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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 of ANANDAMIDE

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

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).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Molecular characterization of a peripheral receptor for cannabinoids.
1993 Sep 2
Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors.
1995 Jun 29
A comparison of delta 9-THC and anandamide induced c-fos expression in the rat forebrain.
1998 Aug 17
Cannabinoid-induced mesenteric vasodilation through an endothelial site distinct from CB1 or CB2 receptors.
1999 Nov 23
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
Induction of vanilloid receptor channel activity by protein kinase C.
2000 Dec 21-28
Direct inhibition of T-type calcium channels by the endogenous cannabinoid anandamide.
2001 Dec 17
The endocannabinoid anandamide is a direct and selective blocker of the background K(+) channel TASK-1.
2001 Jan 15
Endocannabinoids acting at vascular CB1 receptors mediate the vasodilated state in advanced liver cirrhosis.
2001 Jul
Protective effects of cannabinoid receptor agonists against cocaine and other convulsant-induced toxic behavioural symptoms.
2001 Nov
Lipopolysaccharide downregulates fatty acid amide hydrolase expression and increases anandamide levels in human peripheral lymphocytes.
2001 Sep 15
Inhibition of methamphetamine self-administration in rats by cannabinoid receptor antagonist AM 251.
2002 Jun
Acidic nonsteroidal anti-inflammatory drugs inhibit rat brain fatty acid amide hydrolase in a pH-dependent manner.
2003 Feb
Cannabinoids ablate release of TNFalpha in rat microglial cells stimulated with lypopolysaccharide.
2003 Jan 15
Reduction of human monocytic cell neurotoxicity and cytokine secretion by ligands of the cannabinoid-type CB2 receptor.
2003 Jun
Anandamide and vanilloid TRPV1 receptors.
2003 Nov
AMG 9810 [(E)-3-(4-t-butylphenyl)-N-(2,3-dihydrobenzo[b][1,4] dioxin-6-yl)acrylamide], a novel vanilloid receptor 1 (TRPV1) antagonist with antihyperalgesic properties.
2005 Apr
Anandamide induces necrosis in primary hepatic stellate cells.
2005 May
Further insights into the regulation of human FAAH by progesterone and leptin implications for endogenous levels of anandamide and apoptosis of immune and neuronal cells.
2005 Oct
Fatty acid amide hydrolase deficiency limits early pregnancy events.
2006 Aug
Functional effects of nonsynonymous polymorphisms in the human TRPV1 gene.
2007 Dec
The orphan receptor GPR55 is a novel cannabinoid receptor.
2007 Dec
TRPV1 is a novel target for omega-3 polyunsaturated fatty acids.
2007 Jan 15
Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol.
2007 Mar
Arvanil, anandamide and N-arachidonoyl-dopamine (NADA) inhibit emesis through cannabinoid CB1 and vanilloid TRPV1 receptors in the ferret.
2007 May
Anti-dyskinetic effects of cannabinoids in a rat model of Parkinson's disease: role of CB(1) and TRPV1 receptors.
2007 Nov
Endocannabinoids acting at CB1 receptors mediate the cardiac contractile dysfunction in vivo in cirrhotic rats.
2007 Sep
TRPV2 is activated by cannabidiol and mediates CGRP release in cultured rat dorsal root ganglion neurons.
2008 Jun 11
Direct activation of transient receptor potential vanilloid 1(TRPV1) by diacylglycerol (DAG).
2008 Oct 1
Subunit-specific modulation of glycine receptors by cannabinoids and N-arachidonyl-glycine.
2008 Oct 15
The endocannabinoid anandamide inhibits kinin B1 receptor sensitization through cannabinoid CB1 receptor stimulation in human umbilical vein.
2009 Jan 5
Characterization of anandamide-stimulated cannabinoid receptor signaling in human ULTR myometrial smooth muscle cells.
2009 Sep
Localization and function of cannabinoid receptors in the corpus cavernosum: basis for modulation of nitric oxide synthase nerve activity.
2010 Feb
TRPV1 and TRPA1 stimulation induces MUC5B secretion in the human nasal airway in vivo.
2011 Nov
Δ(9) -Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells.
2012 Apr
Contributions of TRPV1, endovanilloids, and endoplasmic reticulum stress in lung cell death in vitro and lung injury.
2012 Jan 1
Effects of cannabinoids and related fatty acids upon the viability of P19 embryonal carcinoma cells.
2013 Nov
Induction of endocannabinoid levels in juvenile rat brain following developmental chlorpyrifos exposure.
2013 Sep
Enhancement of endocannabinoid signaling protects against cocaine-induced neurotoxicity.
2015 Aug 1
Patents

Sample Use Guides

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 Thu Jul 06 01:29:23 UTC 2023
Edited
by admin
on Thu Jul 06 01:29:23 UTC 2023
Record UNII
UR5G69TJKH
Record Status Validated (UNII)
Record Version
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Name Type Language
ANANDAMIDE
MI  
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
Created by admin on Thu Jul 06 01:29:23 UTC 2023 , Edited by admin on Thu Jul 06 01:29:23 UTC 2023
PRIMARY Merck Index
CHEBI
2700
Created by admin on Thu Jul 06 01:29:23 UTC 2023 , Edited by admin on Thu Jul 06 01:29:23 UTC 2023
PRIMARY
MESH
C078814
Created by admin on Thu Jul 06 01:29:23 UTC 2023 , Edited by admin on Thu Jul 06 01:29:23 UTC 2023
PRIMARY
PUBCHEM
5281969
Created by admin on Thu Jul 06 01:29:23 UTC 2023 , Edited by admin on Thu Jul 06 01:29:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID301017453
Created by admin on Thu Jul 06 01:29:23 UTC 2023 , Edited by admin on Thu Jul 06 01:29:23 UTC 2023
PRIMARY
CAS
94421-68-8
Created by admin on Thu Jul 06 01:29:23 UTC 2023 , Edited by admin on Thu Jul 06 01:29:23 UTC 2023
PRIMARY
WIKIPEDIA
ANANDAMIDE
Created by admin on Thu Jul 06 01:29:23 UTC 2023 , Edited by admin on Thu Jul 06 01:29:23 UTC 2023
PRIMARY
FDA UNII
UR5G69TJKH
Created by admin on Thu Jul 06 01:29:23 UTC 2023 , Edited by admin on Thu Jul 06 01:29:23 UTC 2023
PRIMARY
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