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
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-
| 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).
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
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| 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 |
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| 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 |
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
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
Edited
Sat Jun 26 09:01:42 UTC 2021
by
admin
on
Sat Jun 26 09:01:42 UTC 2021
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| Record UNII |
UR5G69TJKH
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| Record Status |
Validated (UNII)
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| Record Version |
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M1888
Created by
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C078814
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5281969
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94421-68-8
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admin on Sat Jun 26 09:01:43 UTC 2021 , Edited by admin on Sat Jun 26 09:01:43 UTC 2021
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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
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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
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