Chemical Name: N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Biological ActivityEndogenous cannabinoid and TRPV1 receptor agonist (Ki values are 89 and 371 nM at CB1 and CB2 receptors respectively; EC50 values are 18, 31 and 27 nM at GPR55, CB1 and CB2 respectively; pKi = 5.68 for rTRPV1). Also blocks TNF-α-induced NF-κB activation via direct inhibition of IKK.
Deuterated analog also available.
The technical data provided above is for guidance only.
For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Pharmacology of cannabinoid receptor ligands.
The orphan receptor GPR55 is a novel cannabinoid receptor.
Ryberg et al.
Isolation and structure of a brain constituent that binds to the cannabinoid receptor.
Devane et al.
Anandamide inhibits nuclear factor-κB activation through a cannabinoid receptor-independent pathway.
Sancho et al.
Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens.
Ross et al.
Citations for Anandamide
The citations listed below are publications that use Tocris products. Selected citations for Anandamide include:
48 Citations: Showing 1 - 10
Endocannabinoids inhibit the induction of virulence in enteric pathogens.
Authors: Ellermann Et al.
CB1 receptor activation induces intracellular Ca2+ mobilization and 2-arachidonoylglycerol release in rodent spinal cord astrocytes.
Authors: Hegyi Et al.
Sci Rep 2018;8:10562
The synthetic cannabinoid WIN-55,212-55,212 induced-apoptosis in cytotrophoblasts cells by a mechanism dependent on CB1 receptor.
AMPK contributes to aerobic exercise-induced antinociception downstream of endocannabinoids.
Spatial Distribution of the Cannabinoid Type 1 and Capsaicin Receptors May Contribute to the Complexity of Their Crosstalk.
Authors: Chen Et al.
Sci Rep 2016;6:33307
Regulation of divalent metal transporter-1 by serine phosphorylation.
Authors: Seo Et al.
Biochem J 2016;473:4243
Behavioral Characterization of the Effects of Cannabis Smoke and Anandamide in Rats.
Authors: Bruijnzeel Et al.
PLoS One 2016;11:e0153327
Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures.
Authors: Malek Et al.
Neural Plast 2015;2015:130639
The Effects of the Endocannabinoids Anandamide and 2-Arachidonoylglycerol on Human Osteoblast Proliferation and Differentiation.
Authors: Smith Et al.
PLoS One 2015;10:e0136546
Mechanisms of endothelium-dependent relaxation evoked by anandamide in isolated human pulmonary arteries.
Authors: Baranowska-Kuczko Et al.
J Biomed Sci 2014;387:477
The inhibition of 2-arachidonoyl-glycerol (2-AG) biosynthesis, rather than enhancing striatal damage, protects striatal neurons from malonate-induced death: a potential role of cyclooxygenase-2-dependent metabolism of 2-AG.
Authors: Valdeolivas Et al.
Cell Death Dis 2013;4:e862
Endocannabinoids in the brainstem modulate dural trigeminovascular nociceptive traffic via CB1 and "triptan" receptors: implications in migraine.
Authors: Akerman Et al.
J Neurosci 2013;33:14869
CB1 cannabinoid receptors couple to focal adhesion kinase to control Ins release.
Authors: Malenczyk Et al.
J Biol Chem 2013;288:32685
Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses.
Authors: Caiati Et al.
Sci Rep 2012;2:285
Lack of effect of chronic pre-treatment with the FAAH inhibitor URB597 on inflammatory pain behaviour: evidence for plastic changes in the endocannabinoid system.
Authors: Okine Et al.
Am J Physiol Heart Circ Physiol 2012;167:627
Capsaicin-induced changes in LTP in the lateral amygdala are mediated by TRPV1.
Authors: Zschenderlein Et al.
PLoS One 2011;6:e16116
Nigrostriatal denervation changes the effect of cannabinoids on subthalamic neuronal activity in rats.
Authors: Morera-Herreras Et al.
Psychopharmacology (Berl) 2011;214:379
Effects of TRPV1 activation on synaptic excitation in the dentate gyrus of a mouse model of temporal lobe epilepsy.
Authors: Bhaskaran and Smith
Cell Death Differ 2010;223:529
Cannabinoid-1 receptor activation induces reactive oxygen species-dependent and -independent mitogen-activated protein kinase activation and cell death in human coronary artery endothelial cells.
Authors: Rajesh Et al.
Br J Pharmacol 2010;160:688
Pretreatment with electroacupuncture induces rapid tolerance to focal cerebral ischemia through regulation of endocannabinoid system.
Authors: Wang Et al.
Developmental expression of a functional TASK-1 2P domain K+ channel in embryonic chick heart.
Authors: Zhang Et al.
Br J Pharmacol 2009;16:104
Effect of the CB(1) receptor antagonists rimon. and AM251 on the firing rate of dorsal raphe nucleus neurons in rat brain slices.
Authors: Mendiguren and Pineda
Br J Pharmacol 2009;158:1579
Differential endocannabinoid regulation of baroreflex-evoked sympathoinhibition in normotensive versus hypertensive rats.
Authors: Brozoski Et al.
Auton Neurosci 2009;150:82
Human keratinocytes are vanilloid resistant.
Authors: Pecze Et al.
PLoS One 2008;3:e3419
Blockade of THC-seeking behavior and relapse in monkeys by the cannabinoid CB(1)-receptor antagonist rimon.
Authors: Justinova Et al.
TWIK-related acid-sensitive K+ channel 1 (TASK1) and TASK3 critically influence T lymphocyte effector functions.
Authors: Meuth Et al.
J Biol Chem 2008;283:14559
The differential contractile responses to capsaicin and anandamide in muscle strips isolated from the rat urinary bladder.
Authors: Saitoh Et al.
Br J Pharmacol 2007;570:182
TRPV1 as a key determinant in ciguatera and neurotoxic shellfish poisoning.
Authors: Cuypers Et al.
Exp Neurol 2007;361:214
Decreased age-related cardiac dysfunction, myocardial nitrative stress, inflammatory gene expression, and apoptosis in mice lacking fatty acid amide hydrolase.
Authors: Bátkai Et al.
Am J Physiol Heart Circ Physiol 2007;293:H909
Characterization of the vasorelaxant mechanisms of the endocannabinoid anandamide in rat aorta.
Authors: Herradón Et al.
Br J Pharmacol 2007;152:699
Inhibition of 2-arachidonoylglycerol catabolism modulates vasoconstriction of rat middle cerebral artery by the thromboxane mimetic, U-46619.
Authors: Hillard Et al.
Br J Pharmacol 2007;152:691
Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol.
Authors: Ho and Randall
Naunyn Schmiedebergs Arch Pharmacol 2007;150:641
Alkylamides from Echinacea are a new class of cannabinomimetics. Cannabinoid type 2 receptor-dependent and -independent immunomodulatory effects.
Authors: Raduner Et al.
J Biol Chem 2006;281:14192
Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex.
Authors: Bender Et al.
J Neurosci 2006;26:4166
Modulation of P-glycoprotein activity by cannabinoid molecules in HK-2 renal cells.
Authors: Nieri Et al.
Br J Pharmacol 2006;148:682
Hemodynamic profile, responsiveness to anandamide, and baroreflex sensitivity of mice lacking fatty acid amide hydrolase.
Authors: Pacher Et al.
Br J Pharmacol 2005;289:H533
The wake-promoting peptide orexin-B inhibits glutamatergic transmission to dorsal raphe nucleus serotonin neurons through retrograde endocannabinoid signaling.
J Neurosci 2005;25:896
Extracellular cations sensitize and gate capsaicin receptor TRPV1 modulating pain signaling.
Authors: Ahern Et al.
J Neurosci 2005;25:5109
Central and peripheral components of the pressor effect of anandamide in urethane-anaesthetized rats.
Authors: Kwolek Et al.
Br J Pharmacol 2005;145:567
Disruption of endocannabinoid release and striatal long-term depression by postsynaptic blockade of endocannabinoid membrane transport.
Authors: Ronesi Et al.
J Neurosci 2004;24:1673
Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons.
Authors: Price Et al.
Br J Pharmacol 2004;142:257
Anandamide-induced cell death in primary neuronal cultures: role of calpain and caspase pathways.
Authors: Movsesyan Et al.
Br J Pharmacol 2004;11:1121
Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension.
Authors: Bátkai Et al.
Eur J Pharmacol 2004;110:1996
'Entourage' effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism.
Authors: Smart Et al.
J Biomol Screen 2002;136:452
The endocannabinoid anandamide is a direct and selective blocker of the background K(+) channel TASK-1.
Authors: Maingret Et al.
EMBO J 2001;20:47
Anandamide administration into the ventromedial hypothalamus stimulates appetite in rats.
Authors: Jamshidi and Taylor
Br J Pharmacol 2001;134:1151
Effect of vanilloid drugs on gastrointestinal transit in mice.
Authors: Izzo Et al.
Br J Pharmacol 2001;132:1411
Differences in the pharmacological properties of rat and chicken brain fatty acid amidohydrolase.
Authors: Fowler Et al.
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Performed an exposure using different concentrations of anandamide. Didn't have any issues diluting it.