Catalog Number: 1017
Alternate Names: Arachidonylethanolamide, AEA
Chemical Name: N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Biological Activity
Endogenous cannabinoid and vanilloid receptor agonist, in water-soluble emulsion (for details see TocrisolveTM 100, Cat. No. 1684). Ki values are 89 and 371 nM for CB1 and CB2 receptors respectively; EC50 values are 18, 31 and 27 nM at GPR55, CB1 and CB2 respectively; pKi = 5.68 for rVR1. Also blocks TNF-α-induced NF-kB activation via direct inhibition of IKK.

Available as the pure oil dissolved in ethanol, Anandamine. Tocrisolve Control also available.

Technical Data
  • M.Wt:
    347.54
  • Formula:
    C22H37NO2
  • Storage:
    Store at +4°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. Pharmacology of cannabinoid receptor ligands.
    Pertwee
    Curr.Med.Chem., 1999;6:635
  3. 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
  4. Anandamide inhibits nuclear factor-κB activation through a cannabinoid receptor-independent pathway.
    Sancho et al.
    Mol.Pharmacol., 2003;63:429
  5. Complex regional haemodynamic effects of anandamide in conscious rats.
    Gardiner et al.
    Br.J.Pharmacol., 2002;135:1889
  6. Characterization of the anandamide-induced depolarization of guinea-pig isolated vagus nerve.
    Kagaya et al.
    Br.J.Pharmacol., 2002;137:39
Citations:

The citations listed below are publications that use Tocris products. Selected citations for Anandamide (in Tocrisolve™ 100) include:

5 Citations: Showing 1 - 5
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  1. Interaction between anandamide and sphingosine-1-phosphate in mediating vasorelaxation in rat coronary artery.
    Authors: Mair Et al.
    Br J Pharmacol 2010;161:176
  2. Acute hypertension reveals depressor and vasodilator effects of cannabinoids in conscious rats.
    Authors: Ho and Gardiner
    Cereb Cortex 2009;156:94
  3. 'Entourage' effects of N-palmitoylethanolamide and N-oleoylethanolamide on vasorelaxation to anandamide occur through TRPV1 receptors.
    Authors: Ho Et al.
    Br J Pharmacol 2008;155:837
  4. Vanilloid-mediated heterosynaptic facilitation of inhibitory synaptic input to neurons of the rat dorsal motor nucleus of the vagus.
    Authors: Derbenev Et al.
    Cell Death Differ 2006;26:9666
  5. Anandamide-induced cell death in primary neuronal cultures: role of calpain and caspase pathways.
    Authors: Movsesyan Et al.
    Br J Pharmacol 2004;11:1121

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