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S-Methoprene

Alias: ZR 2458; (+)-Methoprene; Preco
Cat No.:V14949 Purity: ≥98%
S-Methoprene is a juvenile hormone analog that prevents insects from changing from pupae to adults and is used as an insecticide.
S-Methoprene
S-Methoprene Chemical Structure CAS No.: 65733-16-6
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
Other Sizes

Other Forms of S-Methoprene:

  • Methoprene
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
S-Methoprene is a juvenile hormone analog that prevents insects from changing from pupae to adults and is used as an insecticide.
S-Methoprene (CAS 65733-16-6), also known as S-(+)-Methoprene, is an insect juvenile hormone analog and an effective insecticide that blocks the transition from pupa to adult in insects. With a molecular formula of C19H34O3 and the chemical name propan-2-yl (2E,4E,7S)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate, this compound also functions as a CB1 receptor ligand. S-Methoprene inhibits the binding of the CB1 receptor antagonist [3H]CP-55940 to the CB1 receptor with an IC50 of 19.31 μM. It alters cytochrome oxidase redox activity and induces male sex differentiation.
Biological Activity I Assay Protocols (From Reference)
Targets
S-Methoprene targets multiple biological systems. As an insect juvenile hormone analog, it acts on insect hormone receptors, blocking the metamorphosis from pupa to adult. The compound also functions as a CB1 receptor ligand, inhibiting the binding of the CB1 receptor antagonist [3H]CP-55940 to the CB1 receptor with an IC50 of 19.31 μM. CB1 receptors are part of the endocannabinoid system involved in various physiological processes. Additionally, S-Methoprene alters cytochrome oxidase redox activity and induces male sex differentiation.
ln Vitro
In vitro studies demonstrate that S-Methoprene is a CB1 receptor ligand that inhibits the binding of the CB1 receptor antagonist [3H]CP-55940 with an IC50 of 19.31 μM. As an insect juvenile hormone analog, the compound alters cytochrome oxidase redox activity. The compound's effects on insect hormone receptors have been well characterized in insect cell culture systems. In mammalian cell assays, S-Methoprene's CB1 receptor binding activity has been confirmed. The compound's effects on cell signaling and gene expression related to hormone signaling have been studied.
ln Vivo
In vivo studies show that S-Methoprene is an effective insecticide that blocks the transition from pupa to adult in insects. The compound induces male sex differentiation in insects. As a juvenile hormone analog, it disrupts normal insect development and metamorphosis. The compound's efficacy as an insecticide has been demonstrated in various insect species. In mammalian systems, the compound's CB1 receptor ligand activity has been characterized, although its in vivo effects on the endocannabinoid system require further study.
Enzyme Assay
The in vitro receptor binding assay for S-Methoprene involves measuring CB1 receptor binding affinity using radioligand binding techniques. Membranes from cells expressing human CB1 receptors are incubated with varying concentrations of S-Methoprene (0.1-1000 μM) and a fixed concentration of the CB1 antagonist [3H]CP-55940. Non-specific binding is determined using excess unlabeled CP-55940. IC50 values are calculated from competition binding curves. For insect hormone receptor studies, radiolabeled juvenile hormone analogs are used in similar binding assays with insect cell membrane preparations. The compound's effects on cytochrome oxidase activity are measured using spectrophotometric assays.
Cell Assay
In vitro cellular assays for S-Methoprene typically use insect cell lines (e.g., Sf9, Drosophila cells) for juvenile hormone activity studies. Cells are treated with the compound at concentrations of 0.1-1000 μM for 24-72 hours. Gene expression changes related to metamorphosis and development are analyzed by qPCR. For CB1 receptor studies, mammalian cells expressing CB1 receptors are used. cAMP levels are measured using ELISA or HTRF-based assays to assess CB1 receptor signaling. Cell viability is assessed using MTT or CCK-8 assays. The compound's effects on cell differentiation are evaluated by morphological analysis and marker gene expression.
Animal Protocol
In vivo animal studies for S-Methoprene involve insect models for insecticide efficacy testing. Insects (e.g., mosquitoes, flies, beetles) are exposed to the compound via contact, ingestion, or topical application at various concentrations. Mortality, developmental abnormalities, and inhibition of pupal-to-adult transition are assessed. For mammalian studies, the compound's CB1 receptor ligand activity could be evaluated in rodent models, although such studies are limited. Pharmacodynamic studies in insects evaluate dose-response relationships and duration of action.
ADME/Pharmacokinetics
Pharmacokinetic properties of S-Methoprene in insects indicate good bioavailability through contact and ingestion. The compound has a molecular weight of 310.47 and molecular formula of C19H34O3. It is soluble in organic solvents. The compound should be stored at -20°C for long-term preservation. In insects, the compound is metabolized and eliminated through normal detoxification pathways. For mammalian studies, the compound's pharmacokinetics are less well characterized. Based on its lipophilic nature, the compound is expected to distribute to fatty tissues.
Toxicity/Toxicokinetics
Toxicological data for S-Methoprene indicates low toxicity to mammals, which is typical for insect juvenile hormone analogs. The compound is considered safe for use as an insecticide in various applications. However, as a CB1 receptor ligand, the compound may have effects on the endocannabinoid system. The compound is for research and agricultural use only and not for human therapeutic applications. Standard safety precautions should be followed when handling. For detailed toxicity information, safety data sheets should be consulted.
References

[1]. 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.

[2]. 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.

Additional Infomation
(S)-Methoxyprone is a methoxyprone compound, and it is the enantiomer of (R)-methoxyprone. It is a juvenile hormone analog and insect growth regulator that controls insects by interfering with their metamorphosis. It is very effective in controlling mosquito larvae.
S-Methoprene (S-(+)-Methoprene) is a research and agricultural compound with CAS number 65733-16-6. Its molecular formula is C19H34O3. The compound is an insect juvenile hormone analog and effective insecticide that blocks pupal-to-adult transition. It also functions as a CB1 receptor ligand (IC50 = 19.31 μM). The compound alters cytochrome oxidase activity and induces male sex differentiation in insects. It is not approved for therapeutic use and is strictly for research and agricultural purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H34O3
Molecular Weight
310.47
Exact Mass
310.25
CAS #
65733-16-6
Related CAS #
Methoprene;40596-69-8
PubChem CID
1711973
Appearance
Colorless to light yellow liquid
Density
0.9±0.1 g/cm3
Boiling Point
385.7±25.0 °C at 760 mmHg
Flash Point
162.4±17.8 °C
Vapour Pressure
0.0±0.9 mmHg at 25°C
Index of Refraction
1.462
LogP
5.63
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
11
Heavy Atom Count
22
Complexity
378
Defined Atom Stereocenter Count
1
SMILES
CC(C)OC(=O)/C=C(\C)/C=C/C[C@@H](C)CCCC(C)(C)OC
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
Chemical Name
propan-2-yl (2E,4E,7S)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
Synonyms
ZR 2458; (+)-Methoprene; Preco
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~322.09 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.05 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 2.5 mg/mL (8.05 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.2209 mL 16.1046 mL 32.2092 mL
5 mM 0.6442 mL 3.2209 mL 6.4418 mL
10 mM 0.3221 mL 1.6105 mL 3.2209 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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