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N-Benzyllinolenamide

Cat No.:V28945 Purity: ≥98%
N-Benzyllinolenamide is macamide obtained from maca.
N-Benzyllinolenamide
N-Benzyllinolenamide Chemical Structure CAS No.: 883715-18-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
N-Benzyllinolenamide is macamide obtained from maca. It is a fatty amide hydrolase (FAAH) inhibitor (antagonist) with IC50 of 41.8 μM.
N-Benzyllinolenamide (CAS: 883715-18-2) is a natural macamide isolated from Lepidium meyenii (Maca). With a molecular formula of C25H37NO and a molecular weight of 367.57 g/mol, it is an amide derivative of linolenic acid, characterized by a benzyl group attached to the nitrogen atom. It is a polyunsaturated macamide.
Biological Activity I Assay Protocols (From Reference)
Targets
N-Benzyllinolenamide targets fatty acid amide hydrolase (FAAH), acting as an inhibitor with an IC50 of 41.8 µM. By inhibiting FAAH, it increases the levels of endogenous fatty acid amides, such as anandamide, which are involved in the modulation of pain, inflammation, and other physiological processes.
ln Vitro
In vitro, N-Benzyllinolenamide demonstrates potent inhibition of FAAH. Its IC50 of 41.8 µM confirms its activity as a moderate inhibitor. This activity is confirmed in enzyme assays where it inhibits the hydrolysis of FAAH substrates. Its structure allows it to interact with lipid metabolism pathways.
ln Vivo
In vivo, N-Benzyllinolenamide is believed to contribute to the biological effects of Maca, which is used traditionally for its energizing and aphrodisiac properties. By inhibiting FAAH, it may modulate the endocannabinoid system, leading to effects on mood, pain, and inflammation. It shows promise in modulating cellular responses to oxidative stress.
Enzyme Assay
The in vitro enzyme assay for N-Benzyllinolenamide involves measuring its ability to inhibit FAAH activity. The enzyme is incubated with a fluorogenic substrate in the presence of varying concentrations of the compound. The rate of substrate hydrolysis is measured, and the IC50 is calculated from the inhibition curve.
Cell Assay
In vitro cell culture studies for N-Benzyllinolenamide utilize various cell lines to study its effects. Its ability to modulate the endocannabinoid system can be studied in cells expressing FAAH and cannabinoid receptors. Its anti-inflammatory effects can be studied in macrophage cell lines by measuring cytokine production. Its effects on oxidative stress can be studied by measuring ROS levels.
Animal Protocol
In vivo animal experiments for N-Benzyllinolenamide are not extensively documented. However, its effects on pain and inflammation could be studied in rodent models. The compound would be administered orally or intraperitoneally, and endpoints such as pain threshold (e.g., tail-flick test) and inflammatory cytokine levels would be assessed. Its effects on mood and behavior could also be studied.
ADME/Pharmacokinetics
N-Benzyllinolenamide has a molecular formula of C25H37NO and a molecular weight of 367.57 g/mol. It is a solid compound that is soluble in organic solvents like DMSO. It is typically stored as a powder at -20°C for long-term stability. Its stability is maintained under recommended storage conditions. As a natural product, it is often isolated from Maca.
Toxicity/Toxicokinetics
Toxicological data for N-Benzyllinolenamide are limited, as it is a research compound. As a natural component of Maca, it is generally considered to have low toxicity. However, as a research compound, it is not intended for human therapeutic use, and comprehensive toxicity studies are not available. Standard safety precautions should be followed.
References

[1]. Macamides and their synthetic analogs: evaluation of in vitro FAAH inhibition. Bioorg Med Chem. 2013 Sep 1;21(17):5188-97.

Additional Infomation
It has been reported that sunflowers (Heliopsis helianthoides) and shepherd's purse (Lepidium meyenii) contain n-benzyl-(9z,12z,15z)-octadecyltrienamide, and relevant data are available. See also: Root (part) of shepherd's purse (Lepidium meyenii).
N-Benzyllinolenamide is a research compound with no clinical approval. It is a valuable tool for studying FAAH biology and the role of the endocannabinoid system in health and disease. Its FAAH inhibitory activity makes it a compound of interest for research into pain, inflammation, and neurological disorders.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C25H37NO
Molecular Weight
367.5674
Exact Mass
367.288
CAS #
883715-18-2
PubChem CID
68741582
Appearance
Off-white to light yellow solid powder
Density
0.943±0.06 g/cm3 (20 ºC,760 mmHg), 计算值
LogP
7.283
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
15
Heavy Atom Count
27
Complexity
430
Defined Atom Stereocenter Count
0
SMILES
CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)NCC1=CC=CC=C1
InChi Key
VCMMYRWIEZCYDK-PDBXOOCHSA-N
InChi Code
InChI=1S/C25H37NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-25(27)26-23-24-20-17-16-18-21-24/h3-4,6-7,9-10,16-18,20-21H,2,5,8,11-15,19,22-23H2,1H3,(H,26,27)/b4-3-,7-6-,10-9-
Chemical Name
(9Z,12Z,15Z)-N-benzyloctadeca-9,12,15-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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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 (~272.06 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.80 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 (6.80 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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (6.80 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.7206 mL 13.6029 mL 27.2057 mL
5 mM 0.5441 mL 2.7206 mL 5.4411 mL
10 mM 0.2721 mL 1.3603 mL 2.7206 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 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
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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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