U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H37NO2
Molecular Weight 347.5355
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of ANANDAMIDE

SMILES

CCCCC/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\CCCC(=NCCO)O

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 347.5355
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
Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors.
1995 Sep
Anandamide, an endogenous cannabinoid, inhibits Shaker-related voltage-gated K+ channels.
1996
Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands.
1996 Sep
Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat.
1996 Sep 16
Cannabinoid-induced hypotension and bradycardia in rats mediated by CB1-like cannabinoid receptors.
1997 Jun
A comparison of delta 9-THC and anandamide induced c-fos expression in the rat forebrain.
1998 Aug 17
The activity of anandamide at vanilloid VR1 receptors requires facilitated transport across the cell membrane and is limited by intracellular metabolism.
2001 Apr 20
Lipopolysaccharide downregulates fatty acid amide hydrolase expression and increases anandamide levels in human peripheral lymphocytes.
2001 Sep 15
Reduction of human monocytic cell neurotoxicity and cytokine secretion by ligands of the cannabinoid-type CB2 receptor.
2003 Jun
Hypotensive effect of anandamide through the activation of CB1 and VR1 spinal receptors in urethane-anesthetized rats.
2003 Oct
Pharmacological modulation of the endocannabinoid system in a viral model of multiple sclerosis.
2005 Mar
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
A second fatty acid amide hydrolase with variable distribution among placental mammals.
2006 Dec 1
Role of cannabinoid receptor agonists in mechanisms of suppression of central pain syndrome.
2006 Jul
Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents.
2006 Mar
Arvanil and anandamide up-regulate CD36 expression in human peripheral blood mononuclear cells.
2007 Apr 15
A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol.
2007 Dec
TRPV1 is a novel target for omega-3 polyunsaturated fatty acids.
2007 Jan 15
Inhibition of fatty acid amide hydrolase, a key endocannabinoid metabolizing enzyme, by analogues of ibuprofen and indomethacin.
2007 Jun 22
Cannabinoids ameliorate pain and reduce disease pathology in cerulein-induced acute pancreatitis.
2007 May
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
Expression and purification of orphan cytochrome P450 4X1 and oxidation of anandamide.
2008 Jul
TRPV2 is activated by cannabidiol and mediates CGRP release in cultured rat dorsal root ganglion neurons.
2008 Jun 11
Expression of the endocannabinoid system in human first trimester placenta and its role in trophoblast proliferation.
2008 Oct
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
Distribution and function of cannabinoid receptors 1 and 2 in the rat, monkey and human bladder.
2009 Apr
Intermediate cannabis dependence phenotypes and the FAAH C385A variant: an exploratory analysis.
2009 Apr
The endocannabinoid anandamide inhibits kinin B1 receptor sensitization through cannabinoid CB1 receptor stimulation in human umbilical vein.
2009 Jan 5
Fatty acid amide hydrolase (FAAH) inhibition enhances memory acquisition through activation of PPAR-alpha nuclear receptors.
2009 May
Mechanisms of TNFalpha-induced cardiac dysfunction in cholestatic bile duct-ligated mice: interaction between TNFalpha and endocannabinoids.
2010 Aug
Minimal peroxide exposure of neuronal cells induces multifaceted adaptive responses.
2010 Dec 17
Localization and function of cannabinoid receptors in the corpus cavernosum: basis for modulation of nitric oxide synthase nerve activity.
2010 Feb
Alterations of the endocannabinoid system in an animal model of migraine: evaluation in cerebral areas of rat.
2010 Mar
CB1 cannabinoid receptors promote oxidative stress and cell death in murine models of doxorubicin-induced cardiomyopathy and in human cardiomyocytes.
2010 Mar 1
Cyclooxygenase-2 mediates anandamide metabolism in the mouse brain.
2010 Nov
Inhibitors of monoacylglycerol lipase, fatty-acid amide hydrolase and endocannabinoid transport differentially suppress capsaicin-induced behavioral sensitization through peripheral endocannabinoid mechanisms.
2010 Sep
The endogenous cannabinoid anandamide shares discriminative stimulus effects with ∆(9)-tetrahydrocannabinol in fatty acid amide hydrolase knockout mice.
2011 Apr 10
TRPV1 and TRPA1 stimulation induces MUC5B secretion in the human nasal airway in vivo.
2011 Nov
Covalent inhibitors of fatty acid amide hydrolase: a rationale for the activity of piperidine and piperazine aryl ureas.
2011 Oct 13
Δ(9) -Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells.
2012 Apr
Axonal neuropathy-associated TRPV4 regulates neurotrophic factor-derived axonal growth.
2012 Feb 17
Contributions of TRPV1, endovanilloids, and endoplasmic reticulum stress in lung cell death in vitro and lung injury.
2012 Jan 1
Enhancement of endocannabinoid signaling protects against cocaine-induced neurotoxicity.
2015 Aug 1
Decreased anxiety in juvenile rats following exposure to low levels of chlorpyrifos during development.
2017 Mar
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 Sat Jun 26 09:01:42 UTC 2021
Edited
by admin
on Sat Jun 26 09:01:42 UTC 2021
Record UNII
UR5G69TJKH
Record Status Validated (UNII)
Record Version
  • Download
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 Sat Jun 26 09:01:43 UTC 2021 , Edited by admin on Sat Jun 26 09:01:43 UTC 2021
PRIMARY Merck Index
MESH
C078814
Created by admin on Sat Jun 26 09:01:43 UTC 2021 , Edited by admin on Sat Jun 26 09:01:43 UTC 2021
PRIMARY
PUBCHEM
5281969
Created by admin on Sat Jun 26 09:01:43 UTC 2021 , Edited by admin on Sat Jun 26 09:01:43 UTC 2021
PRIMARY
CAS
94421-68-8
Created by admin on Sat Jun 26 09:01:43 UTC 2021 , Edited by admin on Sat Jun 26 09:01:43 UTC 2021
PRIMARY
WIKIPEDIA
ANANDAMIDE
Created by admin on Sat Jun 26 09:01:43 UTC 2021 , Edited by admin on Sat Jun 26 09:01:43 UTC 2021
PRIMARY
FDA UNII
UR5G69TJKH
Created by admin on Sat Jun 26 09:01:43 UTC 2021 , Edited by admin on Sat Jun 26 09:01:43 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
MAJOR