Oleoyl ethanolamide| CAS#111-58-0

MedKoo Cat#: 534135 | Name: Oleoyl ethanolamide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oleoyl ethanolamide (OEA), also known as AM1301, is an analog of the endocannabinoid AEA found in brain tissue and in chocolate. It is one of the long chain fatty acid ethanolamides that accumulates rapidly in infarcted tissue, but its biosynthesis is reduced in the intestine of rats following food deprivation. OEA is an endogenous, potent agonist for PPARα, exhibiting an EC50 value of 120 nM in a transactivation assay

Chemical Structure

Oleoyl ethanolamide

CAS#111-58-0 (free base)

Theoretical Analysis

MedKoo Cat#: 534135

Name: Oleoyl ethanolamide

CAS#: 111-58-0 (free base)

Chemical Formula: C20H39NO2

Exact Mass: 325.2981

Molecular Weight: 325.54

Elemental Analysis: C, 73.79; H, 12.08; N, 4.30; O, 9.83

Price and Availability

Size	Price	Availability
1g	USD 350.00	2 Weeks
2g	USD 550.00	2 Weeks
5g	USD 1,250.00	2 Weeks

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Related CAS #

111-58-0 (free base) 68511-29-5 (maleate)

Synonym

AM3101; AM-3101; AM 3101; Oleoyl Ethanolamide; N-(2-Hydroxyethyl)oleamide; N-Oleoyl-2-aminoethanol; N-Oleoylethanolamide; N-Oleoylethanolamine; Oleamide MEA; Oleic acid ethanolamide; Oleic acid monoethanolamide; Oleoylethanolamide;

IUPAC/Chemical Name

N-(2-hydroxyethyl)oleamide

InChi Key

BOWVQLFMWHZBEF-KTKRTIGZSA-N

InChi Code

InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-

SMILES Code

CCCCCCCC/C=C\CCCCCCCC(NCCO)=O

Appearance

Liquid

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oleoylethanolamide is a high affinity endogenous PPAR-α agonist.

In vitro activity:

The present study aimed to determine whether OEA treatment protects against DOX-induced cytotoxicity (DIC) and gain insights into the underlying mechanism that mediate these effects. Oleoylethanolamide treatment improved the myocardial structure in DOX-challenged mice by attenuating cardiac oxidative stress and cell apoptosis. OEA also alleviated DOX-induced oxidative stress and apoptosis dysregulation in HL-1 cardiomyocyte. Reference: Front Pharmacol. 2022 Apr 20;13:863322. https://pubmed.ncbi.nlm.nih.gov/35517792/

In vivo activity:

This study explored the effects of different OEA (oleoylethanolamide) administration schedules on the increased rewarding properties of cocaine induced by SD. In addition, this study evaluated the anti-inflammatory action of OEA pretreatment in TLR4 expression caused by SD in the cerebellum, a novel brain structure that has been involved in the development of cocaine addiction. This study observed that OEA pretreatment before SD or before conditioning prevented cocaine CPP in defeated mice. Biochemical analysis showed that OEA administration before SD decreased proinflammatory TLR4 upregulation in the cerebellum caused by social stress. Reference: Prog Neuropsychopharmacol Biol Psychiatry. 2023 Jun 8;124:110722. https://pubmed.ncbi.nlm.nih.gov/36724838/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.8	63.99

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 325.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Qin Y, Xie J, Zheng R, Li Y, Wang H. Oleoylethanolamide as a New Therapeutic Strategy to Alleviate Doxorubicin-Induced Cardiotoxicity. Front Pharmacol. 2022 Apr 20;13:863322. doi: 10.3389/fphar.2022.863322. PMID: 35517792; PMCID: PMC9065409. 2. Kwon EK, Choi Y, Yoon IH, Won HK, Sim S, Lee HR, Kim HS, Ye YM, Shin YS, Park HS, Ban GY. Oleoylethanolamide induces eosinophilic airway inflammation in bronchial asthma. Exp Mol Med. 2021 Jun;53(6):1036-1045. doi: 10.1038/s12276-021-00622-x. Epub 2021 Jun 2. PMID: 34079051; PMCID: PMC8257664. 3. González-Portilla M, Moya M, Montagud-Romero S, de Fonseca FR, Orio L, Rodríguez-Arias M. Oleoylethanolamide attenuates the stress-mediated potentiation of rewarding properties of cocaine associated with an increased TLR4 proinflammatory response. Prog Neuropsychopharmacol Biol Psychiatry. 2023 Jun 8;124:110722. doi: 10.1016/j.pnpbp.2023.110722. Epub 2023 Jan 29. PMID: 36724838. 4. Chen Z, Sun X, Li X, Liu N. Oleoylethanolamide alleviates hyperlipidaemia-mediated vascular calcification via attenuating mitochondrial DNA stress triggered autophagy-dependent ferroptosis by activating PPARα. Biochem Pharmacol. 2023 Feb;208:115379. doi: 10.1016/j.bcp.2022.115379. Epub 2022 Dec 13. PMID: 36525991.

In vitro protocol:

In vivo protocol:

1. González-Portilla M, Moya M, Montagud-Romero S, de Fonseca FR, Orio L, Rodríguez-Arias M. Oleoylethanolamide attenuates the stress-mediated potentiation of rewarding properties of cocaine associated with an increased TLR4 proinflammatory response. Prog Neuropsychopharmacol Biol Psychiatry. 2023 Jun 8;124:110722. doi: 10.1016/j.pnpbp.2023.110722. Epub 2023 Jan 29. PMID: 36724838. 2. Chen Z, Sun X, Li X, Liu N. Oleoylethanolamide alleviates hyperlipidaemia-mediated vascular calcification via attenuating mitochondrial DNA stress triggered autophagy-dependent ferroptosis by activating PPARα. Biochem Pharmacol. 2023 Feb;208:115379. doi: 10.1016/j.bcp.2022.115379. Epub 2022 Dec 13. PMID: 36525991.