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Submit ReviewAnandamide (in Tocrisolve™ 100)
Description: Endogenous CB receptor agonist (in water-soluble emulsion)
Alternative Names: Arachidonylethanolamide,AEA
Chemical Name: N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Biological Activity for Anandamide (in Tocrisolve™ 100)
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 for Anandamide (in Tocrisolve™ 100)
| M. Wt | 347.54 |
| Formula | C22H37NO2 |
| Storage | Store at +4°C |
| 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.
Product Datasheets for Anandamide (in Tocrisolve™ 100)
References for Anandamide (in Tocrisolve™ 100)
References are publications that support the biological activity of the product.
Gardiner et al (2002) Complex regional haemodynamic effects of anandamide in conscious rats. Br.J.Pharmacol. 135 1889 PMID: 11959791
Kagaya et al (2002) Characterization of the anandamide-induced depolarization of guinea-pig isolated vagus nerve. Br.J.Pharmacol. 137 39 PMID: 12183329
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
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Keywords: Anandamide (in Tocrisolve 100), Anandamide (in Tocrisolve 100) supplier, Endogenous, CB, agonist, water-soluble, emulsion, vanilloid, Cannabinoids, Non-Selective, Receptors, Vanillioid, VR1, TRPV, TRP, Channels, Transient, Receptor, Potential, cb2r, cb1r, Arachidonylethanolamide, AEA, Non-selective, 1017, Tocris Bioscience
6 Citations for Anandamide (in Tocrisolve™ 100)
Citations are publications that use Tocris products. Selected citations for Anandamide (in Tocrisolve™ 100) include:
Mair et al (2010) Interaction between anandamide and sphingosine-1-phosphate in mediating vasorelaxation in rat coronary artery. Br J Pharmacol 161 176 PMID: 20718749
Derbenev et al (2006) Vanilloid-mediated heterosynaptic facilitation of inhibitory synaptic input to neurons of the rat dorsal motor nucleus of the vagus. Cell Death Differ 26 9666 PMID: 16988037
Diniz et al (2019) Dual mechanism of TRKB activation by anandamide through CB1 and TRPV1 receptors. PeerJ 7 e6493 PMID: 30809460
Ho et al (2008) 'Entourage' effects of N-palmitoylethanolamide and N-oleoylethanolamide on vasorelaxation to anandamide occur through TRPV1 receptors. Br J Pharmacol 155 837 PMID: 18695637
Ho and Gardiner (2009) Acute hypertension reveals depressor and vasodilator effects of cannabinoids in conscious rats. Cereb Cortex 156 94 PMID: 19133994
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
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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.