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Pipercide

Cat No.:V54121 Purity: ≥98%
Pipercide is an amide found in the fruits of the genus Piper.
Pipercide
Pipercide Chemical Structure CAS No.: 54794-74-0
Product category: Parasite
This product is for research use only, not for human use. We do not sell to patients.
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1mg
5mg
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Product Description
Pipercide is an amide found in the fruits of the genus Piper. Pipercide has activity against mosquito larvae. Pipercide acts on the nervous system, causing repetitive discharges in the central nerve cords. Pipercide could be utilized as a pesticide.
Pipercide (CAS 54794-74-0), also known as retrofractamide B, is an N-isobutylamide alkaloid isolated from the fruits of Piper nigrum (black pepper) and other Piper species. It belongs to the class of organic compounds known as benzodioxoles. Pipercide is a natural insecticidal amide with potent activity against various insect pests. It was first characterized as a new insecticidal amide from Piper nigrum. The compound has a molecular formula of C₂₂H₂₉NO₃ and a molecular weight of approximately 355.47 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Pipercide acts on the nervous system of insects, specifically inducing repetitive discharge on the central nerve cord. This neurotoxic mechanism disrupts normal neural signaling, leading to paralysis and death of the target insect. The compound's primary molecular targets are likely ion channels or neurotransmitter receptors in the insect nervous system, though the precise binding targets have not been fully elucidated. As an amide alkaloid, it may interact with voltage-gated sodium channels or other neuronal membrane proteins.
ln Vitro
In vitro studies have demonstrated that pipercide exhibits potent larvicidal activity against mosquito larvae. Based on 48-hour LC₅₀ values, pipercide was the most toxic compound tested against Culex pipiens pallens larvae with an LC₅₀ of 0.004 ppm. It also showed high larvicidal activity against Aedes aegypti, Aedes togoi, and Culex pipiens pallens. Pipercide demonstrated remarkable insecticidal activity against the adzuki bean weevil, with potency comparable to pyrethrin.
ln Vivo
In vivo insecticidal activity of pipercide has been demonstrated in various insect models. Topical application of pipercide to adult adzuki bean weevils resulted in significant mortality. Oral and topical administration of pipercide to Lymantria dispar and Malacosoma disstria larvae showed significant toxicity. The compound also exhibited activity against adult female mosquitoes of Culex pipiens pallens and Aedes aegypti. These in vivo studies confirm pipercide's potential as an effective insecticide for pest control applications.
Enzyme Assay
Standard insecticidal activity assays are used to evaluate pipercide. For larvicidal activity, late third or early fourth instar mosquito larvae are placed in cups containing water with various concentrations of the test compound. Mortality is recorded after 24-48 hours. LC₅₀ values are calculated by Probit analysis. For topical application assays, adult insects are treated with a microdroplet of compound solution applied to the dorsal thorax using a microapplicator. Mortality is assessed at 24-72 hours post-treatment.
Cell Assay
For in vitro cell-based studies, insect cell lines such as Sf9 (Spodoptera frugiperda) or Drosophila Schneider 2 cells may be used to evaluate cytotoxicity and neurotoxic effects. Cells are cultured in appropriate media and exposed to serial dilutions of pipercide. Cell viability is assessed using MTT or resazurin assays. Electrophysiological recordings using patch-clamp techniques on isolated insect neurons can be employed to study the compound's effects on neural excitability and repetitive discharge induction.
Animal Protocol
In vivo animal studies for pipercide typically involve insect pest models rather than mammalian models. For mosquito larvicidal assays, larvae are maintained in dechlorinated water at 25-28°C and fed with yeast or fish food. Test compounds are dissolved in acetone or DMSO and added to the water. Mortality is recorded at 24 and 48 hours. For topical application studies on adult beetles or weevils, insects are anesthetized with CO₂ and treated with compound solutions using a microsyringe.
ADME/Pharmacokinetics
Pharmacokinetic properties of pipercide have not been extensively characterized. As a lipophilic amide with a molecular weight of 355.47 g/mol, it is expected to have good membrane permeability. The compound has a density of 1.066 g/cm³ and a boiling point that suggests moderate volatility. Specific PK parameters such as absorption, distribution, metabolism, and excretion in mammals have not been reported. Further pharmacokinetic studies are needed to understand its behavior in biological systems.
Toxicity/Toxicokinetics
Toxicological data for pipercide are limited in the published literature. The compound is primarily studied as an insecticide, and its toxicity to mammals has not been comprehensively evaluated. Acute toxicity studies in non-target organisms would be necessary for environmental risk assessment. As a natural product from black pepper, it may have a relatively favorable safety profile compared to synthetic insecticides. However, systematic toxicological evaluation is required for potential applications.
References

[1]. Larvicidal activity of isobutylamides identified in Piper nigrum fruits against three mosquito species. J Agric Food Chem. 2002 Mar 27;50(7):1866-70.

[2]. The Knockdown Activity an Nervous Effect of Piercide against American Cockroach, Periplaneta Americana. Applied Entomology and Zoology. 1984 Volume 19 Issue 3 Pages 288-292.

Additional Infomation
Piperidine is a member of the benzodioxane group of compounds. It has been reported to exist in plants of the genus Piper (such as Piper mullesua), Piper eucalyptifolium, and other organisms with relevant data.
Pipercide is a research compound with insecticidal applications. No clinical trials or therapeutic uses have been reported for this compound. It has been identified in various Piper species and is used as a reference standard for natural product research. The compound's potent larvicidal activity makes it a candidate for development as a botanical insecticide. Structure-activity relationship studies of pipercide and related amides may guide the development of new insecticidal agents.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H29NO3
Molecular Weight
355.47056
Exact Mass
353.199
CAS #
54794-74-0
PubChem CID
5372162
Appearance
Typically exists as solid at room temperature
Density
1.066g/cm3
Boiling Point
573.1ºC at 760 mmHg
Melting Point
114 - 115 °C
Flash Point
300.4ºC
Index of Refraction
1.559
LogP
5.489
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
10
Heavy Atom Count
26
Complexity
496
Defined Atom Stereocenter Count
0
SMILES
CC(C)CNC(=O)\C=C\C=C\CCCC\C=C\c1ccc2OCOc2c1
InChi Key
RPOYGOULCHMVBB-ADDDGJNWSA-N
InChi Code
InChI=1S/C22H29NO3/c1-18(2)16-23-22(24)12-10-8-6-4-3-5-7-9-11-19-13-14-20-21(15-19)26-17-25-20/h6,8-15,18H,3-5,7,16-17H2,1-2H3,(H,23,24)/b8-6+,11-9+,12-10+
Chemical Name
(2E,4E,10E)-11-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4,10-trienamide
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)
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8132 mL 14.0659 mL 28.1318 mL
5 mM 0.5626 mL 2.8132 mL 5.6264 mL
10 mM 0.2813 mL 1.4066 mL 2.8132 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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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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