Bioresmethrin
Identification Number: CASRN | 28434-01-7

  Substance Attributes

• Metabolic Interference or Disruption

  Interferes with human metabolism. This can be a very serious thing. Some of these interference mechanics are well established. However, often long term effects and health consequences remain largely unknown. Additionally an emerging area of concern and one that is not currently studied, is the combined synergistic effects these metabolically disrupting chemicals have on human health.

  
  

  Metabolic interference happens when the substance produces highly reactive and often damaging intermediates during detoxification or when the substance binds to specific enzymes, important structural groups on molecules, receptors and membranes or targets DNA or mimics key nutrients.

• Exposure Produces Health Symptoms

  Symptoms maybe short term or long term depending on the exposure duration and intensity and effects areas like Cardiovascular, Gastrointestinal, Cognition, Fatigue. A substance with this attribute may cause an allergic skin reaction, serious eye irritation, allergy or asthma symptoms or breathing difficulties if inhaled.

• Toxic to Wildlife

  May kill plants, fish, birds or other animals and insects or may be very toxic to aquatic life with long lasting effects. This then effects delicate environmental ecology and food supply in ways we don't fully understand yet.

These attributes are ONLY based on peer-reviewed evidence. See link to Data Sources below. Everyone benefits from knowing this stuff. Please Share.

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• CATEGORIES: Pesticide | Household Toxin | Synthetic Toxin | PESTICIDE active ingredient | Pesticide or Plant Growth Regulator Approved in Australia | A Hazardous Substance that may be found in the Australian Workplace
• SUBSTANCE LINEAGE: Organic Compounds | Lipids and Lipid-Like Molecules | Prenol Lipids | Monoterpenoids | Aromatic Monoterpenes
• SYNONYMS: (+)-trans-resmethrin | 1R-trans-Resemethrin | 5-Benzyl-3-furylmethyl (+)-trans-chrysanthemate | 5-Benzyl-3-furylmethyl (1R)-trans-chrysanthemate | Biobenzyfuroline | Resmethrin
• DESCRIPTION: Bioresmethrin is a synthetic pyrethroid (type 1) insecticide formerly used as a grain protectant. Bioresmethrin is one of the most effective broad spectrum insecticides currently available. It exhibits a high order of insecticidal activity, which when coupled with its excellent toxicological properties, makes it potentially one of the safest and most useful insecticides now being produced. 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. Insects with certain mutations in their sodium channel gene may be resistant to pyrethroid insecticides. (L811, L708, L857, L878)
• COMMENTS: Residues of this pesticide are tested for on Australian Foods | Pesticide approved in Australia
  
  From Safe Work Australia and the Hazardous Substances Information System (HSIS) in Australia:
  
  Very toxic to aquatic life with long lasting effects | Environmental Hazard | A Hazardous Substance that may be found in the Australian Workplace. Check with your employer or health and safety officer. Stay informed and become aware of the dangers that surround you. This chemical is included on the list of recognised hazardous chemicals from the Safe Work Australia - Hazardous Substances Information System (HSIS) that is based on the Globally Harmonised System of Classification and Labelling of Chemicals (GHS)
  
  Work Health and Safety (WHS) Regulations are the basis for hazardous chemicals regulations in Commonwealth, State and Territory jurisdictions in Australia. Under the model WHS Regulations, manufacturers and importers of substances, mixtures and articles supplied for use in workplaces are required to determine whether they are hazardous to health and safety before supply. The model WHS Regulations mandate that the hazards of a chemical as determined by the Globally Harmonised System of Classification and Labelling of Chemicals (GHS) must be included in safety data sheets and on labels. There are transitional arrangements in place for moving to the GHS-based system.
  
  The GHS Hazardous Chemical Information List contains chemicals classified by an authoritative source (such as the European Commission or NICNAS) in accordance with the Globally Harmonized System of Classification and Labelling of Chemicals (the GHS). This list contains the vast majority of chemicals currently in HSIS. This list and its detail are regularly updated by Work Safe Australia. The model Work Health and Safety (WHS) Regulations require chemicals to be classified in accordance with the Globally Harmonised System of Classification and Labelling of Chemicals (GHS). However transitional arrangements allow use of classification information in HSIS derived from the Approved Criteria until the 31 December 2016.
• 
• FORMULA: C22H26O3
• DATA SOURCES: DATA SOURCES: T3DB | PubChem | Compendium of Pesticide Common Names | APVMA | Safe Work Australia - Hazardous Substances Information System (HSIS)
• LAST UPDATE: 28/04/2018

  Health Associations

Mostly focused on Health Implications of Long Term Exposure to this substance

• SYMPTOMS: Following dermal exposure to bioresmethrin, feelings of numbness, itching, burning, stinging, tingling, or warmth may occur, that could last for a few hours. Dizziness, headache, nausea, muscle twitching, reduced energy, and changes in awareness can result from inhalation or ingestion of large amounts of bioresmethrin. Paralysis can occur after exposure. (L857)
• POSSIBLE HEALTH CONSEQUENCES: As for every type I pyrethroid, bioresmethrin 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. (L857) | The biodegradation of bioresmethrin is a complex phenomenon with several reactions occurring simultaneously and taking place at various positions in the molecule. The initial step in the metabolism is cleavage at the ester linkage, a reaction found to be catalyzed by esterases localized in the liver microsome. Transisomerization was reported with bioresmethrin but was apparently limited to isomerization of degradation products, not observed with the parent molecule and seen only when bioresmethrin was administered at low levels. Bioresmethrin is degraded by ester cleavage and the alcohol moiety is oxidized to 5-benzyl-3-furylmethanol (BFA), 5-benzyl-3-furoic acid (BFCA), 4'-hydroxy BFCA and alpha-hydroxy BFCA (alpha-OH-BFCA). The chrysanthemate (acid) moiety undergoes oxidation from trans-chrysanthemic acid (tE-CHA) to 2,2-dimethyl3-(2'hydroxymethyl-1'-propenyl)cyclopropanecarboxylic acid (tE-CHA) (oxidative metabolism at the methyl group of the isobutenyl side chain trans (E) to the cyclopropane). This is further oxidized through the formyl derivative (CAA) to the dicarboxylic acid isomers (tE-CDA and cE-CDA). It is at the CAA oxidation stage where isomerization may occur through the proposed aldehyde (cE-CAA) intermediate to (cE-CDA) the cis-dicarboxylic acid (Ueda et al., 1975b). This metabolic sequence may also account for the consideration of Verschoyle and Barnes (1972) that as a delay in signs of poisoning was evident following iv administration, bioresmethrin may be converted in vivo to a toxic metabolite. The presence of (+)-trans-CA,-BFA and BFCA as metabolites, which are more toxic than bioresmethrin, may account for their observation and conclusions. The metabolic sequence is very similar qualitatively to that observed with resmethrin although much less complicated because of the lack of isomeric products and because of the specificity of certain isomers to enzymatic degradation by selected routes as mentioned above. (L877)
• ACTION OF TOXIN: 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. (T18, L857) | This pyrethroid inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. (T10)
• TOXIN SITES OF ACTION IN CELL: "Membrane"
• Additional Exposure Routes: Pyrethroids are used as insecticides. (L857)

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