Amitraz
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Basic Info
| Common Name | Amitraz(F05680) |
| 2D Structure | |
| FRCD ID | F05680 |
| CAS Number | 33089-61-1 |
| PubChem CID | 36324 |
| Formula | C19H23N3 |
| IUPAC Name | N'-(2,4-dimethylphenyl)-N-[(2,4-dimethylphenyl)iminomethyl]-N-methylmethanimidamide |
| InChI Key | QXAITBQSYVNQDR-UHFFFAOYSA-N |
| InChI | 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 |
| Canonical SMILES | CC1=CC(=C(C=C1)N=CN(C)C=NC2=C(C=C(C=C2)C)C)C |
| Isomeric SMILES | CC1=CC(=C(C=C1)N=CN(C)C=NC2=C(C=C(C=C2)C)C)C |
| Synonyms |
Triazid
BAAM
AMITRAZ
33089-61-1
Mitac
Taktic
Azaform
Mitaban
Acarac
Azadieno
|
| Classifies |
Illegal Additives
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Xylenes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | m-Xylenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| 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 |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 293.414 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 4 |
| Complexity | 354 |
| Monoisotopic Mass | 293.189 |
| Exact Mass | 293.189 |
| XLogP | 5.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8995 |
| Human Intestinal Absorption | HIA+ | 0.7645 |
| Caco-2 Permeability | Caco2+ | 0.7328 |
| P-glycoprotein Substrate | Non-substrate | 0.7867 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6648 |
| Non-inhibitor | 0.6497 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.5691 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7465 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6259 |
| CYP450 2D6 Substrate | Non-substrate | 0.7055 |
| CYP450 3A4 Substrate | Non-substrate | 0.5134 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5242 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7996 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.5735 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5505 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8974 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9705 |
| Non-inhibitor | 0.7973 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Carcinogens | 0.6526 |
| Fish Toxicity | High FHMT | 0.8057 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8939 |
| Honey Bee Toxicity | Low HBT | 0.8350 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | II | 0.7578 |
| Carcinogenicity (Three-class) | Warning | 0.4488 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -5.4073 | LogS |
| Caco-2 Permeability | 1.6879 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.8358 | LD50, mol/kg |
| Fish Toxicity | 1.2096 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.3948 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Yam | Japan | 0.05ppm | |||
| Onion | Japan | 0.05ppm | |||
| Aril spices | 0870000 | European Union | 0.1* | 26/04/2017 | |
| Other Terrestrial Mammals,Edible Offal | Japan | 0.2ppm | |||
| Pig,Edible Offal | Japan | 0.2ppm | |||
| Cattle,Edible Offal | Japan | 0.2ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.2ppm | |||
| Pig,Kidney | Japan | 0.2ppm | |||
| Cattle,Kidney | Japan | 0.2ppm | |||
| Other Terrestrial Mammals,Liver | Japan | 0.2ppm | |||
| Pig,Liver | Japan | 0.2ppm | |||
| Cattle,Liver | Japan | 0.2ppm | |||
| Other Terrestrial Mammals,Fat | Japan | 0.4ppm | |||
| Pig,Fat | Japan | 0.1ppm | |||
| Cattle,Fat | Japan | 0.1ppm | |||
| Other Terrestrial Mammals,Muscle | Japan | 0.1ppm | |||
| Pig,Muscle | Japan | 0.05ppm | |||
| Cattle,Muscle | Japan | 0.05ppm | |||
| Other Herbs | Japan | 0.05ppm | |||
| Other Spices | Japan | 0.5ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Chemical tick control practices in southwestern and northwestern Uganda. | Ticks Tick Borne Dis | 2018 May | 29606621 |
| Acaricide, fungicide and drug interactions in honey bees (Apis mellifera). | PLoS One | 2013 | 23382869 |
| Laboratory evaluation of verbutin as a synergist of acaricides against larvae of Rhipicephalus (Boophilus) microplus (Acari: Ixodidae). | J Econ Entomol | 2010 Aug | 20857748 |
| Desorption electrospray ionization mass spectrometry for trace analysis of agrochemicals in food. | Anal Chem | 2009 Jan 15 | 19090743 |
| Evaluation of developmental toxicity of amitraz in Sprague-Dawley rats. | Arch Environ Contam Toxicol | 2007 Jan | 17083001 |
Targets
- General Function:
- Thioesterase binding
- Specific Function:
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol.
- Gene Name:
- ADRA2A
- Uniprot ID:
- P08913
- Molecular Weight:
- 48956.275 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase.
- Gene Name:
- HTR7
- Uniprot ID:
- P34969
- Molecular Weight:
- 53554.43 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Cytokine activity
- Specific Function:
- Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells.
- Gene Name:
- IL1A
- Uniprot ID:
- P01583
- Molecular Weight:
- 30606.29 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Vitamin d 24-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
- Gene Name:
- CYP1A1
- Uniprot ID:
- P04798
- Molecular Weight:
- 58164.815 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]