AM 630

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Cat.No. 1120 - AM 630 | C23H25IN2O3 | CAS No. 164178-33-0
Description: CB2 selective antagonist/inverse agonist
Chemical Name: 6-Iodo-2-methyl-1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl](4-methoxyphenyl)methanone
Purity: ≥98% (HPLC)
Datasheet
Citations (68)
Literature

Biological Activity

CB2 antagonist/inverse agonist (Ki = 31.2 nM) that displays 165-fold selectivity over CB1 receptors. Behaves as a weak partial/inverse agonist at CB1 receptors.

Technical Data

M. Wt 504.37
Formula C23H25IN2O3
Storage Desiccate at +4°C
Purity ≥98% (HPLC)
CAS Number 164178-33-0
PubChem ID 4302963
InChI Key JHOTYHDSLIUKCJ-UHFFFAOYSA-N
Smiles COC1=CC=C(C=C1)C(=O)C1=C(C)N(CCN2CCOCC2)C2=CC(I)=CC=C12

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.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.44 100

Preparing Stock Solutions

The following data is based on the product molecular weight 504.37. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.98 mL 9.91 mL 19.83 mL
5 mM 0.4 mL 1.98 mL 3.97 mL
10 mM 0.2 mL 0.99 mL 1.98 mL
50 mM 0.04 mL 0.2 mL 0.4 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Hosohata et al (1997) AM630 is a competitive cannabinoid receptor antagonist in the guinea pig brain. Life Sci. 61 PL115 PMID: 9284087

Hosohata et al (1997) AM630 antagonism of cannabinoid-stimulated [35S]GTPγS binding in the mouse brain. Eur.J.Pharmacol. 321 R1 PMID: 9083796

Landsman et al (1998) AM630 is an inverse agonist at the human cannabinoid CB1 receptor. Life Sci. 62 PL109 PMID: 9496703

Ross et al (1999) Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656 and AM630. Br.J.Pharmacol. 126 665 PMID: 10188977


If you know of a relevant reference for AM 630, please let us know.

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Keywords: CB2 selective antagonists inverse agonists Cannabinoids Receptors AM630 cb2r CB2 Receptors

68 Citations for AM 630

Citations are publications that use Tocris products. Selected citations for AM 630 include:

Almada (2017) The synthetic cannabinoid WIN-55,212-55,212 induced-apoptosis in cytotrophoblasts cells by a mechanism dependent on CB1 receptor. Toxicology 385 67 PMID: 28495606

Kruk-Slomka et al (2016) Correlations between the Memory-Related Behavior and the Level of Oxidative Stress Biomarkers in the Mice Brain, Provoked by an Acute Administration of CB Receptor Ligands. Neural Plast 2016 9815092 PMID: 26839719

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

Li and Kim (2016) CB2 Cannabinoid Receptor Knockout in Mice Impairs Contextual Long-Term Memory and Enhances Spatial Working Memory. Mol Pharmacol 2016 9817089 PMID: 26819779

Szczesniak et al (2016) Cannabinoid 2 receptor is a novel anti-inflammatory target in experimental proliferative vitreoretinopathy Neuropharmacology PMID: 27569993

Almada et al (2016) The endocannabinoid anandamide impairs in vitro decidualization of human cells. Reproduction 152 351 PMID: 27568210

Malek et al (2015) Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures. Neural Plast 2015 130639 PMID: 26090232

Verty et al (2015) Anti-Obesity Effect of the CB2 Receptor Agonist JWH-015 in Diet-Induced Obese Mice. PLoS One 10 e0140592 PMID: 26588700

Stanley et al (2015) Cannabidiol causes endothelium-dependent vasorelaxation of human mesenteric arteries via CB1 activation. Sleep 107 568 PMID: 26092099

Zhang et al (2015) CB2R orchestrates fibrogenesis through regulation of inflammatory response during the repair of skeletal muscle contusion. Mediators Inflamm 8 3491 PMID: 26097533

Yang et al (2015) Cannabinoid receptor CB2 is involved in tetrahydrocannabinol-induced anti-inflammation against lipopolysaccharide in MG-63 cells. PLoS One 2015 362126 PMID: 25653478

Woolcott et al (2015) High-fat diet-induced insulin resistance does not increase plasma anandamide levels or potentiate anandamide insulinotropic effect in isolated canine islets. Br J Pharmacol 10 e0123558 PMID: 25855974

Borrelli et al (2015) Palmitoylethanolamide, a naturally occurring lipid, is an orally effective intestinal anti-inflammatory agent. Sci Rep 172 142 PMID: 25205418

Savonenko et al (2015) Cannabinoid CB2 Receptors in a Mouse Model of Aβ Amyloidosis: Immunohistochemical Analysis and Suitability as a PET Biomarker of Neuroinflammation. PLoS One 10 e0129618 PMID: 26086915

Smith et al (2015) The Effects of the Endocannabinoids Anandamide and 2-Arachidonoylglycerol on Human Osteoblast Proliferation and Differentiation. Neural Plast 10 e0136546 PMID: 26414859

Krishnan and Chatterjee (2015) Differential immune mechanism to HIV-1 Tat variants and its regulation by AEA [corrected]. PLoS One 5 9887 PMID: 25943894

Sardinha et al (2014) Experimental cannabinoid 2 receptor-mediated immune modulation in sepsis. Pain 2014 978678 PMID: 24803745

Alpár et al (2014) Endocannabinoids modulate cortical development by configuring Slit2/Robo1 signalling. Pharmacol Res 5 4421 PMID: 25030704

Toguri et al (2014) Anti-inflammatory effects of cannabinoid CB(2) receptor activation in endotoxin-induced uveitis. PLoS One 171 1448 PMID: 24308861

Wang et al (2014) Treatment with a cannabinoid receptor 2 agonist decreases severity of established cystitis. Br J Pharmacol 191 1153 PMID: 24184363

Gonzalez et al (2013) Deriving dopaminergic neurons for clinical use. A practical approach. Sci Rep 3 1463 PMID: 23492920

Costola-de-Souza et al (2013) Monoacylglycerol lipase (MAGL) inhibition attenuates acute lung injury in mice. PLoS One 8 e77706 PMID: 24204926

Marini et al (2013) Characterization of cannabinoid receptor ligands in tissues natively expressing cannabinoid CB2 receptors. Br J Pharmacol 169 887 PMID: 23711022

Tchantchou and Zhang (2013) Selective inhibition of alpha/beta-hydrolase domain 6 attenuates neurodegeneration, alleviates blood brain barrier breakdown, and improves functional recovery in a mouse model of traumatic brain injury. J Neurotrauma 30 565 PMID: 23151067

Sreevalsan and Safe (2013) The cannabinoid WIN 55,212-2 decreases specificity protein transcription factors and the oncogenic cap protein eIF4E in colon cancer cells. Mol Cancer Ther 12 2483 PMID: 24030632

Wang et al (2013) Activation of cannabinoid receptor 2 inhibits experimental cystitis. Br J Pharmacol 304 R846 PMID: 23515618

Liu et al (2012) Betulinic acid targets YY1 and ErbB2 through cannabinoid receptor-dependent disruption of microRNA-27a:ZBTB10 in breast cancer. Mol Cancer Ther 11 1421 PMID: 22553354

Bolognini et al (2012) AM630 behaves as a protean ligand at the human cannabinoid CB2 receptor. Br J Pharmacol 165 2561 PMID: 21615724

García-Gutiérrez et al (2012) Chronic blockade of cannabinoid CB2 receptors induces anxiolytic-like actions associated with alterations in GABA(A) receptors. Br J Pharmacol 165 951 PMID: 21838753

Tumati et al (2012) Repeated morphine treatment-mediated hyperalgesia, allodynia and spinal glial activation are blocked by co-administration of a selective cannabinoid receptor type-2 agonist. J Neuroimmunol 244 23 PMID: 22285397

Murineddu et al (2012) Tricyclic Pyrazoles. Part 5. Novel 1,4-Dihydroindeno[1,2-c]pyrazole CB2 Ligands Using Molecular Hybridization Based on Scaffold Hopping. Open Med Chem J 6 1 PMID: 22876271

Guida et al (2012) Salvinorin A reduces mechanical allodynia and spinal neuronal hyperexcitability induced by peripheral formalin injection. Mol Pain 8 60 PMID: 22913292

Niu et al (2012) Effects of gonadal hormones on the peripheral cannabinoid receptor 1 (CB1R) system under a myositis condition in rats. Br J Pharmacol 153 2283 PMID: 22940464

Arévalo-Martín et al (2012) Early endogenous activation of CB1 and CB2 receptors after spinal cord injury is a protective response involved in spontaneous recovery. Mol Pharmacol 7 e49057 PMID: 23152849

Piro et al (2012) A dysregulated endocannabinoid-eicosanoid network supports pathogenesis in a mouse model of Alzheimer's disease. Eur J Pharmacol 1 617 PMID: 22813736

Barutta et al (2011) Protective role of cannabinoid receptor type 2 in a mouse model of diabetic nephropathy. Diabetes 60 2386 PMID: 21810593

Lombard et al (2011) Perinatal exposure to δ9-tetrahydrocannabinol triggers profound defects in T cell differentiation and function in fetal and postnatal stages of life, including decreased responsiveness to HIV antigens. J Pharmacol Exp Ther 339 607 PMID: 21831965

Bento et al (2011) β-Caryophyllene inhibits dextran sulfate sodium-induced colitis in mice through CB2 receptor activation and PPARγ pathway. Am J Pathol 178 1153 PMID: 21356367

Khasabova et al (2011) Increasing 2-arachidonoyl glycerol signaling in the periphery attenuates mechanical hyperalgesia in a model of bone cancer pain. FASEB J 64 60 PMID: 21440630

Brown et al (2010) Cannabinoid receptor-dependent and -independent anti-proliferative effects of omega-3 ethanolamides in androgen receptor-positive and -negative prostate cancer cell lines. Carcinogenesis 31 1584 PMID: 20660502

Alkaitis et al (2010) Evidence for a role of endocannabinoids, astrocytes and p38 phosphorylation in the resolution of postoperative pain. PLoS One 5 e10891 PMID: 20531936

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

Dmitrieva et al (2010) Endocannabinoid involvement in endometriosis. Pain 151 703 PMID: 20833475

Buznikov et al (2010) A putative 'pre-nervous' endocannabinoid system in early echinoderm development. Neurobiol Dis 32 43101 PMID: 19907129

Hao et al (2010) The cannabinoid WIN55,212-2 protects against oxidized LDL-induced inflammatory response in murine macrophages. J Leukoc Biol 51 2181 PMID: 20305287

Han et al (2009) CB1 and CB2 cannabinoid receptors differentially regulate the production of reactive oxygen species by macrophages. Cardiovasc Res 84 378 PMID: 19596672

Meuth et al (2009) The neuroprotective impact of the leak potassium channel TASK1 on stroke development in mice. Am J Physiol Heart Circ Physiol 33 42675 PMID: 18930826

Defer et al (2009) The cannabinoid receptor type 2 promotes cardiac myocyte and fibroblast survival and protects against ischemia/reperfusion-induced cardiomyopathy. PLoS One 23 2120 PMID: 19246487

Deveaux et al (2009) Cannabinoid CB2 receptor potentiates obesity-associated inflammation, insulin resistance and hepatic steatosis. Am J Physiol Regul Integr Comp Physiol 4 e5844 PMID: 19513120

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

Rajesh et al (2008) CB2 cannabinoid receptor agonists attenuate TNF-alpha-induced human vascular smooth muscle cell proliferation and migration. Br J Pharmacol 153 347 PMID: 17994109

Potenzieri et al (2008) The cannabinoid receptor agonist, WIN 55, 212-2, attenuates tumor-evoked hyperalgesia through peripheral mechanisms. Brain Res 1215 69 PMID: 18486111

Börner et al (2008) Analysis of promoter regions regulating basal and interleukin-4-inducible expression of the human CB1 receptor gene in T lymphocytes. Br J Pharmacol 73 1013 PMID: 18156315

Desroches et al (2008) Modulation of the anti-nociceptive effects of 2-arachidonoyl glycerol by peripherally administered FAAH and MGL inhibitors in a neuropathic pain model. J Lipid Res 155 913 PMID: 18695638

Mukhopadhyay et al (2007) Pharmacological inhibition of CB1 cannabinoid receptor protects against doxorubicin-induced cardiotoxicity. J Am Coll Cardiol 50 528 PMID: 17678736

Rajesh et al (2007) Cannabidiol attenuates high glucose-induced endothelial cell inflammatory response and barrier disruption. Am J Physiol Heart Circ Physiol 293 H610 PMID: 17384130

Rajesh et al (2007) CB2-receptor stimulation attenuates TNF-alpha-induced human endothelial cell activation, transendothelial migration of monocytes, and monocyte-endothelial adhesion. Am J Physiol Heart Circ Physiol 293 H2210 PMID: 17660390

Bátkai et al (2007) Decreased age-related cardiac dysfunction, myocardial nitrative stress, inflammatory gene expression, and apoptosis in mice lacking fatty acid amide hydrolase. Int J Clin Exp Pathol 293 H909 PMID: 17434980

Rajesh et al (2007) Cannabinoid-2 receptor agonist HU-308 protects against hepatic ischemia/reperfusion injury by attenuating oxidative stress, inflammatory response, and apoptosis. Cardiovasc Res 82 1382 PMID: 17652447

Ghasemi et al (2007) Role of the nitric oxide pathway and the endocannabinoid system in neurogenic relaxation of corpus cavernosum from biliary cirrhotic rats. Br J Pharmacol 151 591 PMID: 17486141

Saitoh et al (2007) The differential contractile responses to capsaicin and anandamide in muscle strips isolated from the rat urinary bladder. J Cell Biol 570 182 PMID: 17586490

Moezi et al (2006) Anandamide mediates hyperdynamic circulation in cirrhotic rats via CB(1) and VR(1) receptors. Dev Neurosci 149 898 PMID: 17043671

Börner et al (2006) Cannabinoid receptor type 2 agonists induce transcription of the mu-opioid receptor gene in Jurkat T cells. Cell Rep 69 1486 PMID: 16434616

Gaskari et al (2005) Role of endocannabinoids in the pathogenesis of cirrhotic cardiomyopathy in bile duct-ligated rats. Nat Commun 146 315 PMID: 16025138

Price et al (2004) Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons. Br J Pharmacol 142 257 PMID: 15155534

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. J Urol 160 481 PMID: 12578907

Jiang et al Expression and function of cannabinoid receptors CB1 and CB2 and their cognate cannabinoid ligands in murine embryonic stem cells. PLoS One 2 e641 PMID: 17653268


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