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Submit ReviewAnandamide
Description: Endogenous and non-selective CB agonist
Alternative Names: Arachidonylethanolamide,AEA
Chemical Name: N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Purity: ≥98% (HPLC)
Biological Activity for Anandamide
Anandamide is an endogenous 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.
Technical Data for Anandamide
| M. Wt | 347.54 |
| Formula | C22H37NO2 |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 94421-68-8 |
| PubChem ID | 5281969 |
| InChI Key | LGEQQWMQCRIYKG-DOFZRALJSA-N |
| Smiles | O=C(NCCO)CCC\C=C/C\C=C/C/C=C\C/C=C\CCCCC |
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.
Solubility Data for Anandamide
| Solubility | Soluble in ethanol (supplied pre-dissolved in anhydrous ethanol, 5mg/ml) |
Product Datasheets for Anandamide
References for Anandamide
References are publications that support the biological activity of the product.
Devane et al (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258 1946 PMID: 1470919
Pertwee (1999) Pharmacology of cannabinoid receptor ligands. Curr.Med.Chem. 6 635 PMID: 10469884
Ross et al (2001) Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens. Br.J.Pharmacol. 132 631 PMID: 11159715
Ryberg et al (2007) The orphan receptor GPR55 is a novel cannabinoid receptor. Br.J.Pharmacol. 152 1092 PMID: 17876302
Sancho et al (2003) Anandamide inhibits nuclear factor-κB activation through a cannabinoid receptor-independent pathway. Mol.Pharmacol. 63 429 PMID: 12527815
Ellermann et al (2020) Endocannabinoids inhibit the induction of virulence in enteric pathogens. Cell 183 650 PMID: 33031742
If you know of a relevant reference for Anandamide, please let us know.
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Keywords: Anandamide, Anandamide supplier, Endogenous, CB, receptor, agonists, vanilloids, cannabinoids, Non-Selective, Receptors, VR1, TRPV, Channels, Transient, Receptor, Potential, cb2r, cb1r, endocannabinoids, AEA, Arachidonylethanolamide, Non-selective, Cannabinoids, 1339, Tocris Bioscience
48 Citations for Anandamide
Citations are publications that use Tocris products. Selected citations for Anandamide include:
Bhaskaran and Smith (2010) Effects of TRPV1 activation on synaptic excitation in the dentate gyrus of a mouse model of temporal lobe epilepsy. Cell Death Differ 223 529 PMID: 20144892
Akerman et al (2013) Endocannabinoids in the brainstem modulate dural trigeminovascular nociceptive traffic via CB1 and "triptan" receptors: implications in migraine. J Neurosci 33 14869 PMID: 24027286
Caiati et al (2012) Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses. Sci Rep 2 285 PMID: 22368777
Seo et al (2016) Regulation of divalent metal transporter-1 by serine phosphorylation. Biochem J 473 4243 PMID: 27681840
Chen et al (2016) Spatial Distribution of the Cannabinoid Type 1 and Capsaicin Receptors May Contribute to the Complexity of Their Crosstalk. Sci Rep 6 33307 PMID: 27653550
Bruijnzeel et al (2016) Behavioral Characterization of the Effects of Cannabis Smoke and Anandamide in Rats. PLoS One 11 e0153327 PMID: 27065006
Okine et al (2012) Lack of effect of chronic pre-treatment with the FAAH inhibitor URB597 on inflammatory pain behaviour: evidence for plastic changes in the endocannabinoid system. Am J Physiol Heart Circ Physiol 167 627 PMID: 22595021
Rajesh et al (2010) 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. Br J Pharmacol 160 688 PMID: 20590572
Hegyi et al (2018) CB1 receptor activation induces intracellular Ca2+ mobilization and 2-arachidonoylglycerol release in rodent spinal cord astrocytes. Sci Rep 8 10562 PMID: 30002493
Smith et al (2015) The Effects of the Endocannabinoids Anandamide and 2-Arachidonoylglycerol on Human Osteoblast Proliferation and Differentiation. PLoS One 10 e0136546 PMID: 26414859
Malek et al (2015) Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures. Neural Plast 2015 130639 PMID: 26090232
Ellermann et al (2020) Endocannabinoids inhibit the induction of virulence in enteric pathogens. Cell 183 650 PMID: 33031742
Morera-Herreras et al (2011) Nigrostriatal denervation changes the effect of cannabinoids on subthalamic neuronal activity in rats. Psychopharmacology (Berl) 214 379 PMID: 20959968
Zschenderlein et al (2011) Capsaicin-induced changes in LTP in the lateral amygdala are mediated by TRPV1. PLoS One 6 e16116 PMID: 21249195
Baranowska-Kuczko et al (2014) Mechanisms of endothelium-dependent relaxation evoked by anandamide in isolated human pulmonary arteries. J Biomed Sci 387 477 PMID: 24682422
Valdeolivas et al (2013) 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. Cell Death Dis 4 e862 PMID: 24136226
Malenczyk et al (2013) CB1 cannabinoid receptors couple to focal adhesion kinase to control Ins release. J Biol Chem 288 32685 PMID: 24089517
Zhang et al (2009) Developmental expression of a functional TASK-1 2P domain K+ channel in embryonic chick heart. Br J Pharmacol 16 104 PMID: 19930646
Almada (2017) The synthetic cannabinoid WIN-55,212-55,212 induced-apoptosis in cytotrophoblasts cells by a mechanism dependent on CB1 receptor. Toxicology 385 67 PMID: 28495606
King-Himmelreich (2017) AMPK contributes to aerobic exercise-induced antinociception downstream of endocannabinoids. Neuropharmacology 124 134 PMID: 28479394
Raduner et al (2006) Alkylamides from Echinacea are a new class of cannabinomimetics. Cannabinoid type 2 receptor-dependent and -independent immunomodulatory effects. J Biol Chem 281 14192 PMID: 16547349
Bender et al (2006) Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex. J Neurosci 26 4166 PMID: 16624937
Nieri et al (2006) Modulation of P-glycoprotein activity by cannabinoid molecules in HK-2 renal cells. Br J Pharmacol 148 682 PMID: 16715117
Haj-Dahmane (2005) The wake-promoting peptide orexin-B inhibits glutamatergic transmission to dorsal raphe nucleus serotonin neurons through retrograde endocannabinoid signaling. J Neurosci 25 896 PMID: 15673670
Ahern et al (2005) Extracellular cations sensitize and gate capsaicin receptor TRPV1 modulating pain signaling. J Neurosci 25 5109 PMID: 15917451
Saitoh et al (2007) The differential contractile responses to capsaicin and anandamide in muscle strips isolated from the rat urinary bladder. Br J Pharmacol 570 182 PMID: 17586490
Cuypers et al (2007) TRPV1 as a key determinant in ciguatera and neurotoxic shellfish poisoning. Exp Neurol 361 214 PMID: 17659256
Pecze et al (2008) Human keratinocytes are vanilloid resistant. PLoS One 3 e3419 PMID: 18852901
Herradón et al (2007) Characterization of the vasorelaxant mechanisms of the endocannabinoid anandamide in rat aorta. Br J Pharmacol 152 699 PMID: 17704831
Ho and Randall (2007) Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol. Naunyn Schmiedebergs Arch Pharmacol 150 641 PMID: 17245358
Hillard et al (2007) Inhibition of 2-arachidonoylglycerol catabolism modulates vasoconstriction of rat middle cerebral artery by the thromboxane mimetic, U-46619. Br J Pharmacol 152 691 PMID: 17891162
Bátkai et al (2007) Decreased age-related cardiac dysfunction, myocardial nitrative stress, inflammatory gene expression, and apoptosis in mice lacking fatty acid amide hydrolase. Am J Physiol Heart Circ Physiol 293 H909 PMID: 17434980
Justinova et al (2008) Blockade of THC-seeking behavior and relapse in monkeys by the cannabinoid CB(1)-receptor antagonist rimon. Neuropsychopharmacology 33 2870 PMID: 18305459
Meuth et al (2008) TWIK-related acid-sensitive K+ channel 1 (TASK1) and TASK3 critically influence T lymphocyte effector functions. J Biol Chem 283 14559 PMID: 18375952
Izzo et al (2001) Effect of vanilloid drugs on gastrointestinal transit in mice. Br J Pharmacol 132 1411 PMID: 11264233
Maingret et al (2001) The endocannabinoid anandamide is a direct and selective blocker of the background K(+) channel TASK-1. EMBO J 20 47 PMID: 11226154
Jamshidi and Taylor (2001) Anandamide administration into the ventromedial hypothalamus stimulates appetite in rats. Br J Pharmacol 134 1151 PMID: 11704633
Fowler et al (2000) Differences in the pharmacological properties of rat and chicken brain fatty acid amidohydrolase. Circulation 131 498 PMID: 11015300
Price et al (2004) Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons. Br J Pharmacol 142 257 PMID: 15155534
Ronesi et al (2004) Disruption of endocannabinoid release and striatal long-term depression by postsynaptic blockade of endocannabinoid membrane transport. J Neurosci 24 1673 PMID: 14973237
Smart et al (2002) 'Entourage' effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism. J Biomol Screen 136 452 PMID: 12023948
Brozoski et al (2009) Differential endocannabinoid regulation of baroreflex-evoked sympathoinhibition in normotensive versus hypertensive rats. Auton Neurosci 150 82 PMID: 19464961
Mendiguren and Pineda (2009) Effect of the CB(1) receptor antagonists rimon. and AM251 on the firing rate of dorsal raphe nucleus neurons in rat brain slices. Br J Pharmacol 158 1579 PMID: 19845674
Wang et al (2009) Pretreatment with electroacupuncture induces rapid tolerance to focal cerebral ischemia through regulation of endocannabinoid system. Stroke 40 2157 PMID: 19372445
Kwolek et al (2005) Central and peripheral components of the pressor effect of anandamide in urethane-anaesthetized rats. Br J Pharmacol 145 567 PMID: 15834445
Pacher et al (2005) Hemodynamic profile, responsiveness to anandamide, and baroreflex sensitivity of mice lacking fatty acid amide hydrolase. Br J Pharmacol 289 H533 PMID: 15821037
Movsesyan et al (2004) Anandamide-induced cell death in primary neuronal cultures: role of calpain and caspase pathways. Br J Pharmacol 11 1121 PMID: 15375383
Bátkai et al (2004) Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension. Eur J Pharmacol 110 1996 PMID: 15451779
Do you know of a great paper that uses Anandamide from Tocris? Please let us know.
Reviews for Anandamide
Average Rating: 4.5 (Based on 2 Reviews.)
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Works well for bacterial assays.
By
Kevin Lorch on 10/05/2022
Assay Type: In Vivo
Species: Other
Used in a bacterial signaling assay to screen for potential sensors of anandamide. Very easy to work with, non-toxic to E. coli even at concentrations up to 1 mg/mL. Planning to reorder for some follow-up experiments. Only downside is having to store at -80C.
test.
By
Anonymous on 08/10/2020
Species: Human
Performed an exposure using different concentrations of anandamide. Didn't have any issues diluting it.
Diluted it in ethanol and kept it at -20 C until needed to use.
Literature in this Area
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Cannabinoid Receptor Ligands Scientific Review
Written by Roger Pertwee, this review discusses compounds which affect the activity of the endocannabinoid system, focusing particularly on ligands that are most widely used as experimental tools and denotes compounds available from Tocris.