Resmethrin | CAS#10453-86-8 | insecticide

MedKoo Cat#: 461675 | Name: Resmethrin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Resmethrin is a synthetic pyrethroid insecticide used against a variety of insects.

Chemical Structure

Resmethrin

CAS#10453-86-8

Theoretical Analysis

MedKoo Cat#: 461675

Name: Resmethrin

CAS#: 10453-86-8

Chemical Formula: C22H26O3

Exact Mass: 338.1882

Molecular Weight: 338.44

Elemental Analysis: C, 78.07; H, 7.74; O, 14.18

Price and Availability

Size	Price	Availability	Quantity
250mg	USD 250.00

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Synonym

Resmethrin; Benzofuroline; Isathrine; Resmetrina;

IUPAC/Chemical Name

(5-benzylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

InChi Key

VEMKTZHHVJILDY-UHFFFAOYSA-N

InChi Code

InChI=1S/C22H26O3/c1-15(2)10-19-20(22(19,3)4)21(23)25-14-17-12-18(24-13-17)11-16-8-6-5-7-9-16/h5-10,12-13,19-20H,11,14H2,1-4H3

SMILES Code

O=C(C1C(C)(C)C1/C=C(C)\C)OCC2=COC(CC3=CC=CC=C3)=C2

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>3 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Reserpine irreversibly inhibits both human isoforms of vesicular monoamine transporter, VMAT1 and VMAT2 (Kis = 34 and 12 nM, respectively). As this leads to metabolism of monoamines, reserpine is used to experimentally deplete monoamines in animals. Reserpine inhibits the multidrug resistance protein P-glycoprotein (IC50 = 0.5 µM).

In vitro activity:

The highest dose of resmethrin testedin this study completely inhibited spermatogenesis, because of apoptosis of germ cells and spermatocytes. Significant evidence for cytotoxicity was observed in the organ cultures; however, the in vivo toxicity of resmethrin has not yet been studied in detail. Reference: Toxicol Sci. 2020 Jan 1;173(1):53-64. https://pubmed.ncbi.nlm.nih.gov/31593228/

In vivo activity:

In this study, applications of permethrin, d-phenothrin, and resmethrin to vegetation and plants were evaluated for duration of residual efficacy against adult mosquitoes. Permethrin produced 90% mortality up to 1 wk postapplication, but resmethrin produced nearly this level of mortality less than 48 hours post-application Reference: J Am Mosq Control Assoc. 2008 Dec;24(4):543-9. https://pubmed.ncbi.nlm.nih.gov/19181063/

Preparing Stock Solutions

The following data is based on the product molecular weight 338.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Park HJ, Lee WY, Zhang M, Hong KH, Park C, Kim JH, Song H. Evaluation of Resmethrin Toxicity to Neonatal Testes in Organ Culture. Toxicol Sci. 2020 Jan 1;173(1):53-64. doi: 10.1093/toxsci/kfz212. PMID: 31593228. 2. Doherty JD, Lauter CJ, Salem N Jr. Synaptic effects of the synthetic pyrethroid resmethrin in rat brain in vitro. Comp Biochem Physiol C Comp Pharmacol Toxicol. 1986;84(2):373-9. doi: 10.1016/0742-8413(86)90108-8. PMID: 2427274. 3. Huang L, Peng S, Li R, Huang D, Xie D. Case Report: Fatal Neurotoxicity Following Resmethrin Poisoning in a Child. Front Pediatr. 2021 Nov 19;9:746950. doi: 10.3389/fped.2021.746950. PMID: 34869104; PMCID: PMC8639587. 4. Amoo AO, Xue RD, Qualls WA, Quinn BP, Bernier UR. Residual efficacy of field-applied permethrin, d-phenothrin, and resmethrin on plant foliage against adult mosquitoes. J Am Mosq Control Assoc. 2008 Dec;24(4):543-9. doi: 10.2987/08-5783.1. PMID: 19181063.

In vitro protocol:

In vivo protocol:

1. Huang L, Peng S, Li R, Huang D, Xie D. Case Report: Fatal Neurotoxicity Following Resmethrin Poisoning in a Child. Front Pediatr. 2021 Nov 19;9:746950. doi: 10.3389/fped.2021.746950. PMID: 34869104; PMCID: PMC8639587. 2. Amoo AO, Xue RD, Qualls WA, Quinn BP, Bernier UR. Residual efficacy of field-applied permethrin, d-phenothrin, and resmethrin on plant foliage against adult mosquitoes. J Am Mosq Control Assoc. 2008 Dec;24(4):543-9. doi: 10.2987/08-5783.1. PMID: 19181063.

1: Soderlund DM. Resmethrin, the first modern pyrethroid insecticide. Pest Manag Sci. 2015 Jun;71(6):801-7. doi: 10.1002/ps.3881. Epub 2014 Nov 17. Review. PubMed PMID: 25124081. 2: Wang Y, Zhang P, Yang B, Liu C, Shu J. Kinetic and product study of the heterogeneous reactions of NO3 radicals with suspended resmethrin, phenothrin, and fenvalerate particles. Chemosphere. 2013 Jan;90(2):848-55. doi: 10.1016/j.chemosphere.2012.09.096. Epub 2012 Oct 24. PubMed PMID: 23102722. 3: Jankowski MD, Franson JC, Möstl E, Porter WP, Hofmeister EK. Testing independent and interactive effects of corticosterone and synergized resmethrin on the immune response to West Nile virus in chickens. Toxicology. 2010 Feb 28;269(1):81-8. doi: 10.1016/j.tox.2010.01.010. Epub 2010 Jan 22. PubMed PMID: 20096745; PubMed Central PMCID: PMC2861826. 4: Rand GM. Hazard assessment of resmethrin: I. Effects and fate in aquatic systems. Ecotoxicology. 2002 Apr;11(2):101-11. PubMed PMID: 11990766. 5: Oberhauser KS, Manweiler SA, Lelich R, Blank M, Batalden RV, de Anda A. Impacts of ultra-low volume resmethrin applications on non-target insects. J Am Mosq Control Assoc. 2009 Mar;25(1):83-93. PubMed PMID: 19432072. 6: Antwi FB, Peterson RK. Toxicity of delta-phenothrin and resmethrin to non-target insects. Pest Manag Sci. 2009 Mar;65(3):300-5. doi: 10.1002/ps.1688. PubMed PMID: 19097021. 7: Meisch MV, Dame DA, Groves RL, Nunez RD. Assessment of Anopheles quadrimaculatus response to permethrin and resmethrin by topical application. J Am Mosq Control Assoc. 1994 Sep;10(3):437-9. PubMed PMID: 7807092. 8: Doherty JD, Lauter CJ, Salem N Jr. Synaptic effects of the synthetic pyrethroid resmethrin in rat brain in vitro. Comp Biochem Physiol C. 1986;84(2):373-9. PubMed PMID: 2427274. 9: Carr WC Jr, Iyer P, Gammon DW. A dietary risk assessment of the pyrethroid insecticide resmethrin associated with its use for West Nile Virus mosquito vector control in California. ScientificWorldJournal. 2006 Feb 27;6:279-90. Review. PubMed PMID: 16518516; PubMed Central PMCID: PMC5917125. 10: Amoo AO, Xue RD, Qualls WA, Quinn BP, Bernier UR. Residual efficacy of field-applied permethrin, d-phenothrin, and resmethrin on plant foliage against adult mosquitoes. J Am Mosq Control Assoc. 2008 Dec;24(4):543-9. PubMed PMID: 19181063. 11: Wilkes WW, Lewis CN, Brown JR, Allen RA, Meisch MV. Optimized aerial applications of two resmethrin formulations against caged Anopheles quadrimaculatus. J Am Mosq Control Assoc. 2009 Jun;25(2):194-8. PubMed PMID: 19653502. 12: Paul EA, Simonin HA. Effects of naled, synergized, and non-synergized resmethrin on the swimming performance of young trout. Bull Environ Contam Toxicol. 1996 Sep;57(3):495-502. PubMed PMID: 8672078. 13: Samsonov YN, Makarov VI. Kinetics and photophysical mechanism of sunlight photolysis of unstable resmethrin and phenothrin in aerosols and thin films. Bull Environ Contam Toxicol. 1996 Jun;56(6):903-10. PubMed PMID: 8661879. 14: Paul EA, Simonin HA, Tomajer TM. A comparison of the toxicity of synergized and technical formulations of permethrin, sumithrin, and resmethrin to trout. Arch Environ Contam Toxicol. 2005 Feb;48(2):251-9. Epub 2005 Jan 11. PubMed PMID: 15696349. 15: Golenda CF, Forgash AJ. Fenvalerate cross-resistance in a resmethrin-selected strain of the house fly (Diptera: Muscidae). J Econ Entomol. 1985 Feb;78(1):19-24. PubMed PMID: 3973206. 16: Reddy MR, Spielman A, Lepore TJ, Henley D, Kiszewski AE, Reiter P. Efficacy of resmethrin aerosols applied from the road for suppressing Culex vectors of West Nile virus. Vector Borne Zoonotic Dis. 2006 Summer;6(2):117-27. PubMed PMID: 16796509. 17: Zehner JM, Simonaitis RA. The determination of BHT in resmethrin by high-pressure liquid chromatography. J Chromatogr Sci. 1976 Jul;14(7):326-7. PubMed PMID: 956323. 18: Simonaitis RA, Cail RS. Gas-liquid chromatographic determination of resmethrin in corn, cornmeal, flour, and wheat. J Assoc Off Anal Chem. 1975 Sep;58(5):1032-6. PubMed PMID: 1158823. 19: Tietze NS, Schreiber ET, Hester PG, Hallmon CF, Olson MA, Shaffer KR. Susceptibility of first instar Toxorhynchites splendens to malathion, naled and resmethrin. J Am Mosq Control Assoc. 1993 Mar;9(1):97-9. PubMed PMID: 8096872. 20: Ueda K, Gaughan LC, Casida JE. Metabolism of (+)-trans- and (+)-cis-resmethrin in rats. J Agric Food Chem. 1975 Jan-Feb;23(1):106-15. PubMed PMID: 1133269.