tetramethrin
3,4,5,6-tetrahydrophthalimidomethyl cis and trans dl chrysanthemummonocarboxylic acid
Identification
| Name | tetramethrin |
| CAS Number | 7696-12-0 |
| EINECS | 231-711-6 |
| FDA UNII | Z72930Q46K |
| Molecular Formula | C19 H25 N O4 |
| Molecular Weight | 331.41205000 |
| MDL Number | MFCD00084635 |
| Nikkaji Number | J4.417B |
| Beilstein | 8807938 |
Regulatory
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) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | antimicrobial agents |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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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Potential Uses
Natural Occurrence
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
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.