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Amitraz (BTS-27419) Sale

(Synonyms: 双甲脒; BTS-27419) 目录号 : GC33983

A formamidine acaricide

Amitraz (BTS-27419) Chemical Structure

Cas No.:33089-61-1

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10mM (in 1mL DMSO)
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100mg
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产品描述

Amitraz is a formamidine acaricide.1 It induces mortality and reduces fecundity in adult R. annulatus when used at a concentration of 300 ppm. It is lethal to adult H. bipinosa (LC50 = 181 ppm). Amitraz (100 ?M) reduces viability of primary rat hippocampal cells.2 In vivo, amitraz (170 mg/kg) increases malondialdehyde (MDA) and nitric oxide (NO) levels and decreases superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPX) activities in rat liver, kidney, brain, spleen, and testis.3 Dietary administration of amitraz reduces larval weight and larval and pupal survival in honey bee (A. mellifera) populations.4

1.Ravindran, R., Jyothimol, G., Amithamol, K.K., et al.In vitro efficacy of amitraz, coumaphos, deltamethrin and lindane against engorged female Rhipicephalus (Boophilus) annulatus and Haemaphysalis bispinosa ticksExp. Appl. Acarol.75(2)241-253(2018) 2.Del Pino, J., Frejo, M.T., Baselga, M.J.A., et al.Impaired glutamatergic and GABAergic transmission by amitraz in primary hippocampal cellsNeurotoxicol. Teratol.5082-87(2015) 3.Kanbur, M., Sili?, Y., Eraslan, G., et al.The toxic effect of cypermethrin, amitraz and combinations of cypermethrin-amitraz in ratsEnviron. Sci. Pollut. Res. Int.23(6)5232-5242(2016) 4.Dai, P., Jack, C.J., Mortensen, A.N., et al.Chronic toxicity of amitraz, coumaphos and fuvalinate to Apis mellifera L. larvae reared in vitroSci. Rep.8(1)5635(2018)

Chemical Properties

Cas No. 33089-61-1 SDF
别名 双甲脒; BTS-27419
Canonical SMILES CN(/C=N/C1=CC=C(C)C=C1C)/C=N/C2=CC=C(C)C=C2C
分子式 C19H23N3 分子量 293.41
溶解度 DMSO : 50 mg/mL (170.41 mM);Water : < 0.1 mg/mL (insoluble) 储存条件 Store at -20°C
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1 mM 3.4082 mL 17.041 mL 34.082 mL
5 mM 0.6816 mL 3.4082 mL 6.8164 mL
10 mM 0.3408 mL 1.7041 mL 3.4082 mL
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Research Update

Effects of the pesticide Amitraz and its metabolite BTS 27271 on insulin and glucagon secretion from the perfused rat pancreas: involvement of alpha2D-adrenergic receptors

Metabolism 1999 Nov;48(11):1461-9.PMID:10582558DOI:10.1016/s0026-0495(99)90160-9.

The study purpose was to investigate the direct effect of Amitraz, a formamidine insecticide/acaricide, and its active metabolite BTS 27271 on insulin and glucagon secretion from the perfused rat pancreas. Amitraz and BTS 27271 (0.01, 0.1, 1, and 10 micromol/L) inhibited insulin secretion in a concentration-dependent manner. Amitraz increased glucagon secretion at 10 micromol/L, whereas BTS 27271 increased glucagon secretion at 1 and 10 micromol/L. Amitraz- and BTS 27271-induced decreases in insulin secretion and increases in glucagon secretion were not abolished during the 10-minute washout period. During the arginine treatment, both Amitraz and BTS 27271 groups (0.1, 1, and 10 micromol/L) had lower insulin secretion and higher glucagon secretion than the control group. Idazoxan, an alpha2A/2D-adrenergic receptor (AR) antagonist, prevented the inhibitory effect of Amitraz on insulin secretion in a concentration-dependent manner, but prazosin, an alpha1- and alpha2B/2C-AR antagonist, failed to antagonize the effect of Amitraz. These results demonstrate that (1) Amitraz and BTS 27271 inhibit insulin and stimulate glucagon secretion from the perfused rat pancreas, (2) Amitraz inhibits insulin secretion by activation of alpha2D-ARs, since rats have alpha2D- but not alpha2A-ARs, and (3) Amitraz and BTS 27271 may have a high binding affinity to the alpha2D-ARs of pancreatic islets.

Amitraz poisoning

Indian J Pediatr 2013 Apr;80(4):349-50.PMID:22576295DOI:10.1007/s12098-012-0772-2.

Amitraz is a formamidine insecticide and acaricide which acts on alpha 2-adrenergic receptors. There is little information available in the literature about the toxicity and treatment of poisoning by this compound. The authors report Amitraz poisoning in a 13-y-old boy which was managed with supportive care with a good outcome.

Poisoning with Amitraz

Toxicol Rev 2003;22(2):71-4.PMID:15071816DOI:10.2165/00139709-200322020-00001.

Amitraz, an insecticide and veterinary medicine, has been available in many countries since 1974 but reports of poisoning with it have only become prominent in the last 7 years. The vast majority of cases have occurred in Turkey and have involved children. The data available, both human and animal, do not allow clear separation of the features of toxicity of Amitraz from those of the hydrocarbon solvents in which it is commonly dissolved. Amitraz stimulates alpha 2-adrenoceptors resulting in impairment of consciousness, respiratory depression, convulsions, bradycardia, hypotension, hypothermia and hypoglycaemia. Even the most severely poisoned patients recover with nothing more than intensive care; only one possible death has been documented. Animal studies indicate that the alpha 2-adrenoceptor antagonists, yohimbine and atipamezole, can reverse amitraz-induced toxicity but they have not been assessed in poisoned humans.

Oxidative stress and cell death induction by Amitraz and its metabolite BTS-27271 mediated through cytochrome P450 and NRF2 pathway alteration in primary hippocampal cell

Food Chem Toxicol 2019 Jul;129:87-96.PMID:31029719DOI:10.1016/j.fct.2019.04.042.

Amitraz is a neurotoxic formamidine pesticide that induces cell death in hippocampal neurons, although its mechanisms are unknown. Amitraz produces reactive oxygen species (ROS), which could lead to cell death. Amitraz was shown to induce different cytochrome P450 (CYP) isoenzymes involved with ROS and apoptotic cell death induction. Finally, Amitraz was described to decrease the activity of antioxidant enzymes regulated through KEAP1/NRF2 pathway, thus likely leading to a reduction of ROS elimination and to cell death induction. We evaluated the effect of Amitraz or BTS-27271 co-treatment with or without the antioxidant N-acetylcysteine and/or the unspecific CYP inhibitor 1-aminobenzotriazole on cell viability and its related mechanisms in wild type and silenced primary hippocampal neurons after 24 h treatment. We observed that Amitraz produced oxidative stress and CYPs induction leading to apoptotic cell death. ROS generation was partially mediated by CYPs induction and downregulation of NRF2-pathway through KEAP1 overexpression. These data could help explain the mechanism by which Amitraz induces cell death and oxidative stress and provide a therapeutic strategy to protect against this effect in case of poisoning.

Amitraz, an underrecognized poison: A systematic review

Indian J Med Res 2016 Sep;144(3):348-358.PMID:28139533DOI:10.4103/0971-5916.198723.

Background & objectives: Amitraz is a member of formamidine family of pesticides. Poisoning from Amitraz is underrecognized even in areas where it is widely available. It is frequently misdiagnosed as organophosphate poisoning. This systematic review provides information on the epidemiology, toxicokinetics, mechanisms of toxicity, clinical features, diagnosis and management of Amitraz poisoning. Methods: Medline and Embase databases were searched systematically (since inception to January 2014) for case reports, case series and original articles using the following search terms: 'Amitraz', 'poisoning', 'toxicity', 'intoxication' and 'overdose'. Articles published in a language other than English, abstracts and those not providing sufficient clinical information were excluded. Results: The original search yielded 239 articles, of which 52 articles described human cases. After following the inclusion and exclusion criteria, 32 studies describing 310 cases (151 females, 175 children) of human poisoning with Amitraz were included in this systematic review. The most commonly reported clinical features of Amitraz poisoning were altered sensorium, miosis, hyperglycaemia, bradycardia, vomiting, respiratory failure, hypotension and hypothermia. Amitraz poisoning carried a good prognosis with only six reported deaths (case fatality rate, 1.9%). Nearly 20 and 11.9 per cent of the patients required mechanical ventilation and inotropic support, respectively. The role of decontamination methods, namely, gastric lavage and activated charcoal was unclear. Interpretation & conclusions: Our review shows that Amitraz is an important agent for accidental or suicidal poisoning in both adults and children. It has a good prognosis with supportive management.