LINOLEIC MONOETHANOLAMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H37NO2
Molecular Weight	323.5133
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=KQXDGUVSAAQARU-HZJYTTRNSA-N

InChI=1S/C20H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h6-7,9-10,22H,2-5,8,11-19H2,1H3,(H,21,23)/b7-6-,10-9-

HIDE SMILES / InChI

Molecular Formula	C20H37NO2
Molecular Weight	323.5133
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	2
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28631495 | https://www.ncbi.nlm.nih.gov/pubmed/20817522 | https://www.ncbi.nlm.nih.gov/pubmed/21296126

Linoleic monoethanolamide (or linoleoyl ethanolamide), an endocannabinoid, which weakly binds to CB1 and CB2 receptors. It was used as a neuroprotective agent in a rat model for stroke and acted through an intracellular mechanism independent of the classic endocannabinoid pathways. In addition, was shown, that linoleoyl ethanolamide was not useful in assessing pain in patients with chronic pancreatic diseases and it couldn’t replace a simple method such as a visual analogic scale for assessing the pain and its intensity.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid receptor 1 30 Target ID: P21554\|\|\|Q5UB37 Gene ID: 1268.0 Gene Symbol: CNR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9876105	Agonist 2678		10.0 µM [Ki]
Cannabinoid receptor 2 27 Target ID: P34972 Gene ID: 1269.0 Gene Symbol: CNR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9876105	Agonist 2678		25.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Stroke 144 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21296126	Preventing		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Novel analogues of arachidonylethanolamide (anandamide): affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability.	1998 Dec 31	9876105
Fatty acid amide signaling molecules.	2010 Oct 15	20817522
Lauroylethanolamide and linoleoylethanolamide improve functional outcome in a rodent model for stroke.	2011 Apr 4	21296126
Role of anorectic N-acylethanolamines in intestinal physiology and satiety control with respect to dietary fat.	2014 Aug	24681513
Serum endocannabinoids in assessing pain in patients with chronic pancreatitis and in those with pancreatic ductal adenocarcinoma.	2017 Oct	28631495
Increased plasma oleoylethanolamide and palmitoleoylethanolamide levels correlate with inflammatory changes in alcohol binge drinkers: the case of HMGB1 in women.	2018 Nov	29178411

Sample Use Guides

In Vivo Use Guide

Male Sprague Dawley rats pretreatment, 6 hours and 30 minutes with inoleoylethanolamide (NAE 18:2) before middle cerebral artery occlusion.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:36:17 GMT 2023` Edited by `admin` on `Fri Dec 15 18:36:17 GMT 2023`
Record UNII	889DYX0816
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LINOLEIC MONOETHANOLAMIDE

Common Name

English

9,12-OCTADECADIENAMIDE, N-(2-HYDROXYETHYL)-, (Z,Z)-

Systematic Name

English

N-LINOLEOYLETHANOLAMINE

Systematic Name

English

LINOLEAMIDE, N-(2-HYDROXYETHYL)-

Systematic Name

English

LINOLEIC ACID MONOETHANOLAMIDE

Common Name

English

LINOLEOYL MONOETHANOLAMIDE

Common Name

English

LINOLEAMIDE MEA

Official Name

English

LINOLEAMIDE MEA [INCI]

Common Name

English

9,12-OCTADECADIENAMIDE, N-(2-HYDROXYETHYL)-, (9Z,12Z)-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID10887223