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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
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
Cannabinoid-induced mesenteric vasodilation through an endothelial site distinct from CB1 or CB2 receptors.
1999 Nov 23
Induction of vanilloid receptor channel activity by protein kinase C.
2000 Dec 21-28
The endogenous lipid anandamide is a full agonist at the human vanilloid receptor (hVR1).
2000 Jan
Evidence that 2-arachidonoylglycerol but not N-palmitoylethanolamine or anandamide is the physiological ligand for the cannabinoid CB2 receptor. Comparison of the agonistic activities of various cannabinoid receptor ligands in HL-60 cells.
2000 Jan 7
CB1 cannabinoid receptor-mediated cell migration.
2000 Jul
Cloning and pharmacological characterization of the rat CB(2) cannabinoid receptor.
2000 Mar
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
Purification and characterization of an acid amidase selective for N-palmitoylethanolamine, a putative endogenous anti-inflammatory substance.
2001 Sep 21
Inhibition of methamphetamine self-administration in rats by cannabinoid receptor antagonist AM 251.
2002 Jun
Role of CB1 and CB2 receptors in the inhibitory effects of cannabinoids on lipopolysaccharide-induced nitric oxide release in astrocyte cultures.
2002 Mar 15
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
Hypotensive effect of anandamide through the activation of CB1 and VR1 spinal receptors in urethane-anesthetized rats.
2003 Oct
Arachidonylethanolamide induces apoptosis of human glioma cells through vanilloid receptor-1.
2004 Sep
Cocaine- and amphetamine-related transcript is involved in the orexigenic effect of endogenous anandamide.
2005
The endocannabinoid arachidonyl ethanolamide (anandamide) increases pulmonary arterial pressure via cyclooxygenase-2 products in isolated rabbit lungs.
2005 Dec
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
Mechanisms of HIV-1 inhibition by the lipid mediator N-arachidonoyldopamine.
2005 Sep 15
Effect of topical application of capsaicin and its related compounds on dermal insulin-like growth factor-I levels in mice and on facial skin elasticity in humans.
2007 Apr
A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol.
2007 Dec
Functional effects of nonsynonymous polymorphisms in the human TRPV1 gene.
2007 Dec
Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol.
2007 Mar
Endocannabinoids acting at CB1 receptors mediate the cardiac contractile dysfunction in vivo in cirrhotic rats.
2007 Sep
Expression of the endocannabinoid system in human first trimester placenta and its role in trophoblast proliferation.
2008 Oct
Subunit-specific modulation of glycine receptors by cannabinoids and N-arachidonyl-glycine.
2008 Oct 15
Fatty acid amide hydrolase (FAAH) inhibition enhances memory acquisition through activation of PPAR-alpha nuclear receptors.
2009 May
Localization and function of cannabinoid receptors in the corpus cavernosum: basis for modulation of nitric oxide synthase nerve activity.
2010 Feb
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
Δ(9) -Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells.
2012 Apr
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
Contrasting protective effects of cannabinoids against oxidative stress and amyloid-β evoked neurotoxicity in vitro.
2012 Jan
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
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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 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