![N-Methyl lactam (1,6-dihydro-6-methyl-7H-pyrrolo[2,3-C]pyridin-7-one)](/upload/1124/V61965.png)
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| 50mg |
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| 100mg |
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| Targets |
The precise molecular target is not well-defined, but as a peramine analog, it is believed to interact with insect chemosensory receptors or feeding regulatory pathways in the insect gut. It functions as a feeding deterrent, causing insects to stop feeding on treated plants rather than acting as a direct neurotoxin.
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| ln Vitro |
In vitro, N-Methyl lactam exhibits feeding-deterrent activity against adult weevils in laboratory bioassays. It is tested on artificial diets or leaf discs to quantify the reduction in feeding behavior. It is an analogue of the natural fungal metabolite peramine, which is known to protect grasses from insect herbivory.
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| ln Vivo |
In vivo, N-Methyl lactam is active against adult weevils (e.g., Argentine stem weevil, Listronotus bonariensis) when applied to plant foliage or incorporated into an artificial diet. It deters feeding, reducing the damage caused by the insect pest. It is less potent than the natural product peramine but serves as a useful structure-activity relationship tool.
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| Enzyme Assay |
A non-cellular assay for feeding deterrents involves a no-choice or choice feeding bioassay using an artificial diet or plant leaf discs. A known amount of N-Methyl lactam is incorporated into a small agar-based diet plug or applied to a leaf disc surface. The treated diet/disc is placed in a small container with a single adult weevil. After 24-48 hours, the amount of diet/disc consumed is measured by weighing or by visual estimation of surface area removed. The reduction in consumption compared to untreated controls is calculated as a percentage.
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| Cell Assay |
The primary insect feeding bioassay uses adult Argentine stem weevils (Listronotus bonariensis). Weevils are collected from the field or reared in the laboratory. Leaf discs (e.g., from ryegrass or corn) are treated with N-Methyl lactam by dipping in a solution of known concentration (e.g., 0.1-10 mg/mL). The treated discs are placed individually in wells of a 24-well plate with a single adult weevil per well. After 24-48 hours, the amount of leaf disc consumed is visually estimated (percentage) or measured by image analysis. The compound's feeding deterrent index (FDI) is calculated.
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| Animal Protocol |
A typical in vivo protocol involves a no-choice feeding assay. Adult weevils are starved for 4-6 hours prior to the assay. Individual weevils are placed in small plastic cups or wells with a pre-weighed artificial diet pellet containing N-Methyl lactam at a concentration of 0.01-1% w/w. After 48 hours, the remaining diet is removed, dried, and reweighed. The amount consumed is calculated, and the percentage of feeding deterrence relative to control (untreated diet) is determined. For plant studies, potted plants are sprayed with the compound and exposed to weevils in cages.
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| ADME/Pharmacokinetics |
As a research chemical and not a pharmaceutical, formal PK studies are not available. N-Methyl lactam (MW 148.16, C8H8N2O) is soluble in DMSO (5.56 mg/mL, 37.53 mM). For insect bioassays, it is typically dissolved in a small amount of DMSO and then diluted in water or ethanol for spray or diet incorporation. Its stability in the environment or within insect gut is not well-characterized.
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| Toxicity/Toxicokinetics |
Toxicology data specific to mammals is not reported. N-Methyl lactam is a research chemical and insecticide candidate, not intended for human consumption. In insect bioassays, it is effective as a feeding deterrent without causing immediate mortality, suggesting it acts specifically on insect feeding pathways rather than being broadly cytotoxic. Standard laboratory safety precautions should be observed.
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| References |
[1]. Rowan DD, et al. Effect of fungal metabolite peramine and analogs on feeding and development of argentine stem weevil (Listronotus bonariensis). J Chem Ecol. 1990 May;16(5):1683-95.
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| Additional Infomation |
N-Methyl lactam is also known as 6-methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one. It is an analogue of peramine, a pyrrolopyrazine alkaloid produced by fungal endophytes (Neotyphodium lolii) that protects perennial ryegrass from insect pests. This synthetic analogue is used for structure-activity relationship (SAR) studies to understand the key chemical features required for feeding deterrent activity. It has no pharmaceutical use or drug approval status.
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| Molecular Formula |
C8H8N2O
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| Molecular Weight |
148.16
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| Exact Mass |
148.063
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| CAS # |
116212-46-5
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| PubChem CID |
638578
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
372.1±42.0 °C at 760 mmHg
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| Melting Point |
190-192 °C
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| Flash Point |
178.8±27.9 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.626
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| LogP |
0.08
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
212
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CN1C=CC2C=CNC=2C1=O
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| InChi Key |
ZLKWLYKVKAVOMD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8N2O/c1-10-5-3-6-2-4-9-7(6)8(10)11/h2-5,9H,1H3
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| Chemical Name |
6-methyl-1H-pyrrolo[2,3-c]pyridin-7-one
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.7495 mL | 33.7473 mL | 67.4946 mL | |
| 5 mM | 1.3499 mL | 6.7495 mL | 13.4989 mL | |
| 10 mM | 0.6749 mL | 3.3747 mL | 6.7495 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.
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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