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MedKoo Cat#: 540015 | Name: Amitraz
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Amitraz, also known as Mitaban and Taktic, is an alpha-adrenergic receptor agonist and MAO inhibitor used as an insecticide in prevention of flea and tick infections. It prevents prostaglandin synthesis and may inhibit beta-cell insulin release.

Chemical Structure

Amitraz
Amitraz
CAS#33089-61-1

Theoretical Analysis

MedKoo Cat#: 540015

Name: Amitraz

CAS#: 33089-61-1

Chemical Formula: C19H23N3

Exact Mass: 293.1892

Molecular Weight: 293.41

Elemental Analysis: C, 77.78; H, 7.90; N, 14.32

Price and Availability

Size Price Availability Quantity
250mg USD 250.00 2 Weeks
1g USD 550.00 2 Weeks
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Related CAS #
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Synonym
Amitraz; Mitaban; Taktic; Ovasyn; U 36059; U-36059; U36059; NSC 324552; NSC324552; NSC-324552
IUPAC/Chemical Name
(E)-N'-(2,4-dimethylphenyl)-N-((E)-((2,4-dimethylphenyl)imino)methyl)-N-methylformimidamide
InChi Key
GUUIRIMAQGOLHT-UHFFFAOYSA-N
InChi Code
InChI=1S/C30H27BrN4O2/c31-24-10-8-22(9-11-24)17-35-21-32-16-25(35)18-33-19-28(27-7-3-5-23-4-1-2-6-26(23)27)29(20-33)30(36)34-12-14-37-15-13-34/h1-11,16,19-21H,12-15,17-18H2
SMILES Code
O=C(N1CCOCC1)C2=CN(C=C2C3=C4C=CC=CC4=CC=C3)CC5=CN=CN5CC6=CC=C(C=C6)Br
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 293.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: del Pino J, Moyano-Cires PV, Anadon MJ, Díaz MJ, Lobo M, Capo MA, Frejo MT. Molecular mechanisms of amitraz mammalian toxicity: a comprehensive review of existing data. Chem Res Toxicol. 2015 Jun 15;28(6):1073-94. doi: 10.1021/tx500534x. Epub 2015 May 26. Review. PubMed PMID: 25973576. 2: Hepperle J, Mack D, Sigalov I, Schüler S, Anastassiades M. Analysis of "Amitraz (sum)" in pears with incurred residues - Comparison of the approach covering the individual metabolites via LC-MS/MS with the approach involving cleavage to 2,4-dimethylaniline. Food Chem. 2015 Jan 1;166:240-7. doi: 10.1016/j.foodchem.2014.06.003. Epub 2014 Jun 11. PubMed PMID: 25053051. 3: Dhooria S, Agarwal R. Amitraz, an underrecognized poison: A systematic review. Indian J Med Res. 2016 Sep;144(3):348-358. doi: 10.4103/0971-5916.198723. Review. PubMed PMID: 28139533; PubMed Central PMCID: PMC5320840. 4: Del Pino J, Frejo MT, Baselga MJ, Moyano P, Díaz MJ. Impaired glutamatergic and GABAergic transmission by amitraz in primary hippocampal cells. Neurotoxicol Teratol. 2015 Jul-Aug;50:82-7. doi: 10.1016/j.ntt.2015.06.007. Epub 2015 Jun 30. PubMed PMID: 26141220. 5: Baron S, van der Merwe NA, Madder M, Maritz-Olivier C. SNP Analysis Infers that Recombination Is Involved in the Evolution of Amitraz Resistance in Rhipicephalus microplus. PLoS One. 2015 Jul 9;10(7):e0131341. doi: 10.1371/journal.pone.0131341. eCollection 2015. PubMed PMID: 26158272; PubMed Central PMCID: PMC4497657. 6: Pekmezci D, Pekmezci GZ, Guzel M, Cenesiz S, Gurler AT, Gokalp G. Efficacy of amitraz plus inactivated parapoxvirus ovis in the treatment of canine generalised demodicosis. Vet Rec. 2014 May 31;174(22):556. doi: 10.1136/vr.102226. Epub 2014 Apr 25. PubMed PMID: 24771532. 7: Muyobela J, Nkunika PO, Mwase ET. Resistance status of ticks (Acari; Ixodidae) to amitraz and cypermethrin acaricides in Isoka District, Zambia. Trop Anim Health Prod. 2015 Dec;47(8):1599-605. doi: 10.1007/s11250-015-0906-4. Epub 2015 Aug 27. PubMed PMID: 26310511. 8: Dhooria S, Behera D, Agarwal R. Amitraz: a mimicker of organophosphate poisoning. BMJ Case Rep. 2015 Oct 1;2015. pii: bcr2015210296. doi: 10.1136/bcr-2015-210296. PubMed PMID: 26430228. 9: Singh NK, Gelot IS, Jyoti, Singh V, Rath SS. Detection of amitraz resistance in Rhipicephalus (Boophilus) microplus from North Gujarat, India. J Parasit Dis. 2015 Mar;39(1):49-52. doi: 10.1007/s12639-013-0280-y. Epub 2013 Mar 15. PubMed PMID: 25698859; PubMed Central PMCID: PMC4328010. 10: Corley SW, Jonsson NN, Piper EK, Cutullé C, Stear MJ, Seddon JM. Mutation in the RmβAOR gene is associated with amitraz resistance in the cattle tick Rhipicephalus microplus. Proc Natl Acad Sci U S A. 2013 Oct 15;110(42):16772-7. doi: 10.1073/pnas.1309072110. Epub 2013 Sep 30. PubMed PMID: 24082133; PubMed Central PMCID: PMC3801038. 11: Murigu MM, Nana P, Waruiru RM, Nga'nga' CJ, Ekesi S, Maniania NK. Laboratory and field evaluation of entomopathogenic fungi for the control of amitraz-resistant and susceptible strains of Rhipicephalus decoloratus. Vet Parasitol. 2016 Jul 30;225:12-8. doi: 10.1016/j.vetpar.2016.05.026. Epub 2016 May 24. PubMed PMID: 27369570. 12: Radakovic M, Stevanovic J, Djelic N, Lakic N, Knezevic-Vukcevic J, Vukovic-Gacic B, Stanimirovic Z. Evaluation of the DNA damaging effects of amitraz on human lymphocytes in the Comet assay. J Biosci. 2013 Mar;38(1):53-62. PubMed PMID: 23385813. 13: Maciel WG, Lopes WD, Cruz BC, Gomes LV, Teixeira WF, Buzzulini C, Bichuette MA, Campos GP, Felippelli G, Soares VE, de Oliveira GP, da Costa AJ. Ten years later: Evaluation of the effectiveness of 12.5% amitraz against a field population of Rhipicephalus (Boophilus) microplus using field studies, artificial infestation (Stall tests) and adult immersion tests. Vet Parasitol. 2015 Dec 15;214(3-4):233-41. doi: 10.1016/j.vetpar.2015.10.024. Epub 2015 Nov 7. PubMed PMID: 26559460. 14: Del Pino J, Martínez MA, Castellano V, Ramos E, Martínez-Larrañaga MR, Anadón A. Effects of exposure to amitraz on noradrenaline, serotonin and dopamine levels in brain regions of 30 and 60 days old male rats. Toxicology. 2013 Jun 7;308:88-95. doi: 10.1016/j.tox.2013.03.007. Epub 2013 Mar 26. PubMed PMID: 23541472. 15: Cutullé C, Lovis L, D'Agostino BI, Balbiani GG, Morici G, Citroni D, Reggi J, Caracostantogolo JL. In vitro diagnosis of the first case of amitraz resistance in Rhipicephalus microplus in Santo Tomé (Corrientes), Argentina. Vet Parasitol. 2013 Feb 18;192(1-3):296-300. doi: 10.1016/j.vetpar.2012.10.014. Epub 2012 Oct 23. PubMed PMID: 23153823. 16: Varma PV, Bhatt S, Bhat RY. Amitraz poisoning. Indian J Pediatr. 2013 Apr;80(4):349-50. doi: 10.1007/s12098-012-0772-2. Epub 2012 May 11. PubMed PMID: 22576295. 17: Singh NK, Nandi A, Jyoti, Rath SS. Detection of amitraz resistance in Rhipicephalus (Boophilus) microplus from SBS Nagar, Punjab, India. ScientificWorldJournal. 2014 Feb 11;2014:594398. doi: 10.1155/2014/594398. eCollection 2014. PubMed PMID: 24683347; PubMed Central PMCID: PMC3934582. 18: Guo H, Zhang P, Wang J, Zheng J. Determination of amitraz and its metabolites in whole blood using solid-phase extraction and liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Mar 1;951-952:89-95. doi: 10.1016/j.jchromb.2014.01.027. Epub 2014 Jan 28. PubMed PMID: 24508680. 19: Lee S, Kim TH, Shin YW, Jeon Y, Kim J. Amitraz. Acta Crystallogr Sect E Struct Rep Online. 2013 Jul 24;69(Pt 8):o1300. doi: 10.1107/S1600536813019764. eCollection 2013. PubMed PMID: 24109378; PubMed Central PMCID: PMC3793791. 20: Papaefthimiou C, Papachristoforou A, Theophilidis G. Biphasic responses of the honeybee heart to nanomolar concentrations of amitraz. Pestic Biochem Physiol. 2013 Sep;107(1):132-7. doi: 10.1016/j.pestbp.2013.06.005. Epub 2013 Jun 18. PubMed PMID: 25149247.