ACEA

Cat. No. 1319

ACEA C22H36ClNO [220556-69-4]

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Alternative Name: Arachidonyl-2'-chloroethylamide

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

Biological Activity

Potent and highly selective CB1 receptor agonist (Ki = 1.4 nM). Displays >1400-fold selectivity over CB2 receptors. Active in vivo.

Technical Data

M.Wt:
365.99
Formula:
C22H36ClNO
Solubility:
Soluble in ethanol (supplied pre-dissolved in anhydrous ethanol, 5mg/ml)
Storage:
Store at -20°C
CAS No:
220556-69-4

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.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

Certificate of Analysis / Product Datasheet
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Patel et al (2001) Cannabinoid CB1 receptor agonists produce cerebellar dysfunction in mice. J.Pharmacol.Exp.Ther. 297 629. PMID: 11303052 .

Hillard et al (1999) Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1). J.Pharmacol.Exp.Ther. 289 1427. PMID: 10336536.

Pertwee (1999) Pharmacology of cannabinoid receptor ligands. Curr.Med.Chem. 6 635. PMID: 10469884.

If you know of a relevant reference for this product please let us know.

Citations are publications that use Tocris products. Selected citations for ACEA include:

Huang et al (2016) Cannabinoid receptor subtype 2 (CB2R) agonist, GW405833 reduces agonist-induced Ca2+ oscillations in mouse pancreatic acinar cells Scientific Reports 6 29757. PMID: 27432473.

Jung et al (2016) The Orphan Nuclear Receptor ERR? Regulates Hepatic CB1 Receptor-Mediated Fibroblast Growth Factor 21 Gene Expression PLoS One 11 e0159425. PMID: 27455076.

Gianella-Borradori et al (2015) Ligand-based virtual screening identifies a family of selective cannabinoid receptor 2 agonists. Bioorg Med Chem 23 241. PMID: 25487422.

Koch et al (2015) Hypothalamic POMC neurons promote cannabinoid-induced feeding. Mol Cell Neurosci 519 45. PMID: 25707796.

Meijerink et al (2015) Inhibition of COX-2-mediated eicosanoid production plays a major role in the anti-inflammatory effects of the endocannabinoid N-docosahexaenoylethanolamine (DHEA) in macrophages. J Neuroimmune Pharmacol 172 24. PMID: 24780080.

Rivera et al (2015) Pharmacological activation of CB2 receptors counteracts the deleterious effect of ethanol on cell proliferation in the main neurogenic zones of the adult rat brain. Front Cell Neurosci 9 379. PMID: 26483633.

Zhou et al (2015) Regional effects of endocannabinoid, BDNF and FGF receptor signalling on neuroblast motility and guidance along the rostral migratory stream. Br J Pharmacol 64 32. PMID: 25481343.

Ji and Neugebauer (2014) CB1 augments mGluR5 function in medial prefrontal cortical neurons to inhibit amygdala hyperactivity in an arthritis pain model. Eur J Neurosci 39 455. PMID: 24494685.

Sánchez-Blázquez et al (2014) The calcium-sensitive σ-1 receptor prevents cannabinoids from provoking glutamate NMDA receptor hypofunction: implications in antinociception and psychotic diseases. Nature 17 1943. PMID: 24485144.

Williams et al (2014) △(9)-Tetrahydrocannabinol treatment during human monocyte differentiation reduces macrophage susceptibility to HIV-1 infection. J Neuroendocrinol 9 369. PMID: 24562630.

Benz et al (2013) Expression and functional relevance of cannabinoid receptor 1 in Hodgkin lymphoma. PLoS One 8 e81675. PMID: 24349109.

Malenczyk et al (2013) CB1 cannabinoid receptors couple to focal adhesion kinase to control insulin release. J Biol Chem 288 32685. PMID: 24089517.

Casarotto et al (2012) Opposing roles for cannabinoid receptor type-1 (CB1) and transient receptor potential vanilloid type-1 channel (TRPV1) on the modulation of panic-like responses in rats. Int J Neuropsychopharmacol 37 478. PMID: 21937980.

Gonzalez-Islas et al (2012) Tonic and transient endocannabinoid regulation of AMPAergic miniature postsynaptic currents and homeostatic plasticity in embryonic motor networks. J Cell Biol 32 13597. PMID: 23015449.

Ho et al (2012) Photoperiodic changes in endocannabinoid levels and energetic responses to altered signalling at CB1 receptors in Siberian hamsters. J Neurosci 24 1030. PMID: 22420341.

Moaddel et al (2011) Development and characterization of immobilized cannabinoid receptor (CB1/CB2) open tubular column for on-line screening. Anal Biochem 412 85. PMID: 21215722.

Ruparel et al (2011) Desensitization of transient receptor potential ankyrin 1 (TRPA1) by the TRP vanilloid 1-selective cannabinoid arachidonoyl-2 chloroethanolamine. Mol Cancer 80 117. PMID: 21441412.

Kimball et al (2010) Small intestinal cannabinoid receptor changes following a single colonic insult with oil of mustard in mice. Front Pharmacol 1 132. PMID: 21779244.

Raborn and Cabral (2010) Cannabinoid inhibition of macrophage migration to the trans-activating (Tat) protein of HIV-1 is linked to the CB(2) cannabinoid receptor. J Pharmacol Exp Ther 333 319. PMID: 20089805.

Sei et al (2010) Epistatic and functional interactions of catechol-o-methyltransferase (COMT) and AKT1 on neuregulin1-ErbB signaling in cell models. PLoS One 5 e10789. PMID: 20520724.

Fraga et al (2009) Endogenous cannabinoids induce fever through the activation of CB1 receptors. Neuropsychopharmacology 157 1494. PMID: 19681872.

Garzón et al (2009) Gz mediates the long-lasting desensitization of brain CB1 receptors and is essential for cross-tolerance with morphine. Mol Pain 5 11. PMID: 19284549.

Mendiguren and Pineda (2009) Effect of the CB(1) receptor antagonists rimonabant and AM251 on the firing rate of dorsal raphe nucleus neurons in rat brain slices. Br J Pharmacol 158 1579. PMID: 19845674.

Raborn et al (2008) The cannabinoid delta-9-tetrahydrocannabinol mediates inhibition of macrophage chemotaxis to RANTES/CCL5: linkage to the CB2 receptor. J Neuroimmune Pharmacol 3 117. PMID: 18247131.

Mathison et al (2004) Effects of cannabinoid receptor-2 activation on accelerated gastrointestinal transit in lipopolysaccharide-treated rats. Br J Pharmacol 142 1247. PMID: 15249429.

Williams et al (2003) The FGF receptor uses the endocannabinoid signaling system to couple to an axonal growth response. Mol Pharmacol 160 481. PMID: 12578907.

Do you know of a great paper that uses ACEA from Tocris? If so please let us know.show all ▼show less ▲

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