ContaminantDB: Amitraz

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (8)XML

Record Information

Version

1.0

Creation Date

2013-04-25 07:56:49 UTC

Update Date

2016-11-09 01:08:58 UTC

Accession Number

CHEM002753

Identification

Common Name

Amitraz

Class

Small Molecule

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.

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Insecticide
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Mitac	Kegg

Chemical Formula

C₁₉H₂₃N₃

Average Molecular Mass

293.406 g/mol

Monoisotopic Mass

293.189 g/mol

CAS Registry Number

33089-61-1

IUPAC Name

(E)-N'-(2,4-dimethylphenyl)-N-[(1E)-[(2,4-dimethylphenyl)imino]methyl]-N-methylmethanimidamide

Traditional Name

(E)-N'-(2,4-dimethylphenyl)-N-[(1E)-[(2,4-dimethylphenyl)imino]methyl]-N-methylmethanimidamide

SMILES

CN(\C=N\C1=CC=C(C)C=C1C)\C=N\C1=C(C)C=C(C)C=C1

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+

InChI Key

QXAITBQSYVNQDR-ZIOPAAQOSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Xylenes

Direct Parent

m-Xylenes

Alternative Parents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Acaricides (C10995 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00065 g/L	ALOGPS
logP	4.42	ALOGPS
logP	5.41	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	8.83	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.96 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98 m³·mol⁻¹	ChemAxon
Polarizability	35.71 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-ac81a903887ed3d30170	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0290000000-f8b82f972a8577637965	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08i4-5950000000-200a509d3d4917675133	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-44abae5cd412b000cb9a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0090000000-73072ce329047302ccf2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-1690000000-2a29d4351ada622dea91	Spectrum

Toxicity Profile

Route of Exposure

Not Available

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)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Not Available

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)

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)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Amitraz

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

C10995

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Amitraz (CHEM002753)

Structure for CHEM002753: Amitraz