Home / Non-selective Cannabinoid Receptor Agonists / Anandamide

Anandamide

Catalog #: 1339
48 Citations Datasheet
Catalog # Availability Size / Price Qty
1339/25
1339/5
Anandamide | CAS No. 94421-68-8 | Non-selective Cannabinoid Receptor Agonists
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Description: Endogenous and non-selective CB agonist
Alternative Names: Arachidonylethanolamide,AEA

Chemical Name: N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide

Purity: ≥98%

Product Details
Citations (48)
Supplemental Products
Reviews
Biological Activity Technical Data Additional Information Background Product Datasheets Calculators

Biological Activity

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

M.Wt:
347.54
Formula:
C22H37NO2
Solubility:
Soluble in ethanol (supplied pre-dissolved in anhydrous ethanol, 5mg/ml)
Purity:
≥98%
Storage:
Store at -20°C
CAS No:
94421-68-8

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.

Additional Information

Other Product-Specific Information:

Background References

  1. Inhibition of fatty acid binding proteins elevates brain anandamide levels and produces analgesia.
    Kaczocha M, Rebecchi M, Ralph B, Teng Y, Berger W, Galbavy W, Elmes M, Glaser S, Wang L, Rizzo R, Deutsch D, Ojima I
    PLoS ONE, 2014;9(4):e94200.
  2. The endocannabinoid/endovanilloid N-arachidonoyl dopamine (NADA) and synthetic cannabinoid WIN55,212-2 abate the inflammatory activation of human endothelial cells.
    Wilhelmsen K, Khakpour S, Tran A, Sheehan K, Schumacher M, Xu F, Hellman J
    J Biol Chem, 2014;289(19):13079-100.
  3. The endocannabinoid anandamide induces apoptosis in cytotrophoblast cells: involvement of both mitochondrial and death receptor pathways.
    Costa M, Fonseca B, Teixeira N, Correia-da-Silva G
    Placenta, 2014;36(1):69-76.
  4. Pharmacology of cannabinoid receptor ligands.
    Pertwee
    Curr.Med.Chem., 1999;6:635
  5. The orphan receptor GPR55 is a novel cannabinoid receptor.
    Ryberg et al.
    Br.J.Pharmacol., 2007;152:1092
  6. Isolation and structure of a brain constituent that binds to the cannabinoid receptor.
    Devane et al.
    Science, 1992;258:1946
  7. Anandamide inhibits nuclear factor-κB activation through a cannabinoid receptor-independent pathway.
    Sancho et al.
    Mol.Pharmacol., 2003;63:429
  8. 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.
    Br.J.Pharmacol., 2001;132:631
  9. Endocannabinoids inhibit the induction of virulence in enteric pathogens.
    Ellermann et al.
    Cell, 2020;

Product Datasheets

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Citations for Anandamide

The citations listed below are publications that use Tocris products. Selected citations for Anandamide include:

48 Citations: Showing 1 - 10

  1. Endocannabinoids inhibit the induction of virulence in enteric pathogens.
    Authors: Ellermann Et al.
    Cell  2020;183:650
  2. 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
  3. The synthetic cannabinoid WIN-55,212-55,212 induced-apoptosis in cytotrophoblasts cells by a mechanism dependent on CB1 receptor.
    Authors: Almada
    Toxicology  2017;385:67
  4. AMPK contributes to aerobic exercise-induced antinociception downstream of endocannabinoids.
    Authors: King-Himmelreich
    Neuropharmacology  2017;124:134
  5. 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
  6. Regulation of divalent metal transporter-1 by serine phosphorylation.
    Authors: Seo Et al.
    Biochem J  2016;473:4243
  7. Behavioral Characterization of the Effects of Cannabis Smoke and Anandamide in Rats.
    Authors: Bruijnzeel Et al.
    PLoS One  2016;11:e0153327
  8. Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures.
    Authors: Malek Et al.
    Neural Plast  2015;2015:130639
  9. The Effects of the Endocannabinoids Anandamide and 2-Arachidonoylglycerol on Human Osteoblast Proliferation and Differentiation.
    Authors: Smith Et al.
    PLoS One  2015;10:e0136546
  10. Mechanisms of endothelium-dependent relaxation evoked by anandamide in isolated human pulmonary arteries.
    Authors: Baranowska-Kuczko Et al.
    J Biomed Sci  2014;387:477
  11. 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
  12. 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
  13. CB1 cannabinoid receptors couple to focal adhesion kinase to control Ins release.
    Authors: Malenczyk Et al.
    J Biol Chem  2013;288:32685
  14. Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses.
    Authors: Caiati Et al.
    Sci Rep  2012;2:285
  15. 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
  16. Capsaicin-induced changes in LTP in the lateral amygdala are mediated by TRPV1.
    Authors: Zschenderlein Et al.
    PLoS One  2011;6:e16116
  17. Nigrostriatal denervation changes the effect of cannabinoids on subthalamic neuronal activity in rats.
    Authors: Morera-Herreras Et al.
    Psychopharmacology (Berl)  2011;214:379
  18. 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
  19. 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
  20. Pretreatment with electroacupuncture induces rapid tolerance to focal cerebral ischemia through regulation of endocannabinoid system.
    Authors: Wang Et al.
    Stroke  2009;40:2157
  21. 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
  22. 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
  23. Differential endocannabinoid regulation of baroreflex-evoked sympathoinhibition in normotensive versus hypertensive rats.
    Authors: Brozoski Et al.
    Auton Neurosci  2009;150:82
  24. Human keratinocytes are vanilloid resistant.
    Authors: Pecze Et al.
    PLoS One  2008;3:e3419
  25. Blockade of THC-seeking behavior and relapse in monkeys by the cannabinoid CB(1)-receptor antagonist rimon.
    Authors: Justinova Et al.
    Neuropsychopharmacology  2008;33:2870
  26. 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
  27. 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
  28. TRPV1 as a key determinant in ciguatera and neurotoxic shellfish poisoning.
    Authors: Cuypers Et al.
    Exp Neurol  2007;361:214
  29. 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
  30. Characterization of the vasorelaxant mechanisms of the endocannabinoid anandamide in rat aorta.
    Authors: Herradón Et al.
    Br J Pharmacol  2007;152:699
  31. 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
  32. 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
  33. 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
  34. Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex.
    Authors: Bender Et al.
    J Neurosci  2006;26:4166
  35. Modulation of P-glycoprotein activity by cannabinoid molecules in HK-2 renal cells.
    Authors: Nieri Et al.
    Br J Pharmacol  2006;148:682
  36. 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
  37. The wake-promoting peptide orexin-B inhibits glutamatergic transmission to dorsal raphe nucleus serotonin neurons through retrograde endocannabinoid signaling.
    Authors: Haj-Dahmane
    J Neurosci  2005;25:896
  38. Extracellular cations sensitize and gate capsaicin receptor TRPV1 modulating pain signaling.
    Authors: Ahern Et al.
    J Neurosci  2005;25:5109
  39. Central and peripheral components of the pressor effect of anandamide in urethane-anaesthetized rats.
    Authors: Kwolek Et al.
    Br J Pharmacol  2005;145:567
  40. 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
  41. 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
  42. Anandamide-induced cell death in primary neuronal cultures: role of calpain and caspase pathways.
    Authors: Movsesyan Et al.
    Br J Pharmacol  2004;11:1121
  43. Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension.
    Authors: Bátkai Et al.
    Eur J Pharmacol  2004;110:1996
  44. '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
  45. 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
  46. Anandamide administration into the ventromedial hypothalamus stimulates appetite in rats.
    Authors: Jamshidi and Taylor
    Br J Pharmacol  2001;134:1151
  47. Effect of vanilloid drugs on gastrointestinal transit in mice.
    Authors: Izzo Et al.
    Br J Pharmacol  2001;132:1411
  48. Differences in the pharmacological properties of rat and chicken brain fatty acid amidohydrolase.
    Authors: Fowler Et al.
    Circulation  2000;131:498

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