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 and non-selective CB 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 (101)
Reviews
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 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.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
ethanol 15.68 30 with gentle warming
DMSO 52.26 100 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.

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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References

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

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


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101 Citations for WIN 55,212-2 mesylate

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

Baker et al (2017) Big conductance calcium-activated potassium channel openers control spasticity without sedation. Br J Pharmacol 174 2662 PMID: 28677901

Abush and Akirav (2012) Short- and long-term cognitive effects of chronic cannabinoids administration in late-adolescence rats. PLoS One 7 e31731 PMID: 22348124

Segev et al (2012) Stress hormones receptors in the amygdala mediate the effects of stress on the consolidation, but not the retrieval, of a non aversive spatial task. PLoS One 7 e29988 PMID: 22253850

Giordano et al (2012) TRPV1-dependent and -independent alterations in the limbic cortex of neuropathic mice: impact on glial caspases and pain perception. Cereb Cortex 22 2495 PMID: 22139792

Zhong et al (2012) Phosphodiesterase 4 inhibition impairs cocaine-induced inhibitory synaptic plasticity and conditioned place preference. Neuropsychopharmacology 37 2377 PMID: 22713909

Kargl et al (2012) The cannabinoid receptor CB1 modulates the signaling properties of the lysophosphatidylinositol receptor GPR55. J Biol Chem 287 44234 PMID: 23161546

Kazemi et al (2012) Effect of cannabinoid receptor activation on spreading depression. Iran J Basic Med Sci 15 926 PMID: 23493641

Sideris et al (2012) A Role for the Cannabinoid 1 Receptor in Neuronal Differentiation of Adult Spinal Cord Progenitors in vitro is Revealed through Pharmacological Inhibition and Genetic Deletion. Front Neurosci 6 4 PMID: 22291615

Izzo et al (2012) Inhibitory effect of cannabichromene, a major non-psychotropic cannabinoid extracted from Cannabis sativa, on inflammation-induced hypermotility in mice. Br J Pharmacol 166 1444 PMID: 22300105

Price et al (2009) WIN55,212-2, a cannabinoid receptor agonist, protects against nigrostriatal cell loss in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine mouse model of Parkinson's disease. Eur J Neurosci 29 2177 PMID: 19490092

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

Melis et al (2004) Prefrontal cortex stimulation induces 2-arachidonoyl-glycerol-mediated suppression of excitation in dopamine neurons. J Neurosci 24 10707 PMID: 15564588

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

Barann et al (2002) Direct inhibition by cannabinoids of human 5-HT3A receptors: probable involvement of an allosteric modulatory site. Br J Pharmacol 137 589 PMID: 12381672

McKallip et al (2002) Targeting CB2 cannabinoid receptors as a novel therapy to treat malignant lymphoblastic disease. Blood 100 627 PMID: 12091357

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

Okada et al (2011) High extracellular Ca2+ stimulates Ca2+-activated Cl- currents in frog parathyroid cells through the mediation of arachidonic acid cascade. PLoS One 6 e19158 PMID: 21559478

Thompson and Perkel (2011) Endocannabinoids mediate synaptic plasticity at glutamatergic synapses on spiny neurons within a basal ganglia nucleus necessary for song learning. J Neurophysiol 105 1159 PMID: 21177997

Sousa et al (2011) Regulation of hippocampal cannabinoid CB1 receptor actions by adenosine A1 receptors and chronic caffeine administration: implications for the effects of δ9-tetrahydrocannabinol on spatial memory. Neuropsychopharmacology 36 472 PMID: 20927050

Tan et al (2011) Cannabinoid transmission in the basolateral amygdala modulates fear memory formation via functional inputs to the prelimbic cortex. J Neurosci 31 5300 PMID: 21471365

Tozzi et al (2011) The distinct role of medium spiny neurons and cholinergic interneurons in the D2/A2A receptor interaction in the striatum: implications for Parkinson's disease. J Neurosci 31 1850 PMID: 21289195

Lecca et al (2011) Effects of drugs of abuse on putative rostromedial tegmental neurons, inhibitory afferents to midbrain dopamine cells. Neuropsychopharmacology 36 589 PMID: 21048703

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

Bridges et al (2001) The synthetic cannabinoid WIN55,212-2 attenuates hyperalgesia and allodynia in a rat model of neuropathic pain. Br J Pharmacol 133 586 PMID: 11399676

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

Izzo et al (2000) Central and peripheral cannabinoid modulation of gastrointestinal transit in physiological states or during the diarrhoea induced by croton oil. Br J Pharmacol 129 1627 PMID: 10780967

Izzo et al (2000) Modulation of peristalsis by cannabinoid CB(1) ligands in the isolated guinea-pig ileum. Br J Pharmacol 129 984 PMID: 10696099

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

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

Ford (2017) Characterization of structurally novel G protein biased CB1 agonists: implications for drug development. Pharmacol Res 125 161 PMID: 28838808

Fatahi (2017) Involvement of cannabinoid system in the nucleus accumbens on delay-based decision making in the rat. Behav Brain Res. 337 107 PMID: 28987618

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

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

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

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

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

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 et al (2008) Interactions between CB(1) receptors and TRPV1 channels mediated by 12-HPETE are cytotoxic to mesencephalic dopaminergic neurons. Br J Pharmacol 155 253 PMID: 18552868

Akerman et al (2007) Cannabinoid (CB1) receptor activation inhibits trigeminovascular neurons. J Pharmacol Exp Ther 320 64 PMID: 17018694

Hoffman et al (2007) Opposing actions of chronic Delta9-tetrahydrocannabinol and cannabinoid antagonists on hippocampal long-term potentiation. Learn Mem 14 63 PMID: 17202425

Cachope et al (2007) Potentiation of electrical and chemical synaptic transmission mediated by endocannabinoids. Neuron 56 1034 PMID: 18093525

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

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

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

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

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

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

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

Kargl et al (2013) A selective antagonist reveals a potential role of G protein-coupled receptor 55 in platelet and endothelial cell function. J Pharmacol Exp Ther 346 54 PMID: 23639801

Akerman et al (2013) Endocannabinoids in the brainstem modulate dural trigeminovascular nociceptive traffic via CB1 and "triptan" receptors: implications in migraine. J Neurosci 33 14869 PMID: 24027286

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

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

Monory et al (2006) The endocannabinoid system controls key epileptogenic circuits in the hippocampus. Neuron 51 455 PMID: 16908411

Haj-Dahmane (2005) The wake-promoting peptide orexin-B inhibits glutamatergic transmission to dorsal raphe nucleus serotonin neurons through retrograde endocannabinoid signaling. J Neurosci 25 896 PMID: 15673670

Kettunen et al (2005) Neuromodulation via conditional release of endocannabinoids in the spinal locomotor network. Neuron 45 95 PMID: 15629705

Okada et al (2005) Biophysical properties of voltage-gated Na+ channels in frog parathyroid cells and their modulation by cannabinoids. J Exp Biol 208 4747 PMID: 16326956

Cawston et al (2013) Real-time characterization of cannabinoid receptor 1 (CB1 ) allosteric modulators reveals novel mechanism of action. Br J Pharmacol 170 893 PMID: 23937487

Uhelski et al (2013) The non-selective cannabinoid receptor agonist WIN 55,212-2 attenuates responses of C-fiber nociceptors in a murine model of cancer pain. Neuroscience 247 84 PMID: 23673278

Hoffman et al (2010) Control of cannabinoid CB1 receptor function on glutamate axon terminals by endogenous adenosine acting at A1 receptors. J Neurosci 30 545 PMID: 20071517

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

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

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

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

Chiu and Castillo (2008) Input-specific plasticity at excitatory synapses mediated by endocannabinoids in the dentate gyrus. Neuropharmacology 54 68 PMID: 17706254

Huang et al (2008) Roles of endocannabinoids in heterosynaptic long-term depression of excitatory synaptic transmission in visual cortex of young mice. J Neurosci 28 7074 PMID: 18614676

Kelm et al (2008) The role of protein kinase A in the ethanol-induced increase in spontaneous GABA release onto cerebellar Purkinje neurons. J Neurophysiol 100 3417 PMID: 18945815


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