N-(3-Methoxybenzyl)oleamide | CAS:883715-21-7

N-(3-Methoxybenzyl)oleamide

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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:

Toxicol Appl Pharmacol, 2018, 340:67-76.

Neuroprotective activity of macamides on manganese-induced mitochondrial disruption in U-87 MG glioblastoma cells.[Reference: WebLink]

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.
METHODS AND RESULTS:
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 50 μM was responsible for mitochondrial disruption, which was attenuated by all three of the macamides tested. Human peroxisome proliferator-activated receptor gamma (PPARγ) has been proposed to be a cannabinoid target, and PPARγ has also been demonstrated to mediate some of the longer-term vascular effects of the plant cannabinoid, ∆ 9-tetrahydrocannabinol. PPARγ activation was observed in response to exposures of cells to MAC 18:2 and MAC 18:3.
CONCLUSIONS:
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 PPARγ to regulate metabolism and energy homeostasis, cell differentiation and inflammation.

N-(3-Methoxybenzyl)oleamide Description

Source:	The herbs of Lepidium meyenii Walp
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Product Name	N-(3-Methoxybenzyl)oleamide
Price:	$218 / 20mg
CAS No.:	883715-21-7
Catalog No.:	CFN90847
Molecular Formula:	C₂₆H₄₃NO₂
Molecular Weight:	401.6 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Oil
Source:	The herbs of Lepidium meyenii Walp
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Alkaloids Compound Library

	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

CFN90843	Macamide B	74058-71-2	345.6	C₂₃H₃₉NO
CFN90844	N-Benzyloleamide	883715-21-7	371.6	C₂₅H₄₁NO
CFN90842	(9Z,12Z)-N-Benzyloctadeca-9,12-dienamide	18286-71-0	369.6	C₂₅H₃₉NO
CFN90866	N-Benzyllinolenamide	883715-18-2	367.6	C₂₅H₃₇NO
CFN90846	N-(3-Methoxybenzyl)palmitamide	847361-96-0	375.6	C₂₄H₄₁NO₂
CFN90847	N-(3-Methoxybenzyl)oleamide	883715-21-7	401.6	C₂₆H₄₃NO₂
CFN90845	(9Z,12Z)-N-(3-Methoxybenzyl)octadeca-9,12-dienamide	883715-22-8	399.6	C₂₆H₄₁NO₂
CFN90179	Nonivamide	2444-46-4	293.40	C₁₇H₂₇NO₃
CFN90956	Decylic acid vanillylamide	31078-36-1	307.43	C₁₈H₂₉NO₃
CFN91684	Palvanil	69693-13-6	391.6	C₂₄H₄₁NO₃