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
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-
| 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).
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Molecular characterization of a peripheral receptor for cannabinoids. | 1993 Sep 2 |
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| Anandamide, an endogenous cannabinoid, inhibits Shaker-related voltage-gated K+ channels. | 1996 |
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| Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands. | 1996 Sep |
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| Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat. | 1996 Sep 16 |
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| Cannabinoid-induced hypotension and bradycardia in rats mediated by CB1-like cannabinoid receptors. | 1997 Jun |
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| A comparison of delta 9-THC and anandamide induced c-fos expression in the rat forebrain. | 1998 Aug 17 |
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| Fatty acid amide hydrolase deficiency limits early pregnancy events. | 2006 Aug |
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| A second fatty acid amide hydrolase with variable distribution among placental mammals. | 2006 Dec 1 |
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| Role of cannabinoid receptor agonists in mechanisms of suppression of central pain syndrome. | 2006 Jul |
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| 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 |
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| Arvanil and anandamide up-regulate CD36 expression in human peripheral blood mononuclear cells. | 2007 Apr 15 |
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| A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol. | 2007 Dec |
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| Functional effects of nonsynonymous polymorphisms in the human TRPV1 gene. | 2007 Dec |
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| The orphan receptor GPR55 is a novel cannabinoid receptor. | 2007 Dec |
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| 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 |
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| Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol. | 2007 Mar |
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| 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 |
|
| Cannabinoid activation of PPAR alpha; a novel neuroprotective mechanism. | 2007 Nov |
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| 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 |
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| Expression and purification of orphan cytochrome P450 4X1 and oxidation of anandamide. | 2008 Jul |
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| 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 |
|
| Characterization of anandamide-stimulated cannabinoid receptor signaling in human ULTR myometrial smooth muscle cells. | 2009 Sep |
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| 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 |
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| 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 |
|
| 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 |
|
| Axonal neuropathy-associated TRPV4 regulates neurotrophic factor-derived axonal growth. | 2012 Feb 17 |
|
| Contrasting protective effects of cannabinoids against oxidative stress and amyloid-β evoked neurotoxicity in vitro. | 2012 Jan |
|
| Contributions of TRPV1, endovanilloids, and endoplasmic reticulum stress in lung cell death in vitro and lung injury. | 2012 Jan 1 |
|
| Induction of endocannabinoid levels in juvenile rat brain following developmental chlorpyrifos exposure. | 2013 Sep |
|
| 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
Fri Dec 15 18:14:18 GMT 2023
by
admin
on
Fri Dec 15 18:14:18 GMT 2023
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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
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2700
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C078814
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DTXSID301017453
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94421-68-8
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ANANDAMIDE
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UR5G69TJKH
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| Related Record | Type | Details | ||
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TARGET -> AGONIST |
Natural agonist
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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ACTIVATOR -> TARGET |
Inhibits reuptake
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TARGET -> AGONIST |
IC50
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TARGET -> SUBSTRATE |
MAJOR
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| Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
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