S-Methoprene | CAS#65733-16-6 | insect growth hormone analog

MedKoo Cat#: 540286 | Name: S-Methoprene

Featured

Description:

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

S-Methoprene is a juvenile insect growth hormone analog that prohibits the ability of the insect to change from pupae to adult. It is used to control mosquito populations. It alters Ca 2+ signaling and redox activity of cytochrome oxidase and induces male sex differentiation.

Chemical Structure

S-Methoprene

CAS#65733-16-6

Theoretical Analysis

MedKoo Cat#: 540286

Name: S-Methoprene

CAS#: 65733-16-6

Chemical Formula: C19H34O3

Exact Mass: 310.2508

Molecular Weight: 310.47

Elemental Analysis: C, 73.50; H, 11.04; O, 15.46

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 300.00	2 weeks
100mg	USD 550.00	2 weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Preco; (+)-Methoprene; ZR 2458; ZR2458; ZR-2458;

IUPAC/Chemical Name

isopropyl (S,2E,4E)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate

InChi Key

NFGXHKASABOEEW-GYMWBFJFSA-N

InChi Code

InChI=1S/C19H34O3/c1-15(2)22-18(20)14-17(4)11-8-10-16(3)12-9-13-19(5,6)21-7/h8,11,14-16H,9-10,12-13H2,1-7H3/b11-8+,17-14+/t16-/m1/s1

SMILES Code

CC(C)(OC)CCC[C@H](C)C/C=C/C(C)=C/C(OC(C)C)=O

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

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

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

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

S-Methoprene prohibits the ability of the insect to change from pupae to adult and is used as an insecticide.

In vitro activity:

This study suggests potential starting structures for developing novel CB(1) receptor blocking drugs. Chelerythrine, sanguinarine, piperonyl butoxide, and (S)-methoprene interactions were investigated with mouse brain CB(1) receptors in vitro. Chelerythrine and sanguinarine inhibited CB(1) receptor binding, while isoquinoline alkaloids and (-)-β-hydrastine were inactive. Piperonyl butoxide and (S)-methoprene also inhibited CB(1) receptor binding and were low-potency neutral antagonists. Reference: Eur J Pharmacol. 2011 Mar 1;654(1):26-32. https://pubmed.ncbi.nlm.nih.gov/21172340/

In vivo activity:

Methoprene dietary supplements, whether from larvicide or analytical standard, are effective in accelerating sexual development for male Q-flies in sterile insect technique (SIT) programs. Both analytical standard methoprene and NOMOZ larvicide accelerated sexual development in fertile and sterile male Q-flies by 2-3 days, with longer mating duration. Females did not respond to methoprene. Sterile flies had slightly shorter copula duration. Methoprene and sterilization did not affect fly longevity. Reference: J Econ Entomol. 2019 Dec 9;112(6):2842-2849. https://pubmed.ncbi.nlm.nih.gov/31400195/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	322.09

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 310.47 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. Dhopeshwarkar AS, Jain S, Liao C, Ghose SK, Bisset KM, Nicholson RA. The actions of benzophenanthridine alkaloids, piperonyl butoxide and (S)-methoprene at the G-protein coupled cannabinoid CB₁ receptor in vitro. Eur J Pharmacol. 2011 Mar 1;654(1):26-32. doi: 10.1016/j.ejphar.2010.11.033. Epub 2010 Dec 21. PMID: 21172340. 2. Hagimori I, Machida H, Goi R, Mencke N. Efficacy of imidacloprid/permethrin and fipronil/(S)-methoprene combinations against Haemaphysalis longicornis ticks evaluated under in vitro and in vivo conditions. Parasitol Res. 2005 Oct;97 Suppl 1:S120-S126. doi: 10.1007/s00436-005-1455-y. PMID: 16228268. 3. Adnan SM, Farhana I, Inskeep JR, Rempoulakis P, Taylor PW. Accelerated Sexual Maturation in Methoprene-Treated Sterile and Fertile Male Queensland Fruit Flies (Diptera: Tephritidae), and Mosquito Larvicide as an Economical and Effective Source of Methoprene. J Econ Entomol. 2019 Dec 9;112(6):2842-2849. doi: 10.1093/jee/toz214. PMID: 31400195. 4. Su T, Thieme J, Cummings R, Cheng ML, Brown MQ. Cross Resistance in S-Methoprene-Resistant Culex quinquefasciatus (Diptera: Culicidae). J Med Entomol. 2021 Jan 12;58(1):398-402. doi: 10.1093/jme/tjaa182. PMID: 32914856.

In vitro protocol:

In vivo protocol:

1. Adnan SM, Farhana I, Inskeep JR, Rempoulakis P, Taylor PW. Accelerated Sexual Maturation in Methoprene-Treated Sterile and Fertile Male Queensland Fruit Flies (Diptera: Tephritidae), and Mosquito Larvicide as an Economical and Effective Source of Methoprene. J Econ Entomol. 2019 Dec 9;112(6):2842-2849. doi: 10.1093/jee/toz214. PMID: 31400195. 2. Su T, Thieme J, Cummings R, Cheng ML, Brown MQ. Cross Resistance in S-Methoprene-Resistant Culex quinquefasciatus (Diptera: Culicidae). J Med Entomol. 2021 Jan 12;58(1):398-402. doi: 10.1093/jme/tjaa182. PMID: 32914856.

1: Wu ZW, Ye CY, Ye ZT, Zhang XX, Zhang QY, Zhang Y, Zhou J, Su HEM, Chen XY, Su T, Yu JS, Qian X. Discovery of Enantiopure (S)-Methoprene Derivatives as Potent Biochemical Pesticide Candidates. J Agric Food Chem. 2024 Oct 23. doi: 10.1021/acs.jafc.4c05795. Epub ahead of print. PMID: 39443167. 2: Johnson BJ, Hereward JP, Wilson R, Furlong MJ, Devine GJ. A review of the potential impacts of coastal mosquito control programs on Australian Stingless Bees (Apidae, Meliponini)-likely exposure pathways and lessons learned from studies on honey bees. Environ Entomol. 2024 Oct 5:nvae080. doi: 10.1093/ee/nvae080. Epub ahead of print. PMID: 39373633. 3: Ramirez-Lachmann S, Hart J, Su T, Latham M, Lesser C. COMPARATIVE LABORATORY ACTIVITY AND SEMI-FIELD EFFICACY OF OMNIPRENE® G AND ALTOSID® PELLETS AGAINST AEDES AEGYPTI. J Am Mosq Control Assoc. 2024 Aug 30. doi: 10.2987/24-7186. Epub ahead of print. PMID: 39209320. 4: Sakka MK, Jagadeesan R, Baliota GV, Nayak MK, Vontas J, Athanassiou CG. High concentrations of piperonyl butoxide (PBO) enhance toxicity of S-methoprene against the lesser grain borer, Rhyzopertha dominica. Environ Sci Pollut Res Int. 2024 Aug;31(39):51344-51352. doi: 10.1007/s11356-024-34442-z. Epub 2024 Aug 7. PMID: 39110286. 5: Lopez K, Harbison J, Irwin P, Erkapic A, Holub R, Blanco C, Paskewitz S, Clifton M, Bartholomay L. Extreme resistance to S-methoprene in field-collected Culex pipiens (Diptera: Culicidae) across the Chicago, IL region. Sci Rep. 2024 Aug 3;14(1):18001. doi: 10.1038/s41598-024-69066-3. PMID: 39097646; PMCID: PMC11297970. 6: Peralta JA, Carithers DS, Beugnet F, Lappin MR. Fipronil and (S)-methoprene can lessen the risk of transmission of Bartonella clarridgeiae among cats with exposure to Ctenocephalides felis. Am J Vet Res. 2024 Jul 9;85(9):ajvr.24.04.0102. doi: 10.2460/ajvr.24.04.0102. PMID: 38984890. 7: Bibbs CS, Sorensen RB, Faraji A, White GS. A Case Report on Product Rotation to Manage Severe Lysinibacillus sphaericus Resistance in Culex pipiens from Salt Lake City, Utah. J Am Mosq Control Assoc. 2024 Jun 1;40(2):121-124. doi: 10.2987/24-7172. PMID: 38660965. 8: Hu W, Chen Y, Liang Y, Su T, Liu Q, Li X, Liu X. Laboratory and Semi-Field Evaluation on S-Methoprene Formulations Against Anopheles sinensis (Diptera: Culicidae) - Yuxi City, Yunnan Province, China. China CDC Wkly. 2024 Feb 9;6(6):105-108. doi: 10.46234/ccdcw2024.023. PMID: 38406635; PMCID: PMC10883317. 9: Jiang Y, Burroughs S. Interactive Effects of Salinity and Mosquito Larvicides Toxicity to Larvae of Aedes Taeniorhynchus. J Am Mosq Control Assoc. 2024 Mar 1;40(1):26-31. doi: 10.2987/23-7151. PMID: 38369954. 10: Rathnasekara RP, Rustum AM. Simultaneous determination of praziquantel, fipronil, eprinomectin, (S)-methoprene, their key related substances and butylated hydroxytoluene (BHT) in a topical veterinary drug product by a single stability indicating high performance liquid chromatography method. J Pharm Biomed Anal. 2024 Jan 20;238:115805. doi: 10.1016/j.jpba.2023.115805. Epub 2023 Oct 19. PMID: 37948779. 11: Su T. Comparative Activity And Efficacy of Sumilarv 0.5G and Altosid Xr Briquet Against Culex Quinquefasciatus and Aedes Aegypti in Simulated Catch Basins. J Am Mosq Control Assoc. 2023 Sep 1;39(3):173-182. doi: 10.2987/23-7134. PMID: 37796736. 12: Su T, Yu JS, Zhang Y, Qian X, Su H. Comparative bioactivity of S-methoprene and novel S-methobutene against mosquitoes (Diptera: Culicidae). J Med Entomol. 2023 Nov 14;60(6):1357-1363. doi: 10.1093/jme/tjad110. PMID: 37616574. 13: Sakka MK, Ioannou CS, Papadopoulos NT, Athanassiou CG. Residual efficacy of selected larvicides against Culex pipiens pipiens (Diptera: Culicidae) under laboratory and semi-field conditions. Environ Sci Pollut Res Int. 2023 Mar;30(14):40931-40941. doi: 10.1007/s11356-022-24654-6. Epub 2023 Jan 10. PMID: 36626059; PMCID: PMC10067649. 14: Johnson HE, Clifton M, Harbison JE, Erkapic A, Barrett-Wilt GA, Paskewitz S, Bartholomay L. Assessment of Truck-Mounted Area-Wide S-methoprene Applications to Manage West Nile Virus Vector Species in the Suburbs of Chicago, IL, USA. J Med Entomol. 2023 Mar 6;60(2):384-391. doi: 10.1093/jme/tjac170. PMID: 36484651. 15: Su T, Su H. Evaluation on the Activity and Efficacy of Omniprene™ WSP and XWSP Against the Southern House Mosquito Culex quinquefasciatus in Simulated Catch Basins. J Am Mosq Control Assoc. 2022 Dec 1;38(4):268-275. doi: 10.2987/22-7091. PMID: 36318782. 16: Mihalca AD, Deak G, Panait LC, Rabei Ș, Beugnet F. Efficacy of afoxolaner (NexGard®) against natural infestations with Trichodectes canis in dogs under field conditions. Parasit Vectors. 2022 Sep 7;15(1):317. doi: 10.1186/s13071-022-05428-y. PMID: 36071527; PMCID: PMC9450229. 17: Györke A, Dumitrache MO, Ursache AL, D'Amico G, Mircean V. Case Report: Notoedric Mange and Aelurostrongylidosis in Two Domestic Cats From Rural Environment in Romania. Front Vet Sci. 2022 Jun 1;9:849525. doi: 10.3389/fvets.2022.849525. PMID: 35720839; PMCID: PMC9200890. 18: Cutolo AA, Jardina DTG, De Vito GG, Grisi do Nascimento C, Heidmann MJ, Ferreira Nantes JD, Bassetto KV, Chagas IC, Pereira Junior EF, de Castro BG, Tielemans E. Efficacy of two endectoparasiticide products combining fipronil and (S)-methoprene or esafoxolaner with eprinomectin and praziquantel against fleas and intestinal helminths in cats naturally infested in Brazil. Parasite. 2022;29:12. doi: 10.1051/parasite/2022012. Epub 2022 Mar 3. PMID: 35238771; PMCID: PMC8893013. 19: Zanet S, Morelli S, Di Cesare A, Bò S, Traversa D, Lebon W, Beugnet F, Simonato G, Ferroglio E. Efficacy of fipronil/(S)-methoprene/eprinomectin/praziquantel (Broadline®) against Thelazia callipaeda in naturally infected cats. Parasit Vectors. 2021 Sep 15;14(1):477. doi: 10.1186/s13071-021-04983-0. PMID: 34526129; PMCID: PMC8442459. 20: European Food Safety Authority (EFSA). Scientific support for preparing an EU position for the 52nd Session of the Codex Committee on Pesticide Residues (CCPR). EFSA J. 2021 Aug 17;19(8):e06766. doi: 10.2903/j.efsa.2021.6766. PMID: 34429776; PMCID: PMC8370139.