Catalog Number: 1339
Alternate Names: Arachidonylethanolamide, AEA
Chemical Name: N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Biological Activity
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. Also available in water soluble emulsion (Cat. No. 1017).
Technical Data
  • M.Wt:
  • Formula:
  • Solubility:
    Soluble in ethanol (supplied pre-dissolved in anhydrous ethanol, 5mg/ml)
  • Storage:
    Store at -20°C
  • CAS No:
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis. All Tocris products are intended for laboratory research use only.
Additional Information
Other Product-Specific Information:
Background References
  1. The orphan receptor GPR55 is a novel cannabinoid receptor.
    Ryberg et al.
    Br.J.Pharmacol., 2007;152:1092
  2. Isolation and structure of a brain constituent that binds to the cannabinoid receptor.
    Devane et al.
    Science, 1992;258:1946
  3. Pharmacology of cannabinoid receptor ligands.
    Curr.Med.Chem., 1999;6:635
  4. 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
  5. Anandamide inhibits nuclear factor-κB activation through a cannabinoid receptor-independent pathway.
    Sancho et al.
    Mol.Pharmacol., 2003;63:429

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

Showing Results 1 - 10 of 32

  1. Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures.
    Authors: Malek Et al.
    Neural Plast
  2. The Effects of the Endocannabinoids Anandamide and 2-Arachidonoylglycerol on Human Osteoblast Proliferation and Differentiation.
    Authors: Smith Et al.
    PLoS One
  3. Mechanisms of endothelium-dependent relaxation evoked by anandamide in isolated human pulmonary arteries.
    Authors: Baranowska-Kuczko Et al.
    J Biomed Sci
  4. 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
  5. CB1 cannabinoid receptors couple to focal adhesion kinase to control insulin release.
    Authors: Malenczyk Et al.
    J Biol Chem
  6. Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses.
    Authors: Caiati Et al.
    Sci Rep
  7. 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
  8. Capsaicin-induced changes in LTP in the lateral amygdala are mediated by TRPV1.
    Authors: Zschenderlein Et al.
    PLoS One
  9. Nigrostriatal denervation changes the effect of cannabinoids on subthalamic neuronal activity in rats.
    Authors: Morera-Herreras Et al.
    Psychopharmacology (Berl)
  10. 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
  11. 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
  12. Pretreatment with electroacupuncture induces rapid tolerance to focal cerebral ischemia through regulation of endocannabinoid system.
    Authors: Wang Et al.
  13. Developmental expression of a functional TASK-1 2P domain K+ channel in embryonic chick heart.
    Authors: Zhang Et al.
    Br J Pharmacol
  14. Effect of the CB(1) receptor antagonists rimonabant and AM251 on the firing rate of dorsal raphe nucleus neurons in rat brain slices.
    Authors: Mendiguren and Pineda
    Br J Pharmacol
  15. Differential endocannabinoid regulation of baroreflex-evoked sympathoinhibition in normotensive versus hypertensive rats.
    Authors: Brozoski Et al.
    Auton Neurosci
  16. Blockade of THC-seeking behavior and relapse in monkeys by the cannabinoid CB(1)-receptor antagonist rimonabant.
    Authors: Justinova Et al.
  17. TWIK-related acid-sensitive K+ channel 1 (TASK1) and TASK3 critically influence T lymphocyte effector functions.
    Authors: Meuth Et al.
    J Biol Chem
  18. The differential contractile responses to capsaicin and anandamide in muscle strips isolated from the rat urinary bladder.
    Authors: Saitoh Et al.
    Br J Pharmacol
  19. TRPV1 as a key determinant in ciguatera and neurotoxic shellfish poisoning.
    Authors: Cuypers Et al.
    Exp Neurol
  20. 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
  21. 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
  22. Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol.
    Authors: Ho and Randall
    Naunyn Schmiedebergs Arch Pharmacol
  23. 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
  24. Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex.
    Authors: Bender Et al.
    J Neurosci
  25. Hemodynamic profile, responsiveness to anandamide, and baroreflex sensitivity of mice lacking fatty acid amide hydrolase.
    Authors: Pacher Et al.
    Br J Pharmacol
  26. Central and peripheral components of the pressor effect of anandamide in urethane-anaesthetized rats.
    Authors: Kwolek Et al.
    Br J Pharmacol
  27. Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons.
    Authors: Price Et al.
    Br J Pharmacol
  28. Anandamide-induced cell death in primary neuronal cultures: role of calpain and caspase pathways.
    Authors: Movsesyan Et al.
    Br J Pharmacol
  29. Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension.
    Authors: Bátkai Et al.
    Eur J Pharmacol
  30. '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
  31. Anandamide administration into the ventromedial hypothalamus stimulates appetite in rats.
    Authors: Jamshidi and Taylor
    Br J Pharmacol
  32. Differences in the pharmacological properties of rat and chicken brain fatty acid amidohydrolase.
    Authors: Fowler Et al.
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