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.

Available in water soluble emulsion. Deuterated analog also available.

Technical Data
  • M.Wt:
    347.54
  • Formula:
    C22H37NO2
  • Solubility:
    Soluble in ethanol (supplied pre-dissolved in anhydrous ethanol, 5mg/ml)
  • 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. 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.
    Pertwee
    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
Citations:

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

34 Citations: Showing 1 - 10
Filter your results:

  1. 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
  2. AMPK contributes to aerobic exercise-induced antinociception downstream of endocannabinoids.
    Authors: King-Himmelreich
    Neuropharmacology 2017;124:134
  3. Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures.
    Authors: Malek Et al.
    Neural Plast 2015;2015:130639
  4. The Effects of the Endocannabinoids Anandamide and 2-Arachidonoylglycerol on Human Osteoblast Proliferation and Differentiation.
    Authors: Smith Et al.
    PLoS One 2015;10:e0136546
  5. Mechanisms of endothelium-dependent relaxation evoked by anandamide in isolated human pulmonary arteries.
    Authors: Baranowska-Kuczko Et al.
    J Biomed Sci 2014;387:477
  6. 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
  7. CB1 cannabinoid receptors couple to focal adhesion kinase to control insulin release.
    Authors: Malenczyk Et al.
    J Biol Chem 2013;288:32685
  8. Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses.
    Authors: Caiati Et al.
    Sci Rep 2012;2:285
  9. 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
  10. Capsaicin-induced changes in LTP in the lateral amygdala are mediated by TRPV1.
    Authors: Zschenderlein Et al.
    PLoS One 2011;6:e16116
  11. Nigrostriatal denervation changes the effect of cannabinoids on subthalamic neuronal activity in rats.
    Authors: Morera-Herreras Et al.
    Psychopharmacology (Berl) 2011;214:379
  12. 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
  13. 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
  14. Pretreatment with electroacupuncture induces rapid tolerance to focal cerebral ischemia through regulation of endocannabinoid system.
    Authors: Wang Et al.
    Stroke 2009;40:2157
  15. 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
  16. 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 2009;158:1579
  17. Differential endocannabinoid regulation of baroreflex-evoked sympathoinhibition in normotensive versus hypertensive rats.
    Authors: Brozoski Et al.
    Auton Neurosci 2009;150:82
  18. Blockade of THC-seeking behavior and relapse in monkeys by the cannabinoid CB(1)-receptor antagonist rimonabant.
    Authors: Justinova Et al.
    Neuropsychopharmacology 2008;33:2870
  19. 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
  20. 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
  21. TRPV1 as a key determinant in ciguatera and neurotoxic shellfish poisoning.
    Authors: Cuypers Et al.
    Exp Neurol 2007;361:214
  22. 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
  23. 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
  24. 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
  25. 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
  26. Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex.
    Authors: Bender Et al.
    J Neurosci 2006;26:4166
  27. 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
  28. Central and peripheral components of the pressor effect of anandamide in urethane-anaesthetized rats.
    Authors: Kwolek Et al.
    Br J Pharmacol 2005;145:567
  29. 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
  30. Anandamide-induced cell death in primary neuronal cultures: role of calpain and caspase pathways.
    Authors: Movsesyan Et al.
    Br J Pharmacol 2004;11:1121
  31. Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension.
    Authors: Bátkai Et al.
    Eur J Pharmacol 2004;110:1996
  32. '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
  33. Anandamide administration into the ventromedial hypothalamus stimulates appetite in rats.
    Authors: Jamshidi and Taylor
    Br J Pharmacol 2001;134:1151
  34. Differences in the pharmacological properties of rat and chicken brain fatty acid amidohydrolase.
    Authors: Fowler Et al.
    Circulation 2000;131:498
Expand to show all 34 Citations

Have you used Anandamide?

Submit a review and receive a $25US/€18/£15/$25CAN amazon gift card if you include an image - $10US/€7/£6/$10CAN Amazon card for reviews without an image. Limited to verified customers in USA, Canada and Europe.

Tocris Bioscience is the leading supplier of novel and exclusive tools for life science research with over 30 years' experience in the industry. Tocris is a Bio-Techne brand.

Order Details

Note:

Contact Information

Calculators

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

R&D Systems Guarantee

or select another batch: 

Feedback

Customer Information