ANANDAMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H37NO2
Molecular Weight	347.5347
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LGEQQWMQCRIYKG-DOFZRALJSA-N

InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-

HIDE SMILES / InChI

Molecular Formula	C22H37NO2
Molecular Weight	347.5347
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	4
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9653194 | https://www.ncbi.nlm.nih.gov/pubmed/28529018 | https://www.ncbi.nlm.nih.gov/pubmed/29277315

Anandamide, an endocannabinoid neurotransmitter, acts as a ligand of the cannabinoid receptors. It possesses anti-proliferative effect which was accompanied by a reduction of cells in the S phase of the cell cycle. Anandamide also possesses the positive effects on eating behavior and motivation in mice. Recently was discovered, that anandamide reduced cryocapacitation and improved post-thaw sperm quality in the water buffalo (Bubalus bubalis).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid receptor 8 Target ID: CHEMBL2096981 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8395053	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors.	1995 Sep	7565624
Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide.	1999 Jul 29	10440374
Levels, metabolism, and pharmacological activity of anandamide in CB(1) cannabinoid receptor knockout mice: evidence for non-CB(1), non-CB(2) receptor-mediated actions of anandamide in mouse brain.	2000 Dec	11080195
Endocannabinoids acting at vascular CB1 receptors mediate the vasodilated state in advanced liver cirrhosis.	2001 Jul	11433348
Inhibition of methamphetamine self-administration in rats by cannabinoid receptor antagonist AM 251.	2002 Jun	12095072
Cannabinoids ablate release of TNFalpha in rat microglial cells stimulated with lypopolysaccharide.	2003 Jan 15	12509806
Anandamide and vanilloid TRPV1 receptors.	2003 Nov	14517174
Cannabinoids inhibit the vascular endothelial growth factor pathway in gliomas.	2004 Aug 15	15313899
Cocaine- and amphetamine-related transcript is involved in the orexigenic effect of endogenous anandamide.	2005	16131814
Functional effects of nonsynonymous polymorphisms in the human TRPV1 gene.	2007 Dec	17913835
The orphan receptor GPR55 is a novel cannabinoid receptor.	2007 Dec	17876302
Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol.	2007 Mar	17245358
Cannabinoids ameliorate pain and reduce disease pathology in cerulein-induced acute pancreatitis.	2007 May	17484889
Anti-dyskinetic effects of cannabinoids in a rat model of Parkinson's disease: role of CB(1) and TRPV1 receptors.	2007 Nov	17900568
TRPV2 is activated by cannabidiol and mediates CGRP release in cultured rat dorsal root ganglion neurons.	2008 Jun 11	18550765
Subunit-specific modulation of glycine receptors by cannabinoids and N-arachidonyl-glycine.	2008 Oct 15	18755158
Distribution and function of cannabinoid receptors 1 and 2 in the rat, monkey and human bladder.	2009 Apr	19237169
Localization and function of cannabinoid receptors in the corpus cavernosum: basis for modulation of nitric oxide synthase nerve activity.	2010 Feb	19147270
Alterations of the endocannabinoid system in an animal model of migraine: evaluation in cerebral areas of rat.	2010 Mar	19515121
TRPV1 and TRPA1 stimulation induces MUC5B secretion in the human nasal airway in vivo.	2011 Nov	21981454
A re-evaluation of 9-HODE activity at TRPV1 channels in comparison with anandamide: enantioselectivity and effects at other TRP channels and in sensory neurons.	2012 Dec	22861649
Axonal neuropathy-associated TRPV4 regulates neurotrophic factor-derived axonal growth.	2012 Feb 17	22187434

Patents

Sample Use Guides

In Vivo Use Guide

male mice pups were treated with a daily oral dose of anandamide (AEA) 20 μg/g body weight during lactation. Adult mice were also treated with a single oral dose of AEA, to evaluate acute food intake during 4 h. At 21 and 160 days, CB1R protein abundance was calculated by western blot analysis.

Route of Administration: Oral

In Vitro Use Guide

Anandamide inhibits human breast cancer cell proliferation. Anandamide dose-dependently inhibited the proliferation of MCF-7 and EFM-19 cells with IC50 values between 0.5 and 1.5 microM and 83-92% maximal inhibition at 5-10 microM. The proliferation of several other non-mammary tumoral cell lines was not affected by 10 microM anandamide. The anti-proliferative effect of anandamide was not due to toxicity or to apoptosis of cells but was accompanied by a reduction of cells in the S phase of the cell cycle.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:14:18 GMT 2023` Edited by `admin` on `Fri Dec 15 18:14:18 GMT 2023`
Record UNII	UR5G69TJKH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANANDAMIDE

Common Name

English

N-ARACHIDONOYLETHANOLAMINE

Systematic Name

English

(5Z,8Z,11Z,14Z)-N-(2-HYDROXYETHYL)ICOSA-5,8,11,14-TETRAENAMIDE

Systematic Name

English

ANANDAMIDE [MI]

Common Name

English

ARACHIDONOYLETHANOLAMIDE

Common Name

English

Code System Code Type Description

MERCK INDEX

m1888