WIN 55,212-2 mesylate

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Cat.No. 1038 - WIN 55,212-2 mesylate | C27H26N2O3.CH3SO3H | CAS No. 131543-23-2
Description: Highly potent cannabinoid receptor agonist
Alternative Names: (R)-(+)-WIN 55212
Chemical Name: (R)-(+)-[2,3-Dihydro-5-methyl-3-(4-morpholinylmethyl)pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenylmethanone mesylate
Purity: ≥98% (HPLC)
Datasheet
Citations (61)
Literature

Biological Activity

Nanomolar affinity cannabinoid receptor agonist (Ki values are 62.3 and 3.3 nM at the human cloned CB1 and CB2 receptors respectively). S-enantiomer WIN 55,212-3 mesylate (Cat. No. 2327) also available.

Technical Data

M. Wt 522.61
Formula C27H26N2O3.CH3SO3H
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 131543-23-2
PubChem ID 6604176
InChI Key FSGCSTPOPBJYSX-VEIFNGETSA-N
Smiles CS(O)(=O)=O.CC1=C(C(=O)C2=CC=CC3=C2C=CC=C3)C2=CC=CC3=C2N1[C@H](CN1CCOCC1)CO3

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 52.26 100mM with gentle warming
ethanol 15.68 30mM with gentle warming

Preparing Stock Solutions

The following data is based on the product molecular weight 522.61. 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 1.91 mL 9.57 mL 19.13 mL
5 mM 0.38 mL 1.91 mL 3.83 mL
10 mM 0.19 mL 0.96 mL 1.91 mL
50 mM 0.04 mL 0.19 mL 0.38 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.

D'Ambra et al (1992) Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor. J.Med.Chem. 35 124 PMID: 1732519

Felder et al (1995) Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol.Pharmacol. 48 443 PMID: 7565624

Griffin et al (1998) Evaluation of cannabinoid receptor agonists and antagonists using the guanosine-5'-O-(3-[35S]thio)-triphosphate binding assay in rat cerebellar membranes. J.Pharmacol.Exp.Ther. 285 553 PMID: 9580597

Martellotta et al (1998) Self-administration of the cannabinoid receptor agonist WIN 55,212-2 in drug naive mice. Neuroscience 85 327 PMID: 9622233


If you know of a relevant reference for WIN 55,212-2 mesylate, please let us know.

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Keywords: potent cannabinoid agonists Non-Selective Cannabinoids Receptors WIN55212-2 mesylate (R)-(+)-WIN55212 cb2r cb1r WIN552122 (R)-(+)-WIN 55212 Non-selective Cannabinoids

61 Citations for WIN 55,212-2 mesylate

Citations are publications that use Tocris products. Selected citations for WIN 55,212-2 mesylate 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

Kong et al (2016) Cannabinoid WIN-55,212-2 mesylate inhibits ADAMTS-4 activity in human osteoarthritic articular chondrocytes by inhibiting expression of syndecan-1. Int J Neuropsychopharmacol 13 4569 PMID: 27082728

Szücs et al (2016) Decreased CB receptor binding and cannabinoid signaling in three brain regions of a rat model of schizophrenia Neuroscience Letters 633 87 PMID: 27639959

Zou et al (2016) Somatostatin receptor 5 is a prominent regulator of signaling pathways in cells with coexpression of Cannabinoid receptors 1 Neuroscience 340 218 PMID: 27984180

Xian et al (2016) WIN 55,212-2 inhibits the epithelial mesenchymal transition of gastric cancer cells via COX-2 signals Cell Physiology and Biochemistry 39 2149 PMID: 27802436

Mahmoud et al (2015) (4-(Bis(4-fluorophenyl)methyl)piperazin-1-yl)(cyclohexyl)methanone hydrochloride (LDK1229): a new cannabinoid CB1 receptor inverse agonist from the class of benzhydryl piperazine analogs. Mol Pharmacol 87 197 PMID: 25411367

Fanarioti et al (2015) Behavioral and neurochemical changes in mesostriatal dopaminergic regions of the rat after chronic administration of the cannabinoid receptor agonist WIN55,212-2. Int J Mol Sci 18 PMID: 25522428

Lin et al (2015) Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals. Sci Rep 16 5555 PMID: 25768340

Gentry et al (2015) TRPA1 mediates the hypothermic action of acetaminophen. Br J Pharmacol 5 12771 PMID: 26227887

Flores-Otero et al (2014) Ligand-specific endocytic dwell times control functional selectivity of the cannabinoid receptor 1. Nat Commun 5 4589 PMID: 25081814

Hruba and McMahon (2014) The cannabinoid agonist HU-210: pseudo-irreversible discriminative stimulus effects in rhesus monkeys. Neuropharmacology 727 35 PMID: 24486701

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. Mol Med Rep 17 1943 PMID: 24485144

Levin et al (2014) Effects of cannabinoid drugs on the deficit of prepulse inhibition of startle in an animal model of schizophrenia: the SHR strain. Eur J Pharmacol 5 10 PMID: 24567721

Tortoriello et al (2014) Miswiring the brain: △9-tetrahydrocannabinol disrupts cortical development by inducing an SCG10/stathmin-2 degradation pathway. Br J Pharmacol 33 668 PMID: 24469251

Caiati and Cherubini (2013) Fluoxetine impairs GABAergic signaling in hippocampal slices from neonatal rats. Front Cell Neurosci 7 63 PMID: 23641199

Marcu et al (2013) Novel insights into CB1 cannabinoid receptor signaling: a key interaction identified between the extracellular-3 loop and transmembrane helix 2. J Pharmacol Exp Ther 345 189 PMID: 23426954

Prather et al (2013) CB1 and CB2 receptors are novel molecular targets for Tamoxifen and 4OH-Tamoxifen. Biochem Biophys Res Commun 441 339 PMID: 24148245

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

Li et al (2013) Inhibition of p38/Mk2 signaling pathway improves the anti-inflammatory effect of WIN55 on mouse experimental colitis. Lab Invest 93 322 PMID: 23381627

Abush and Akirav (2013) Cannabinoids ameliorate impairments induced by chronic stress to synaptic plasticity and short-term memory. Neuropsychopharmacology 38 1521 PMID: 23426383

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

Baillie et al (2013) CB(1) receptor allosteric modulators display both agonist and signaling pathway specificity. Mol Pharmacol 83 322 PMID: 23160940

Brents et al (2012) Monohydroxylated metabolites of the K2 synthetic cannabinoid JWH-073 retain intermediate to high cannabinoid 1 receptor (CB1R) affinity and exhibit neutral antagonist to partial agonist activity. Biochem Pharmacol 83 952 PMID: 22266354

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

Laricchiuta et al (2012) CB1 receptor autoradiographic characterization of the individual differences in approach and avoidance motivation. PLoS One 7 e42111 PMID: 22848724

Caiati et al (2012) Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses. Sci Rep 2 285 PMID: 22368777

Brents et al (2011) Phase I hydroxylated metabolites of the K2 synthetic cannabinoid JWH-018 retain in vitro and in vivo cannabinoid 1 receptor affinity and activity. PLoS One 6 e21917 PMID: 21755008

Schicho et al (2011) The atypical cannabinoid O-1602 protects against experimental colitis and inhibits neutrophil recruitment. Inflamm Bowel Dis 17 1651 PMID: 21744421

Preet et al (2011) Cannabinoid receptors, CB1 and CB2, as novel targets for inhibition of non-small cell lung cancer growth and metastasis. Cancer Prev Res (Phila) 4 65 PMID: 21097714

Holderith et al (2011) Cannabinoids attenuate hippocampal γ oscillations by suppressing excitatory synaptic input onto CA3 pyramidal neurons and fast spiking basket cells. J Neurosci 589 4921 PMID: 21859823

Pan et al (2011) Alterations of endocannabinoid signaling, synaptic plasticity, learning, and memory in monoacylglycerol lipase knock-out mice. J Cell Biol 31 13420 PMID: 21940435

Kim and Alger (2010) Reduction in endocannabinoid tone is a homeostatic mechanism for specific inhibitory synapses. Nat Neurosci 13 592 PMID: 20348918

Wyeth et al (2010) Selective reduction of cholecystokinin-positive basket cell innervation in a model of temporal lobe epilepsy. J Neurosci 30 8993 PMID: 20592220

Acuna-Goycolea et al (2010) Cannabinoids excite circadian clock neurons. PLoS One 30 10061 PMID: 20668190

Farkas et al (2010) Retrograde endocannabinoid signaling reduces GABAergic synaptic transmission to gonadotropin-releasing hormone neurons. J Biomol Screen 151 5818 PMID: 20926585

Jones et al (2010) Cannabidiol displays antiepileptiform and antiseizure properties in vitro and in vivo. Br J Pharmacol 332 569 PMID: 19906779

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

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

Carney et al (2009) Cannabinoid regulation of nitric oxide synthase I (nNOS) in neuronal cells. J Neuroimmune Pharmacol 4 338 PMID: 19365734

Huerta et al (2009) Effects of cannabinoids on caffeine contractures in slow and fast skeletal muscle fibers of the frog. J Membr Biol 229 91 PMID: 19506935

McGuinness et al (2009) Characterizing cannabinoid CB2 receptor ligands using DiscoveRx PathHunter β-arrestin assay. Int J Neuropsychopharmacol 14 49 PMID: 19171920

Ho and Gardiner (2009) Acute hypertension reveals depressor and vasodilator effects of cannabinoids in conscious rats. Front Pharmacol 156 94 PMID: 19133994

Gibson et al (2008) TRPV1 channels mediate long-term depression at synapses on hippocampal interneurons. Neuron 57 746 PMID: 18341994

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

Kapur et al (2008) Mapping the structural requirements in the CB1 cannabinoid receptor transmembrane helix II for signal transduction. J Pharmacol Exp Ther 325 341 PMID: 18174385

Karson et al (2008) Cholecystokinin inhibits endocannabinoid-sensitive hippocampal IPSPs and stimulates others. J Physiol 54 117 PMID: 17689570

Marinelli et al (2007) N-arachidonoyl-dopamine tunes synaptic transmission onto dopaminergic neurons by activating both cannabinoid and vanilloid receptors. Neuropsychopharmacology 32 298 PMID: 16760924

Huang et al (2007) Cannabinoids excite hypothalamic melanin-concentrating hormone but inhibit hypocretin/orexin neurons: implications for cannabinoid actions on food intake and cognitive arousal. J Neurosci 27 4870 PMID: 17475795

Pertwee et al (2007) The psychoactive plant cannabinoid, Delta9-tetrahydrocannabinol, is antagonized by Delta8- and Delta9-tetrahydrocannabivarin in mice in vivo. Br J Pharmacol 150 586 PMID: 17245367

Narushima et al (2007) Tonic enhancement of endocannabinoid-mediated retrograde suppression of inhibition by cholinergic interneuron activity in the striatum. J Neurosci 27 496 PMID: 17234582

Kelm et al (2007) Calcium release from presynaptic internal stores is required for ethanol to increase spontaneous γ-aminobutyric acid release onto cerebellum Purkinje neurons. J Neurosci 323 356 PMID: 17652632

Thomas et al (2005) Evidence that the plant cannabinoid Delta9-tetrahydrocannabivarin is a cannabinoid CB1 and CB2 receptor antagonist. Br J Pharmacol 146 917 PMID: 16205722

Hoffman et al (2005) Species and strain differences in the expression of a novel glutamate-modulating cannabinoid receptor in the rodent hippocampus. J Lipid Res 22 2387 PMID: 16262678

MacNaughton et al (2004) Distribution and function of the cannabinoid-1 receptor in the modulation of ion transport in the guinea pig ileum: relationship to capsaicin-sensitive nerves. Eur J Neurosci 286 G863 PMID: 14701723

Costa et al (2004) Repeated treatment with the synthetic cannabinoid WIN 55,212-2 reduces both hyperalgesia and production of pronociceptive mediators in a rat model of neuropathic pain. J Neurosci 141 42586 PMID: 14662732

Galarreta et al (2004) Electrical coupling among irregular-spiking GABAergic interneurons expressing cannabinoid receptors. J Pharmacol Exp Ther 24 9770 PMID: 15525762

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

Craib et al (2001) A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus. PLoS One 134 42581 PMID: 11522594

Michalski et al Cannabinoids reduce markers of inflammation and fibrosis in pancreatic stellate cells. Am J Physiol Gastrointest Liver Physiol 3 e1701 PMID: 18301776

Sinnayah et al Feeding induced by cannabinoids is mediated independently of the melanocortin system. Endocrinology 3 e2202 PMID: 18493584


Do you know of a great paper that uses WIN 55,212-2 mesylate from Tocris? If so please let us know.

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