ACEA

Pricing Availability   Qty
Cat.No. 1319 - ACEA | C22H36ClNO | CAS No. 220556-69-4
Description: Potent and highly selective CB1 agonist
Alternative Names: Arachidonyl-2'-chloroethylamide
Chemical Name: N-(2-Chloroethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Purity: ≥98% (HPLC)
Datasheet
Citations (36)
Reviews
Literature

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
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 220556-69-4
PubChem ID 5311006
InChI Key SCJNCDSAIRBRIA-DOFZRALJSA-N
Smiles O=C(NCCCl)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.

Solubility Data

Solubility Soluble in ethanol (supplied pre-dissolved in anhydrous ethanol, 5mg/ml)

Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

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

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


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Keywords: ACEA, ACEA supplier, Potent, selective, CB1, agonists, Cannabinoids, Receptors, cb1r, Arachidonyl-2'-chloroethylamide, 1319, Tocris Bioscience

36 Citations for ACEA

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

Diniz et al (2019) Dual mechanism of TRKB activation by anandamide through CB1 and TRPV1 receptors. PeerJ 7 e6493 PMID: 30809460

Hohmann et al (2019) On the influence of cannabinoids on cell morphology and motility of glioblastoma cells. PLoS One 14 e0212037 PMID: 30753211

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

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

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

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

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

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

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

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

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

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

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

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

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

Li et al (2018) Adipocyte OGT governs diet-induced hyperphagia and obesity. Nat Commun 9 5103 PMID: 30504766

Balleza-Tapia et al (2018) TrpV1 receptor activation rescues neuronal function and network gamma oscillations from Aβ-induced impairment in mouse hippocampus in vitro. Elife 7 PMID: 30417826

Zhang et al (2010) Cannabinoid CB1 receptor facilitation of substance P release in the rat spinal cord, measured as neurokinin 1 receptor internalization. Eur J Neurosci 31 225 PMID: 20074214

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

Andres-Mach (2017) A long-term treatment with arachidonyl-2''chloroethylamide combined with valproate increases neurogenesis in a mouse PilC model of epilepsy. Int J Mol Sci 18 E900 PMID: 28441341

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

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

Lépicier et al (2003) Endocannabinoids protect the rat isolated heart against ischaemia. Br J Pharmacol 139 805 PMID: 12813004

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

Han (2017) Cannabinoid receptor 1 contributes to sprouted innervation in endometrial ectopic growth through mitogen-activated protein kinase activation. Brain Res 1663 132 PMID: 28322749

Bagher (2017) Bidirectional allosteric interactions between cannabinoid receptor 1 (CB1) and DAreceptor 2 long (D2L) heterotetramers. Eur J Pharmacol 813 66 PMID: 28734930

Zhang (2017) Orphan nuclear receptor ERRγ is a key regulator of human fibrinogen gene expression. PLoS One 12 e0182141 PMID: 28750085

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

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

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 Ins release. J Biol Chem 288 32685 PMID: 24089517

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

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


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