol |
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| CAS Registry Number | 33089-61-1 |
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| IUPAC Name | (E)-N'-(2,4-dimethylphenyl)-N-[(1E)-[(2,4-dimethylphenyl)imino]methyl]-N-methylmethanimidamide |
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| Traditional Name | (E)-N'-(2,4-dimethylphenyl)-N-[(1E)-[(2,4-dimethylphenyl)imino]methyl]-N-methylmethanimidamide |
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| SMILES | CN(\C=N\C1=CC=C(C)C=C1C)\C=N\C1=CC=C(C)C=C1C |
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| InChI Identifier | InChI=1S/C19H23N3/c1-14-6-8-18(16(3)10-14)20-12-22(5)13-21-19-9-7-15(2)11-17(19)4/h6-13H,1-5H3/b20-12+,21-13+ |
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| InChI Key | InChIKey=QXAITBQSYVNQDR-ZIOPAAQOSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Xylenes |
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| Direct Parent | m-Xylenes |
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| Alternative Parents | |
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| Substituents | - M-xylene
- Formamidine
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboxylic acid amidine
- Amidine
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic 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 | 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 | splash10-0006-0090000000-ac81a903887ed3d30170 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0290000000-f8b82f972a8577637965 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-08i4-5950000000-200a509d3d4917675133 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0090000000-44abae5cd412b000cb9a | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0090000000-73072ce329047302ccf2 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004l-1690000000-2a29d4351ada622dea91 | 2016-08-03 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | The pharmacological activity of amitraz includes different mechanisms of action leading to toxic effects in humans as well as in animals. Many of these effects and most of the effects on humans are caused by its alpha-adrenergic agonist activity. Furthermore amitraz inhibits prostaglandin synthesis, interacts with the octopamine receptors of the central nervous system and inhibits monoamine oxidases. Animal studies revealed that damages due to amitraz poisoning can be recovered even after exposure to a potentially lethal dose. This could mean that amitraz' effects are reversible or at least are recoverable. When an amitraz poisoning is lethal, death results from respiratory depression. (Wikipedia) |
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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 | This is a man-made compound that is used as a pesticide. |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | The toxic effects to humans following on amitraz-uptake include loss of consciousness, vomiting, respiratory failure, miosis, hypothermia, bradycardia, hyperglycemia and central nervous system depression. (Wikipedia) |
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| Treatment | In case of an amitraz overdose in humans atipamezole or yohimbine, which act as α2-antagonists, can be used as antidote. Initially it is important to remove the patient from the amitraz contaminated area. When amitraz has been inhaled the patient should first get respiratory protection. Additionally the patient should be supplied with 4 L oxygen per minute. In case of an intoxication via skin-contact, contaminated clothes should be removed first. Affected areas need to be washed with water. If eyes have been exposed to amitraz, anesthesia should be administered and the eyes carefully washed. After the oral intake of amitraz it is important to make the patient drink ca. 0.3 L water to reduce amitraz´ irritating effect on the gullet. Furthermore, it is important to prevent the patient as much as possible from vomiting, to reduce the risk of further aspiration of amitraz. Subsequently, the patient need to be observed for at least 24 hours to ensure that the symptoms do not recur. (Wkipedia) |
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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 | Not Available |
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| ChEMBL ID | CHEMBL1365675 |
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| ChemSpider ID | 33405 |
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| KEGG ID | C10995 |
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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 | Not Available |
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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 | T3D3792.pdf |
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| General References | Not Available |
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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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