1032 Tetramethrin Tetramethrin is a potent synthetic insecticide in the pyrethroid (type 1) family. A pyrethroid is a synthetic chemical compound similar to the natural chemical pyrethrins produced by the flowers of pyrethrums (Chrysanthemum cinerariaefolium and C. coccineum). Pyrethroids are common in commercial products such as household insecticides and insect repellents. In the concentrations used in such products, they are generally harmless to human beings but can harm sensitive individuals. They are usually broken apart by sunlight and the atmosphere in one or two days, and do not significantly affect groundwater quality except for being toxic to fish. (L811) 7696-12-0 83975 C19H25NO4 331.178360 The racemic isomer is a colourless crystalline solid. The (1R)-isomer is a yellow or brown viscous liquid (L870). 69°C 0.00183 mg/mL at 25°C [TOMLIN,C (1997)] Inhalation (L857) ; oral (L857) ; dermal (L857) ; eye contact (L857). 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) The reactions occuring during metabolism of tetramethrin are: ester cleavage; loss of the hydroxymethyl group from the alcohol moiety; reduction of the 1-2 bond of the alcohol moiety; oxidation at the isobutenyl methyl moiety of the acid and at the 2-, 3-, and 4-positions of the alcohol moiety; conjugation of the resultant acids and alcohols with glucuronic acid; and cis/trans isomerization. The metabolites are excreted in the urine and faeces in more or less equal amounts. (L870) LD50: 5000 mg/kg (Oral, Rat) (L870) LD50 (racemate isomer): 2000 mg/kg (Oral, Mouse) (L870) LD50 (1R-isomer): 1060 mg/kg (Oral, Mouse) (L870) No indication of carcinogenicity to humans (not listed by IARC). Pyrethroids are used as insecticides. (L857) Pyrethroid 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, severe corneal damage, hypotension and tachycardia, associated with anaphylaxis, can also occur following pyrethriod poisoning. (L857) Following oral exposure, severe fine tremor, marked reflex hyperexcitability, sympathetic activation can occur. Nausea, vomiting and abdominal pain commonly occur and develop following ingestion. Sudden bronchospasm, swelling of oral and laryngeal mucous membranes, and anaphylactoid reactions have been reported after inhalation. Hypersensitivity reactions characterized by pneumonitis, cough, dyspnea, wheezing, chest pain, irritability to sound and touch, and bronchospasm may occur too . Dermatitis is the main effect of a dermal exposure to tetramethrin. (T36) Following oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (L363) 2009-06-18T17:03:35Z 2014-12-24T20:23:04Z Tetramethrin interacts with the nicotinic acetylcholine (ACh) receptor/channel, sodium as well as calcium channels. Hepatic and extrahepatic carboxylesterases metabolize permethrin ( T18, L857, A258). C18373 39397 C009424 Tetramethrin 7851 true Liver carboxylesterase 1 (P23141) Carboxylesterase 2 (O00748) Carboxylesterase 3 (Q6UWW8) Inactive carboxylesterase 4 (Q9UKY3) Carboxylesterase 7 ( Q6NT32) Carboxylesterase 8 (Q5XG92) (T18, L857, A259) CC(C)=CC1C(C(=O)OCN2C(=O)C3=C(CCCC3)C2=O)C1(C)C C19H25NO4 InChI=1S/C19H25NO4/c1-11(2)9-14-15(19(14,3)4)18(23)24-10-20-16(21)12-7-5-6-8-13(12)17(20)22/h9,14-15H,5-8,10H2,1-4H3 InChIKey=CXBMCYHAMVGWJQ-UHFFFAOYSA-N 331.4061 331.178358293 Exogenous Solid CHEMBL1788386 75773