Allethrin appears as a clear amber-colored viscous liquid. Insoluble and denser than water. Toxic by ingestion, inhalation, and skin absorption. A synthetic household insecticide that kills flies, mosquitoes, garden insects, etc.
AFTER ADMINISTRATION OF LABELED ALLETHRIN TO MALE RATS, THE MAJOR METABOLITES FOUND WERE ALCOHOL-ACIDS. FROM NMR AND MASS SPECTRA A THIRD METABOLITE WAS IDENTIFIED AS ALLETHRIN WITH ONE CYCLOPROPANE METHYL HYDROXYLATED AND OXIDATION OF THE TRANSMETHYL TO A CARBOXYL GROUP. ...
/IN STUDYING THE METABOLISM OF ALLETHRIN IN HOUSEFLIES, IT WAS FOUND THAT IN/ ALLETHRIN LABELED IN THE KETOCYCLOPENTENYL PORTION OF THE MOLECULE, A METABOLITE THAT BEHAVED AS KETOCYCLOPENTENOL WAS ISOLATED BY PAPER CHROMATOGRAPHY. ... INVESTIGATORS USING ALLETHRIN LABELED IN CHRYSANTHEMUMIC ACID PORTION OF MOLECULE WERE ABLE TO DETECT ONLY TRACES OF ACID IN HOUSEFLY HOMOGENATES OR EXCRETA. ... ONLY TRACES OF UNCHANGED ALLETHRIN WERE RECOVERABLE AND THE BULK OF THE RECOVERED MATERIAL MUST BE A DERIVATIVE OF THE INTACT ESTER OR OF THE ACID.
Allethrin is oxidized not only at the chrysanthemate isobutenyl moiety to the corresponding primary alcohol but also at the allyl group to 1'-hydroxyprop-2'-enyl and 2',3'-dihydroxy-propyl derivatives, or at a methyl group on the cyclopropyl moiety to a hydroxy derivative. Allethrin is also converted to chrysanthemum dicarboxylic acid and allethrolone.
When allethrin was applied topically to houseflies, chromatography indicated the presence of allethrone and chrysanthemic acid in addition to allethrin and three unidentified compounds.
Upon absorption of allethrine , biotransformation takes place through hydrolysis of the
central ester bond, oxidative attacks at several sites, and conjugation reactions to produce a complex array of primary and secondary water-soluble metabolites that undergo urinary and biliary excretion. Allethrin is oxidized not only at the chrysanthemate isobutenyl moiety to the corresponding primary alcohol but also at the allyl group to 1'-hydroxyprop-2'-enyl and 2',3'-dihydroxy-propyl derivatives, or at a methyl group on the cyclopropyl moiety to a hydroxy derivative. It is widely accepted that metabolism results in the formation of compounds that have little or no demonstrable toxicity, although the formation of reactive or toxic intermediates cannot be ruled out, and it appears that cleavage of the ester bond results in substantial detoxification. Allethrin is also converted to chrysanthemum dicarboxylic acid and allethrolone. Allethrin leaves the body quickly, mainly in the urine, but also in feces and breath. (L857, A558)
IDENTIFICATION AND USE: Allethrins is a clear to amber colored viscous liquid which is miscible with most organic solvents. It is completely soluble with chloroform, ethyl acetate, toluene and dichloromethane and it is stable under normal conditions and use. Allethrins are a mixture of isomers and the product is used as an insecticide. HUMAN EXPOSURE and TOXICITY: Despite their extensive world wide use, there are relatively few reports of human pyrethroid poisoning. In individuals exposed to pyrethroids, dermal; application to the skin has resulted in paresthesia and may be stimulated by increases in heat, sunlight, scratching, humidity, or the application of water. Pyrethroid ingestion can cause sore throat, nausea, vomiting and abdominal pain. Dizziness and fatigue are common, and palpitations, chest tightness and blurred vision have also occurred. Contact allergy to pyrethroids has also been noted. Upper respiratory tract symptoms can include rhinitis, sneezing, scratchy throat, oral mucosa and laryngeal edema; lower respiratory symptoms can include cough, shortness of breath, wheezing and chest pain and an asthma like condition. S-bioallethrin caused an inhibition of human lymphocyte proliferation in 72 hr culture in a concentration dependent manner. Pyrethroids are not cholinesterase inhibitors. Pyrethrins are irritating to the eye. Skin rash on moist areas of the body have been observed. Employees with chronic respiratory and skin diseases may be at increated risk to pyrethrum exposure. Persons sensitive to rag weed may show sensitiziation to pyrethroids. Individuals may be exposed to allethrins during pesticide applications and inhalation exposures may result when consumers use space spray products, patio foggers, mosquito coils and fly mats. ANIMAL STUDIES: When undiluted and diluted technical allethrin in olive oil were applied to the dorsal skin of rabbits. No differences were noted between treated and control animals. Solutions of different concentrations of allethrin applied to the eyes of rabbits produced eyelid closure, slight conjunctival hyperemia and lacrimation. Allethrin solution applied topically to the backs of male guinea pigs and then rechallenged showed a sporadic pink color on the site of application. Histological examination revealed slight lymphocytic and monocytic infiltration of the dermis in allethrin treated animals. Bioallethrin did not produce any irritation, but produced slight sensitization in guinea pigs. It was also a slight irritant to the skin of rabbits. Rats exposed to allethrin mosquito repellant had significant increases in weights livers and adrenal gland in males, brain and thyroid in females. Changes in liver enzymes were also noted. Allethrin administered in the diets to male Wistar rats a decrease in body weight gain, and increases in liver and kidney weights were observed. Bile ductile proliferation was also noted. ICR mice exposed to a mist of d-allethrin or S-bioallethrin. No significant effects were noted in pregnant ICR mice exposed to d-allethrin or S-Bioallethrin on gestation days 7-12. Allethrin given allethrin by intubation to pregnant albino rabbits there was no evidence of compound related effects. Allethrin was strongly positive at low doses. The mutagenic potential of allethrin was examined in a wide range of tests including in vitro/in vivo gene mutation, DNA damage and repair, and in vitro/in vivo structural aberration the results of the tests were negative. Allethrin was found to be mutagenic in Salmonella typhimurium reversion assay systems in TA 100, TA 104 and TA 97 strains and required metabolic activation. Allethrin did not show evidence of treatment related effects on micronuclei frequency in mouse bone marrow smears. Fish are sensitive to allethrin toxicity when they are exposed to this insecticide in elevated water temperatures/ In plants allethrin is not phototoxic.
Both type I and type II pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (T10, T18, L857)
As for every type I pyrethroid, allethrin effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli, followed by fine tremor, prostration with coarse whole body tremor, elevated body temperature, coma, and death. Paresthesia can also occur after dermal exposure to allethrin. It is likely to be a human carcinogen by the oral route. (L857)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
暴露途径
该物质可以通过吸入其气溶胶和通过摄入被身体吸收。
The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
WHEN RADIOACTIVE PYRETHROID IS ADMIN ORALLY TO MAMMALS, IT IS ABSORBED FROM INTESTINAL TRACT OF THE ANIMALS & DISTRIBUTED IN EVERY TISSUE EXAMINED. EXCRETION OF RADIOACTIVITY IN RATS ADMIN TRANS-ISOMER: DOSAGE: 500 MG/KG; INTERVAL 20 DAYS; URINE 36%; FECES 64%; TOTAL 100%. /PYRETHROIDS/
Pyrethrins are absorbed through intact skin when applied topically. When animals were exposed to aerosols of pyrethrins with piperonyl butoxide being released into the air, little or none of the combination was systemically absorbed. /Pyrethrins/
Although limited absorption may account for the low toxicity of some pyrethroids, rapid biodegradation by mammalian liver enzymes (ester hydrolysis and oxidation) is probably the major factor responsible. Most pyrethroid metabolites are promptly excreted, at least in part, by the kidney. /Pyrethroids/
There were no major /metabolic/ differences between sexes, between low and high dose groups, nor between single-dose groups and repeated dose groups. The majority of radioactivity was eliminated within 3 days. Urinary elimination ranged from approximately 25 - 50% and fecal elimination ranged from 50 - 70%. There was no bioaccumulation of residue in tissues. ... /d-trans-Allethrin/
When allethrin labelled with (14)C in the acid moiety or with (3)H in the alcohol moiety was administered orally to male Sprague Dawley rats at levels ranging from 1 to 5 mg/kg body weight, the radiocarbon and tritium from the acid- and alcohol-labellings were eliminated in the urine (30% and 20.7%, respectively) and feces (29% and 27%, respectively) in 48 hr. ... Most of the metabolites excreted in the urine were ester-form metabolites together with two hydrolyzed products, chrysanthemum dicarboxylic acid (CDCA) and allethrolone. ...
