N-(3-Methoxybenzyl)oleamideCompetitive mGlu receptor antagonist CAS# 883715-21-7 |
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Quality Control & MSDS
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| Cas No. | 883715-21-7 | SDF | Download SDF |
| PubChem ID | 73346080 | Appearance | Oil |
| Formula | C26H43NO2 | M.Wt | 401.6 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble to 5 mM in DMSO and to 100 mM in 1.4 eq. NaOH | ||
| Chemical Name | (Z)-N-[(3-methoxyphenyl)methyl]octadec-9-enamide | ||
| SMILES | CCCCCCCCC=CCCCCCCCC(=O)NCC1=CC(=CC=C1)OC | ||
| Standard InChIKey | ZMKZIKHBSPDWEF-KHPPLWFESA-N | ||
| Standard InChI | InChI=1S/C26H43NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21-26(28)27-23-24-19-18-20-25(22-24)29-2/h10-11,18-20,22H,3-9,12-17,21,23H2,1-2H3,(H,27,28)/b11-10- | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Macamides (N-(3-methoxybenzyl)oleamide (MAC 18:1), N-(3-methoxybenzyl)linoleamide (MAC 18:2) and N-(3-methoxybenzyl)linolenamide (MAC 18:3) )achieve their neuroprotective effects by binding to CB1 receptors to protect against Mn-induced toxicity in U-87 MG glioblastoma cells. Additionally these macamides, in a manner similar to the analogous endocannabinoid AEA, interact with other targets such as PPARγ to regulate metabolism and energy homeostasis, cell differentiation and inflammation. |
| Targets | PPARγ |
| In vitro | Neuroprotective activity of macamides on manganese-induced mitochondrial disruption in U-87 MG glioblastoma cells.[Reference: WebLink]Toxicol Appl Pharmacol, 2018, 340:67-76.
Macamides are a distinct class of secondary metabolites, benzylamides of long chain fatty acids, which were isolated from the Peruvian plant Lepidium meyenii (Maca). As structural analogues of the endocannabinoid anandamide (AEA), they have demonstrated neuroprotective effects in vitro and in vivo. The purpose of this study was to demonstrate the neuroprotective activity of the macamides: N-(3-Methoxybenzyl)oleamide (MAC 18:1), N-(3-methoxybenzyl)linoleamide (MAC 18:2) and N-(3-methoxybenzyl)linolenamide (MAC 18:3) in a neurotoxic environment caused by exposure of U-87 MG glioblastoma cells to manganese chloride (MnCl2). The neuroprotective effects of these macamides were reversed by the CB1 antagonist AM251. |
N-(3-Methoxybenzyl)oleamide Dilution Calculator
N-(3-Methoxybenzyl)oleamide Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.49 mL | 12.4502 mL | 24.9004 mL | 49.8008 mL | 62.251 mL |
| 5 mM | 0.498 mL | 2.49 mL | 4.9801 mL | 9.9602 mL | 12.4502 mL |
| 10 mM | 0.249 mL | 1.245 mL | 2.49 mL | 4.9801 mL | 6.2251 mL |
| 50 mM | 0.0498 mL | 0.249 mL | 0.498 mL | 0.996 mL | 1.245 mL |
| 100 mM | 0.0249 mL | 0.1245 mL | 0.249 mL | 0.498 mL | 0.6225 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Neuroprotective activity of macamides on manganese-induced mitochondrial disruption in U-87 MG glioblastoma cells.[Pubmed:29288688]
Toxicol Appl Pharmacol. 2018 Feb 1;340:67-76.
Macamides are a distinct class of secondary metabolites, benzylamides of long chain fatty acids, which were isolated from the Peruvian plant Lepidium meyenii (Maca). As structural analogues of the endocannabinoid anandamide (AEA), they have demonstrated neuroprotective effects in vitro and in vivo. The purpose of this study was to demonstrate the neuroprotective activity of the macamides: N-(3-Methoxybenzyl)oleamide (MAC 18:1), N-(3-methoxybenzyl)linoleamide (MAC 18:2) and N-(3-methoxybenzyl)linolenamide (MAC 18:3) in a neurotoxic environment caused by exposure of U-87 MG glioblastoma cells to manganese chloride (MnCl2). The neuroprotective effects of these macamides were reversed by the CB1 antagonist AM251. The mechanism by which manganese (Mn) induces cell damage was investigated by studying its effects on mitochondria. Reactive oxygen species (ROS) increase intracellular calcium and enhance the opening of mitochondrial permeability transition pores (MPTP), which leads to decreased mitochondrial membrane potential (MMP), to disruption of mitochondria and to neuron death in neurodegenerative disorders. In this study, MnCl2 at 50muM was responsible for mitochondrial disruption, which was attenuated by all three of the macamides tested. Human peroxisome proliferator-activated receptor gamma (PPARgamma) has been proposed to be a cannabinoid target, and PPARgamma has also been demonstrated to mediate some of the longer-term vascular effects of the plant cannabinoid, 9-tetrahydrocannabinol. PPARgamma activation was observed in response to exposures of cells to MAC 18:2 and MAC 18:3. These findings suggest that macamides achieve their neuroprotective effects by binding to CB1 receptors to protect against Mn-induced toxicity in U-87 MG glioblastoma cells. Additionally these macamides, in a manner similar to the analogous endocannabinoid AEA, interact with other targets such as PPARgamma to regulate metabolism and energy homeostasis, cell differentiation and inflammation.
