U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H23N3
Molecular Weight 293.406
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of AMITRAZ

SMILES

CN(\C=N\C1=CC=C(C)C=C1C)\C=N\C2=CC=C(C)C=C2C

InChI

InChIKey=QXAITBQSYVNQDR-ZIOPAAQOSA-N
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+

HIDE SMILES / InChI

Molecular Formula C19H23N3
Molecular Weight 293.406
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://www.merckvetmanual.com/mvm/pharmacology/ectoparasiticides/ectoparasiticides_used_in_large_animals.html

Amitraz (development code BTS27419) is a non-systemic acaricide and insecticide and has also been described as a scabicide. It was first synthesized by the Boots Co. in England in 1969. Amitraz is the only formamidine used as an ectoparasiticide. It appears to act by inhibition of the enzyme monoamine oxidase and as an agonist at octopamine receptors. Monoamine oxidase metabolizes amine neurotransmitters in ticks and mites, and octopamine is thought to modify tonic contractions in parasite muscles. Amitraz has a relatively wide safety margin in mammals; the most frequently associated adverse effect is sedation, which may be associated with an agonist activity of amitraz on α2-receptors in mammalian species. Amitraz is available as a spray or dip for use against mites, lice, and ticks in domestic livestock. It controls lice and mange in pigs and psoroptic mange in sheep. In cattle, it has been used in dips, sprays, or pour-ons for control of single-host and multihost tick species. In dipping baths, amitraz can be stabilized by the addition of calcium hydroxide and maintained by standard replenishment methods for routine tick control. An alternative method involves the use of total replenishment formulations in which the dip bath is replenished with full concentration of amitraz at weekly intervals before use. Amitraz is contraindicated in horses. Amitraz has antipyretic and antiinflammatory activity in vivo, and also has been shown to inhibit prostaglandin E2 synthesis(13). Decreased body temperature was observed in two of our cases. The basic approach to the patient with amitraz poisoning includes initial stabilization, treatment to reduce absorption and measures to improve elimination of the toxin. The medical management is essentially symptomatic and supportive. There is no specific antidote. Despite life-threatening symptomatology, all cases may recover completely. In this study we would like to emphasize that the incidence of poisoning with amitraz is increasing due to its widespread use in veterinary medicine. In order to minimize amitraz poisoning, public education should be given on primary prevention of poisoning and besides, producers should redesign containers as childproof packagers with warning labels

CNS Activity

Curator's Comment: CNS depression was the most common clinical sign (76.8%) of amitraz poisoning

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Development and validation of an analytical method for total amitraz in fruit and honey with quantification by gas chromatography-mass spectrometry.
2007-03
Field evaluation of a botanical natural product against the pear psylla (Homoptera: Psyllidae).
2007-02
Identification of pesticide transformation products in food by liquid chromatography/time-of-flight mass spectrometry via "fragmentation-degradation" relationships.
2007-01-01
Flawed ethics recommendations of the U.S. EPA's human studies review board.
2007-01
Evaluation of developmental toxicity of amitraz in Sprague-Dawley rats.
2007-01
Neurotoxic and general effects of combined subchronic exposure of rats to insecticides and heavy metals.
2006-12
Electrochemical monitoring of the biodegradation of 2,4-dimethylaniline.
2006-11-15
Elimination of sarcoptic mange due to Sarcoptes scabiei var suis from a 1800-sow farrow-to-finish farm.
2006-10-28
Electrochemical investigation of the effect of pH and solvent on amitraz stability.
2006-10-18
Acute amitraz intoxication: retrospective analysis of 45 cases.
2006-10
Efficacy of several anti-tick treatments to prevent the transmission of Rickettsia conorii under natural conditions.
2006-10
Canine renal cortical necrosis and haemorrhage following ingestion of an Amitraz-formulated insecticide dip.
2006-09
Prevalence and potential risk factors for amitraz resistance in Boophilus microplus ticks in cattle farms in the State of Yucatan, Mexico.
2006-08-17
Demodicosis in nine prairie dogs (Cynomys ludovicianus).
2006-08
[Compatibility of two fungal biocontrol agents conidia with commercial chemical acaricides].
2006-07
Multimodal approach to treatment for control of fur mites.
2006-07
The use of a pour-on and spray dip containing Amitraz to control ticks (Acari: Ixodidae) on cattle.
2006-06
Suspected drug-induced destructive cholangitis in a young dog.
2006-06
Pesticide exposure: the hormonal function of the female reproductive system disrupted?
2006-05-31
[A case of very serious Sarcoptes mange in alpacas (Lama pacos)].
2006-04-15
In vitro tests for evaluation of the hatchability of the eggs of Psoroptes mites following exposure to acaricidal compounds.
2006-03
Comparative tick counts on game, cattle and sheep on a working game ranch in Kenya.
2006-01
Update on canine demodicosis.
2006-01
Acute amitraz poisoning in adults: clinical features, laboratory findings, and management.
2006
Determination of acaricide residues in saudi arabian honey and beeswax using solid phase extraction and gas chromatography.
2006
Acaricide efficiency of amitraz/cypermethrin and abamectin pour-on preparations in game.
2005-12
Modification of MTT assay conditions to examine the cytotoxic effects of amitraz on the human lymphoblastoid cell line, WIL2NS.
2005-12
Effects of the insecticide amitraz, an alpha2-adrenergic receptor agonist, on human luteinized granulosa cells.
2005-11
Amitraz: an unusual aetiology of Ogilvie's syndrome.
2005-09
Near-fatal amitraz intoxication: the overlooked pesticide.
2005-09
[Alcoholic extract of lemongrass (Cymbopogon citratus) on the control of Boophilus microplus in cattle].
2005-08-26
Diagnosis of amitraz resistance in Boophilus microplus in New Caledonia with the modified Larval Packet Test.
2005-06-30
BmiGI: a database of cDNAs expressed in Boophilus microplus, the tropical/southern cattle tick.
2005-06
[Additional information on the article amitraz intoxications in the horse].
2005-05-01
Comparative acaricide susceptibility and detoxifying enzyme activities in field-collected resistant and susceptible strains of Tetranychus urticae.
2005-05
[In Vitro efficacy of comercial formulations of ixocidides in engorged female of Boophilus microplus collected of dairy cattle at Paraíba Valey in the state of São Paulo].
2005-03-21
Comparison of in vitro and in vivo ectoparasiticide activity of experimental benzimidazole-carbamate with permethrin and amitraz.
2005-03
Efficacy of a collar impregnated with amitraz and pyriproxyfen for prevention of experimental tick infestations by Rhipicephalus sanguineus, Ixodes ricinus, and Ixodes scapularis in dogs.
2005-01-15
Mode of inheritance of amitraz resistance in a Brazilian strain of the southern cattle tick, Boophilus microplus (Acari: Ixodidae).
2005
The relationship between surface adsorption and the hydrolysis of amitraz in anionic surfactant solutions.
2005
Intravenous amitraz poisoning.
2005
Susceptibility of Amblyomma variegatum ticks to acaricides in Ghana.
2005
Structural characterization, physicochemical properties, suspension stability, and adsorption properties of four solid forms of amitraz.
2004-12-01
What is your diagnosis? Juvenile-onset generalised demodicosis.
2004-11
Effects of amitraz on cytochrome P450-dependent monooxygenases and estrogenic activity in MCF-7 human breast cancer cells and immature female rats.
2004-11
Factors that influence the prevalence of acaricide resistance and tick-borne diseases.
2004-10-28
Development of a method for the detection and confirmation of the alpha-2 agonist amitraz and its major metabolite in horse urine.
2004-10
A comparative analysis of immunorestoration and recovery with conventional and immunotherapeutic protocols in canine generalized demodicosis: a newer insight of immunotherapeutic efficacy of T11TS.
2004
Rapid quantitative assay for acaricidal effects on Sarcoptes scabiei var. suis and Otodectes cynotis.
2004
Octopaminergic agonists for the cockroach neuronal octopamine receptor.
2003
Patents

Sample Use Guides

For Use In Animals Only: topically treated with MITABAN (amitraz) at a rate of 10.6 milliliters (contents of one bottle) per 2 gallons of warm water (250 ppm active drug).
Route of Administration: Topical
In Vitro Use Guide
The toxicity of the acaricide amitraz and its effect on foot-and-mouth disease virus multiplication were evaluated in IB-RS-2 cells in vitro. Foot-and-mouth disease virus infectivity remained essentially unchanged in cells exposed to amitraz (20 ug/ml) 24 hr prior to virus infection or after the adsorption period. Viral RNA synthesis evaluated through [3H]uridine incorporation in cells treated for 24 hr prior to infection was not affected by amitraz
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:34:28 GMT 2025
Edited
by admin
on Wed Apr 02 08:34:28 GMT 2025
Record UNII
33IAH5017S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMITRAZ
GREEN BOOK   HSDB   INN   MART.   MI   USAN   USP   USP-RS  
INN   USAN  
Official Name English
CERTIFECT
Preferred Name English
U-36,059
Code English
AMITRAZ [USP-RS]
Common Name English
PROMERIS DUO COMPONENT AMITRAZ
Brand Name English
AMITRAZ [EMA EPAR VETERINARY]
Common Name English
U-36-059
Code English
amitraz [INN]
Common Name English
U-36059
Code English
AMITRAZ [GREEN BOOK]
Common Name English
AMITRAZ [MART.]
Common Name English
AMITRAZ [MI]
Common Name English
METHANIMIDAMIDE, N'-(2,4-DIMETHYLPHENYL)-N-(((2,4-DIMETHYLPHENYL)IMINO)METHYL)-N-METHYL-
Systematic Name English
AMITRAZ [USP MONOGRAPH]
Common Name English
N-METHYLBIS(2,4-XYLYLIMINOMETHYL)AMINE
Systematic Name English
AMITRAZ [HSDB]
Common Name English
N-METHYL-N'-2,4-XYLYL-N-(N-2,4-XYLYLFORMIMIDOYL)FORMAMIDINE
Systematic Name English
NSC-324552
Code English
AMITRAZ [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C737
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
WHO-VATC QP53AD51
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
CFR 21 CFR 524.86
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
EPA PESTICIDE CODE 106201
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
WHO-VATC QP53AD01
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
EMA VETERINARY ASSESSMENT REPORTS PROMERIS DUO
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
Code System Code Type Description
ALANWOOD
amitraz
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
EMA VETERINARY ASSESSMENT REPORTS
CERTIFECT (AUTHORISED)
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY DOGS
NCI_THESAURUS
C74339
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
SMS_ID
100000087403
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
FDA UNII
33IAH5017S
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
ChEMBL
CHEMBL1365675
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
MESH
C014983
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
CHEBI
2665
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
EVMPD
SUB05461MIG
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
RS_ITEM_NUM
1028000
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
MERCK INDEX
m1752
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY Merck Index
PUBCHEM
36324
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
DRUG BANK
DB11373
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
CAS
33089-61-1
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
HSDB
6939
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
ECHA (EC/EINECS)
251-375-4
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
RXCUI
17763
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY RxNorm
INN
5183
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PRIMARY
EPA CompTox
DTXSID5023871
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
WIKIPEDIA
AMITRAZ
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
NSC
324552
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
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