tetramethrin
3,4,5,6-tetrahydrophthalimidomethyl cis and trans dl chrysanthemummonocarboxylic acid
 
Notes:
None found
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(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate (Click)
CAS Number: 7696-12-0Picture of molecule
Other: 28643-67-6
ECHA EINECS - REACH Pre-Reg: 231-711-6
FDA UNII: Z72930Q46K
Nikkaji Web: J4.417B
Beilstein Number: 8807938
MDL: MFCD00084635
XlogP3-AA: 4.70 (est)
Molecular Weight: 331.41205000
Formula: C19 H25 N O4
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: antimicrobial agents
 
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Physical Properties:
Appearance: colorless crystals (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 69.00 °C. @ 760.00 mm Hg
logP (o/w): 4.730
Soluble in:
 water, 1.83 mg/L @ 25 °C (exp)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antimicrobial agents
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Suppliers:
BOC Sciences
For experimental / research use only.
Tetramethrin (Mixture of Cis and Trans Isomers) > 95%
Odor: characteristic
Use: Tetramethrin, belonging to pyrethroid family, is a fast working contact insecticide used in large-scale commercial agricultural applications as well as in consumer products for domestic purposes.
Santa Cruz Biotechnology
For experimental / research use only.
Tetramethrin
Sigma-Aldrich
For experimental / research use only.
Tetramethrin PESTANAL®, analytical standard
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antimicrobial agents
Recommendation for tetramethrin usage levels up to:
 not for fragrance use.
 
Recommendation for tetramethrin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
NIOSH International Chemical Safety Cards: search
NLM Hazardous Substances Data Bank: Search
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 83975
National Institute of Allergy and Infectious Diseases: Data
WISER: UN 3077
WGK Germany: 2
 (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
Chemidplus: 0007696120
EPA/NOAA CAMEO: hazardous materials
RTECS: GZ172 000 for cas# 7696-12-0
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References:
 (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 83975
Pubchem (sid): 134988868
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C18373
HMDB (The Human Metabolome Database): Search
Haz-Map: View
Household Products: Search
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
 bioneopynamin
N-(chrysanthemoxymethyl)-1-cyclohexene-1,2-dicarboximide
 cyclohex-1-ene-1,2-dicarboximidomethyl (+-)-cis-trans-chrysanthemate
(1-cyclohexane-1,2-dicarboximido)methyl chrysanthemumate
1-(cyclohexene-1,2-dicarboximido)methyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
1-cyclohexene-1,2-dicarboximidomethyl-2,2-dimethyl-3-(2-methylpropenyl)cyclopropane carboxylate
2,2-dimethyl-3-(2-methyl-1-propenyl) cyclopropane carboxylic acid (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)methyl ester
2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)methyl ester
2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic acid ester withN-(hydroxymethyl)-1-cyclohexene-1,2-dicarboximide
(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl) methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
 insectol
 multicide
 neo-pynamin
 neopinamin
 neopynamin forte
 niagara nia-9260
 phthalthrin
 py-kill
 SP-1103
 sumitomo SP-1103
3,4,5,6-tetrahydro-phthalimidomethylester der dl-cis-trans-chrysanthemumsaeure
N-(3,4,5,6-tetrahydrophthalimide)methyl-cis,trans-chrysanthemate
N-(3,4,5,6-tetrahydrophthalimido)-methyl dl-cis-trans-chrysanthemate
3,4,5,6-tetrahydrophthalimidomethyl (+-)-cis-trans-chrysanthemate
3,4,5,6-tetrahydrophthalimidomethyl cis and trans dl chrysanthemummonocarboxylic acid
2,3,4,5-tetrahydrophthalimidomethylchrysanthemate
 tetralate
 tetramethrin [ANSI:BSI:ISO]
 tetramethrinum
 tetrametrina
 weo-pynamin
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Articles:
PubMed: Efficacy assessment of biocides or repellents for the control of Sarcoptes scabiei in the environment.
PubMed: Glucocorticoid-like activity of propylparaben, butylparaben, diethylhexyl phthalate and tetramethrin mixtures studied in the MDA-kb2 cell line.
PubMed: Pyrethroids differentially alter voltage-gated sodium channels from the honeybee central olfactory neurons.
PubMed: Determination of seven pyrethroids biocides and their synergist in indoor air by thermal-desorption gas chromatography/mass spectrometry after sampling on Tenax TA ® passive tubes.
PubMed: A sensitive monoclonal antibody-based enzyme-linked immunosorbent assay for the detection of bifenthrin in a chemical soil barrier.
PubMed: Enantiomeric-selective determination of pyrethroids: application to human samples.
PubMed: A multi-residue method for the simultaneous analysis in indoor dust of several classes of semi-volatile organic compounds by pressurized liquid extraction and gas chromatography/tandem mass spectrometry.
PubMed: Dislodgement effect of natural semiochemicals released by disturbed triatomines: a possible alternative monitoring tool.
PubMed: Molecular docking revealed potential disruptors of glucocorticoid receptor-dependent reporter gene expression.
PubMed: Two-step microextraction combined with high performance liquid chromatographic analysis of pyrethroids in water and vegetable samples.
PubMed: Multiresidue pesticide analysis of botanical dietary supplements using salt-out acetonitrile extraction, solid-phase extraction cleanup column, and gas chromatography-triple quadrupole mass spectrometry.
PubMed: Subacute oral toxicity of combinations of selected synthetic pyrethroids, piperonyl butoxide, and tetramethrin in rats.
PubMed: Hollow fibre-based liquid-phase microextraction technique combined with gas chromatography-mass spectrometry for the determination of pyrethroid insecticides in water samples.
PubMed: Use of the HS-PTR-MS for online measurements of pyrethroids during indoor insecticide treatments.
PubMed: Determination of six pyrethroid insecticides in fruit juice samples using dispersive liquid-liquid microextraction combined with high performance liquid chromatography.
PubMed: Comparison of the performance of conventional, temperature-controlled, and ultrasound-assisted ionic liquid dispersive liquid-liquid microextraction combined with high-performance liquid chromatography in analyzing pyrethroid pesticides in honey samples.
PubMed: [Study on contamimation of endocrine disrupting chemicals in aquatic environment of Qiantang River].
PubMed: Determination of pyrethroid metabolites in human urine using liquid phase microextraction coupled in-syringe derivatization followed by gas chromatography/electron capture detection.
PubMed: A use-dependent sodium current modification induced by type I pyrethroid insecticides in honeybee antennal olfactory receptor neurons.
PubMed: Simultaneous determination of 16 pyrethroid residues in tea samples using gas chromatography and ion trap mass spectrometry.
PubMed: Irritability and repellency of synthetic pyrethroids on an Aedes aegypti population from Thailand.
PubMed: Malignant mammary tumor in female dogs: environmental contaminants.
PubMed: Assessing hormone receptor activities of pyrethroid insecticides and their metabolites in reporter gene assays.
PubMed: A rapid and sensitive analytical method for the determination of 14 pyrethroids in water samples.
PubMed: Repeated-dose 14-day dermal toxicity of different combinations of some synthetic pyrethroid insecticides, piperonyl butoxide, and tetramethrin in rats.
PubMed: Simultaneous determination of nine pyrethroids in indoor insecticide products by capillary gas chromatography.
PubMed: Household exposure to pesticides and bladder exstrophy in a newborn baby boy: a case report and review of the literature.
PubMed: Acute toxicity to zebrafish of two organophosphates and four pyrethroids and their binary mixtures.
PubMed: Simultaneous determination of 18 pyrethroids in indoor air by gas chromatography/mass spectrometry.
PubMed: Comparative efficacy of spinosad with conventional acaricides against hard and soft tick populations from Antalya, Turkey.
PubMed: Use of biocidal products (insect sprays and electro-vaporizer) in indoor areas--exposure scenarios and exposure modeling.
PubMed: Pyrethroid insecticides: isoform-dependent hydrolysis, induction of cytochrome P450 3A4 and evidence on the involvement of the pregnane X receptor.
PubMed: Dynamics of esterase alleles in Culex pipiens complex mosquitoes in Beijing.
PubMed: Direct chiral resolution and its application to the determination of the pesticide tetramethrin in soil by high-performance liquid chromatography using polysaccharide-type chiral stationary phase.
PubMed: Pyrethroids as promising marine antifoulants: laboratory and field studies.
PubMed: Control of aggregated populations of the eye fly Siphunculina funicola (diptera: chloropidae) using pyrethroid aerosols.
PubMed: Developmentally-regulated sodium channel subunits are differentially sensitive to alpha-cyano containing pyrethroids.
PubMed: Acute toxicity of organophosphorus and pyrethroid insecticides to Bombyx mori.
PubMed: Orthogonal signal correction-partial least squares method for simultaneous spectrophotometric determination of cypermethrin and tetramethrin.
PubMed: Differential pharmacology of the cardiac anionic background current I(AB).
PubMed: Identification and quantitation of pyrethroid pesticide residues in vegetables by solid-phase extraction and liquid chromatography/electrospray ionization ion trap mass spectrometry.
PubMed: Comparison of two partial least squares infrared spectrometric methods for the quality control of pediculosis lotions.
PubMed: Behavioral-based educational intervention directed toward Egyptian agricultural families to protect children from pesticide exposure.
PubMed: Toxicity of pyrethroids and repellency of diethyltoluamide in two deltamethrin-resistant colonies of Triatoma infestans Klug, 1834 (Hemiptera: Reduviidae).
PubMed: Comparison of different mass spectrometric detection techniques in the gas chromatographic analysis of pyrethroid insecticide residues in soil after microwave-assisted extraction.
PubMed: Assessment of estrogenic and androgenic activities of tetramethrin in vitro and in vivo assays.
PubMed: Biomarker of pyrethrum exposure.
PubMed: Distribution of pesticide residues within homes in central New York State.
PubMed: Microelectrode array recordings of cardiac action potentials as a high throughput method to evaluate pesticide toxicity.
PubMed: Simultaneous determination of pyrethroid and pyrethrin metabolites in human urine by gas chromatography-high resolution mass spectrometry.
PubMed: Assessing estrogenic activity of pyrethroid insecticides using in vitro combination assays.
PubMed: Differential effects of pyrethroids on volume-sensitive anion and organic osmolyte pathways.
PubMed: Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection.
PubMed: Characterisation of gene expression patterns in 22RV1 cells for determination of environmental androgenic/antiandrogenic compounds.
PubMed: [The simultaneous determination of permethrin and tetramethrin in their mixed mothproofer formulation by GC].
PubMed: Kinetics of modulation of tetrodotoxin-sensitive and tetrodotoxin-resistant sodium channels by tetramethrin and deltamethrin.
PubMed: Actions of pyrethroid insecticides on sodium currents, action potentials, and contractile rhythm in isolated mammalian ventricular myocytes and perfused hearts.
PubMed: Interaction of tetramethrin and deltamethrin at the single sodium channel in rat hippocampal neurons.
PubMed: Indoor thermal fogging application of pesguard FG 161, a mixture of d-tetramethrin and cyphenothrin, using portable sprayer against vector mosquitoes in the tropical environment.
PubMed: Temperature dependence of pyrethroid modification of single sodium channels in rat hippocampal neurons.
PubMed: Supercritical-fluid extraction of synthetic pyrethroids from wool.
PubMed: Evaluation of four pediculicides against the head lice Pediculus h. capitis.
PubMed: Asthma to tetramethrin.
PubMed: Indoor behavior and risk assessment following residual spraying of d-phenothrin and d-tetramethrin.
PubMed: Indoor behavior and risk assessment following space spraying of d-tetramethrin and d-resmethrin.
PubMed: Potent modulation of tetrodotoxin-sensitive and tetrodotoxin-resistant sodium channels by the type II pyrethroid deltamethrin.
PubMed: Metabolism of tetramethrin isomers in rat: IV. Tissues responsible for formation of reduced and hydrated metabolites.
PubMed: Selective extraction of pyrethroid pesticide residues from milk by solid-matrix dispersion.
PubMed: Clean-up of aqueous acetone vegetable extracts by solid-matrix partition for pyrethroid residue determination by gas chromatography-electron-capture detection.
PubMed: [Analysis of the stereoisomers of 14 pyrethroids by capillary gas chromatography].
PubMed: Voltammetric determination of the synthetic pyrethroid insecticide tetramethrin in acetonitrile.
PubMed: Modulation of sodium channels of rat cerebellar Purkinje neurons by the pyrethroid tetramethrin.
PubMed: Differential effects of the pyrethroid tetramethrin on tetrodotoxin-sensitive and tetrodotoxin-resistant single sodium channels.
PubMed: Interactions of tetramethrin, fenvalerate and DDT at the sodium channel in rat dorsal root ganglion neurons.
PubMed: Metabolism of tetramethrin isomers in rat. III. Stereochemistry of reduced metabolites.
PubMed: Sodium channels and GABAA receptor-channel complex as targets of environmental toxicants.
PubMed: Selective block of tetramethrin-modified sodium channels by (+/-)-alpha-tocopherol (vitamin E).
PubMed: Multiresidue liquid chromatographic method for simultaneous determination of pyrethroid insecticides in fruits and vegetables.
PubMed: Role of T-type Ca2+ channel inhibitors in the pacemaker depolarization in rabbit sino-atrial nodal cells.
PubMed: Non-neurogenic contractions in isolated coronary arteries by brief electrical pulses.
PubMed: Metabolism of tetramethrin isomers in rat: II. Identification and quantitation of metabolites.
PubMed: [Statistical description of health complaints after pyrethroid exposure].
PubMed: Differential mechanism of action of the pyrethroid tetramethrin on tetrodotoxin-sensitive and tetrodotoxin-resistant sodium channels.
PubMed: Metabolism of tetramethrin isomers in rat. I. Identification of a sulphonic acid type of conjugate and reduced metabolites.
PubMed: [Comprehensive study on the membrane currents of porcine granulosa cells in culture].
PubMed: Effects of omega-conotoxin on adrenergic, cholinergic and NANC neurotransmission in the rabbit urethra and detrusor.
PubMed: Membrane currents of porcine granulosa cells in primary culture: characterization and effects of luteinizing hormone.
PubMed: Role of calcium fluxes in the action of glucagon on glucose metabolism in rat hepatocytes.
PubMed: Comparison of two sampling methods for domestic populations of Triatoma infestans in north-west Argentina.
PubMed: Calcium channels at the adrenergic neuroeffector junction in the rabbit ear artery.
PubMed: [New medical disinfectants].
PubMed: Oscillation of cytoplasmic free calcium concentration induced by insulin-like growth factor I.
PubMed: Possible requirement of serum progression factors for transformation of BALB/c 3T3 fibroblasts by v-ras p21.
PubMed: Insulin-like growth factor-I stimulates diacylglycerol production via multiple pathways in Balb/c 3T3 cells.
PubMed: Antagonism by nifedipine of contraction and Ca2(+)-influx evoked by ATP in guinea-pig urinary bladder.
PubMed: [The appearance of insecticide resistance in Blattella germanica in the German Democratic Republic].
PubMed: [The mutagenicity of some insecticides in the Salmonella/microsome test system].
PubMed: [Toxicology and hygienic standardization of the new insecticide neopinamine].
PubMed: The toxicokinetics of (1R, cis)- and (1R, trans)- tetramethrin in the isolated perfused rat liver.
PubMed: The pharmacokinetics and metabolism of (1R, cis)- and (1R, trans)-tetramethrin in rats.
PubMed: [Calcium influx: an intracellular message of the mitogenic action of insulin-like growth factors].
PubMed: Interaction of the pyrethroid insecticides tetramethrin and cypermethrin with enteric cholinergic transmission in the guinea-pig.
PubMed: Interactions of the pyrethroid fenvalerate with nerve membrane sodium channels: temperature dependence and mechanism of depolarization.
PubMed: Calcium influx: an intracellular message of the mitogenic action of insulin-like growth factor-I.
PubMed: Chemical modification of sodium channel inactivation: separate sites for the action of grayanotoxin and tetramethrin.
PubMed: Contribution of two types of calcium currents to the pacemaker potentials of rabbit sino-atrial node cells.
PubMed: Insulin-like growth factor II stimulates calcium influx in competent BALB/c 3T3 cells primed with epidermal growth factor. Characteristics of calcium influx and involvement of GTP-binding protein.
PubMed: Encounter the poultry red mite resistance to acaricides in Czechoslovak poultry-farming.
PubMed: Effect of three pyrethroids on blood feeding and fecundity of Aedes aegypti.
PubMed: Ion permeation and selectivity of squid axon sodium channels modified by tetramethrin.
PubMed: Detection of the resistance in cockroaches Blattella germanica (L.) from ships to insecticides used.
PubMed: Nerve membrane ionic channels as the target of toxicants.
PubMed: Toxins that modulate the sodium channel gating mechanism.
PubMed: Elaboration and testing of insecticidal varnish in aerosol containers for the control of synanthropic cockroaches.
PubMed: Modulators acting on sodium and calcium channels: patch-clamp analysis.
PubMed: [Evaluation of the reproductive function of rats exposed to the insecticide neopinamine].
PubMed: First case of introduction of the tick Rhipicephalus sanguineus to Czechoslovakia.
PubMed: Susceptibility of the Danish housefly, Musca domestica Linné to pyrethroid.
PubMed: Simultaneous determination of neopynamine and piperonyl butoxide by capillary column gas-liquid chromatography.
PubMed: Susceptibility to DDT and some other insecticides of head lice (Pediculus capitis De Geer) in Czechoslovakia.
PubMed: Voltage-dependent calcium block of normal and tetramethrin-modified single sodium channels.
PubMed: Drug-ionic channel interactions: single-channel measurements.
PubMed: Modification of single sodium channels by the insecticide tetramethrin.
PubMed: Gas-liquid chromatographic screening method for six synthetic pyrethroid insecticides.
PubMed: Insecticidal properties of permethrin and permethrin-based agents.
PubMed: A new pyrethroid insecticide with remarkable potency on nerve axons.
PubMed: Analysis of established pyrethroid insecticides.
PubMed: Cellular and molecular mechanisms of action of insecticides: neurophysiological approach.
PubMed: Dose-dependent interaction of the pyrethroid isomers with sodium channels of squid axon membranes.
PubMed: Glutathione conjugate of the pyrethroid tetramethrin.
PubMed: Preparation and study of composite insecticido-repellent aerosols.
PubMed: Modification of nerve membrane sodium channels by the insecticide pyrethroids.
PubMed: Kinetics of sodium channel modification by the insecticide tetramethrin in squid axon membranes.
PubMed: Modification of sodium channel kinetics by the insecticide tetramethrin in crayfish giant axons.
PubMed: Modulation of nerve membrane sodium channels by chemicals.
PubMed: Residual toxicity of wall-sprayed organophosphates, carbamates and pyrethroids to mosquito Culex pipiens molestus Forskal.
PubMed: An introduction to the metabolism of pyrethroids.
PubMed: Degradation, metabolism and toxicity of synthetic pyrethroids.
PubMed: Development of new synthetic pyrethroids.
PubMed: A verandah-trap hut for studying the house-frequenting habits of mosquitoes and for assessing insecticides. IV. The effect of tetramethrin on the behaviour and mortality of Anopheles gambiae Giles.
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