Catalog Number: 1038
Alternate 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
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
  • Solubility:
    Soluble to 30 mM in ethanol with gentle warming and to 100 mM in DMSO with gentle warming
  • Purity:
    >98%
  • Storage:
    Store at +4°C
  • CAS No:
    131543-23-2
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.
Additional Information
Other Product-Specific Information:
Citations:

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

62 Citations: Showing 1 - 10
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  1. Feeding induced by cannabinoids is mediated independently of the melanocortin system.
    Authors: Sinnayah Et al.
    Endocrinology ;3:e2202
  2. Cannabinoids reduce markers of inflammation and fibrosis in pancreatic stellate cells.
    Authors: Michalski Et al.
    Am J Physiol Gastrointest Liver Physiol ;3:e1701
  3. The synthetic cannabinoid WIN-55,212-55,212 induced-apoptosis in cytotrophoblasts cells by a mechanism dependent on CB1 receptor.
    Authors: Almada
    Toxicology 2017;385:67
  4. Characterization of structurally novel G protein biased CB1 agonists: implications for drug development.
    Authors: Ford
    Pharmacol Res 2017;125:161
  5. Decreased CB receptor binding and cannabinoid signaling in three brain regions of a rat model of schizophrenia
    Authors: Szücs Et al.
    Neuroscience Letters 2016;633:87
  6. WIN 55,212-2 inhibits the epithelial mesenchymal transition of gastric cancer cells via COX-2 signals
    Authors: Xian Et al.
    Cell Physiology and Biochemistry 2016;39:2149
  7. Somatostatin receptor 5 is a prominent regulator of signaling pathways in cells with coexpression of Cannabinoid receptors 1
    Authors: Zou Et al.
    Neuroscience 2016;340:218
  8. 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.
    Authors: Kruk-Slomka Et al.
    Neural Plast 2016;2016:9815092
  9. Cannabinoid WIN-55,212-2 mesylate inhibits ADAMTS-4 activity in human osteoarthritic articular chondrocytes by inhibiting expression of syndecan-1.
    Authors: Kong Et al.
    Int J Neuropsychopharmacol 2016;13:4569
  10. (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.
    Authors: Mahmoud Et al.
    Mol Pharmacol 2015;87:197
  11. TRPA1 mediates the hypothermic action of acetaminophen.
    Authors: Gentry Et al.
    Br J Pharmacol 2015;5:12771
  12. Behavioral and neurochemical changes in mesostriatal dopaminergic regions of the rat after chronic administration of the cannabinoid receptor agonist WIN55,212-2.
    Authors: Fanarioti Et al.
    Int J Mol Sci 2015;18
  13. Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals.
    Authors: Lin Et al.
    Sci Rep 2015;16:5555
  14. The cannabinoid agonist HU-210: pseudo-irreversible discriminative stimulus effects in rhesus monkeys.
    Authors: Hruba and McMahon
    Neuropharmacology 2014;727:35
  15. Ligand-specific endocytic dwell times control functional selectivity of the cannabinoid receptor 1.
    Authors: Flores-Otero Et al.
    Nat Commun 2014;5:4589
  16. Effects of cannabinoid drugs on the deficit of prepulse inhibition of startle in an animal model of schizophrenia: the SHR strain.
    Authors: Levin Et al.
    Eur J Pharmacol 2014;5:10
  17. Miswiring the brain: △9-tetrahydrocannabinol disrupts cortical development by inducing an SCG10/stathmin-2 degradation pathway.
    Authors: Tortoriello Et al.
    Br J Pharmacol 2014;33:668
  18. The calcium-sensitive σ-1 receptor prevents cannabinoids from provoking glutamate NMDA receptor hypofunction: implications in antinociception and psychotic diseases.
    Authors: Sánchez-Blázquez Et al.
    Mol Med Rep 2014;17:1943
  19. Inhibition of p38/Mk2 signaling pathway improves the anti-inflammatory effect of WIN55 on mouse experimental colitis.
    Authors: Li Et al.
    Lab Invest 2013;93:322
  20. CB(1) receptor allosteric modulators display both agonist and signaling pathway specificity.
    Authors: Baillie Et al.
    Mol Pharmacol 2013;83:322
  21. Fluoxetine impairs GABAergic signaling in hippocampal slices from neonatal rats.
    Authors: Caiati and Cherubini
    Front Cell Neurosci 2013;7:63
  22. CB1 and CB2 receptors are novel molecular targets for Tamoxifen and 4OH-Tamoxifen.
    Authors: Prather Et al.
    Biochem Biophys Res Commun 2013;441:339
  23. Cannabinoids ameliorate impairments induced by chronic stress to synaptic plasticity and short-term memory.
    Authors: Abush and Akirav
    Neuropsychopharmacology 2013;38:1521
  24. Novel insights into CB1 cannabinoid receptor signaling: a key interaction identified between the extracellular-3 loop and transmembrane helix 2.
    Authors: Marcu Et al.
    J Pharmacol Exp Ther 2013;345:189
  25. Characterization of cannabinoid receptor ligands in tissues natively expressing cannabinoid CB2 receptors.
    Authors: Marini Et al.
    Br J Pharmacol 2013;169:887
  26. The cannabinoid WIN 55,212-2 decreases specificity protein transcription factors and the oncogenic cap protein eIF4E in colon cancer cells.
    Authors: Sreevalsan and Safe
    Mol Cancer Ther 2013;12:2483
  27. 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.
    Authors: Brents Et al.
    Biochem Pharmacol 2012;83:952
  28. CB1 receptor autoradiographic characterization of the individual differences in approach and avoidance motivation.
    Authors: Laricchiuta Et al.
    PLoS One 2012;7:e42111
  29. Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses.
    Authors: Caiati Et al.
    Sci Rep 2012;2:285
  30. Betulinic acid targets YY1 and ErbB2 through cannabinoid receptor-dependent disruption of microRNA-27a:ZBTB10 in breast cancer.
    Authors: Liu Et al.
    Mol Cancer Ther 2012;11:1421
  31. Phase I hydroxylated metabolites of the K2 synthetic cannabinoid JWH-018 retain in vitro and in vivo cannabinoid 1 receptor affinity and activity.
    Authors: Brents Et al.
    PLoS One 2011;6:e21917
  32. Cannabinoids attenuate hippocampal γ oscillations by suppressing excitatory synaptic input onto CA3 pyramidal neurons and fast spiking basket cells.
    Authors: Holderith Et al.
    J Neurosci 2011;589:4921
  33. Cannabinoid receptors, CB1 and CB2, as novel targets for inhibition of non-small cell lung cancer growth and metastasis.
    Authors: Preet Et al.
    Cancer Prev Res (Phila) 2011;4:65
  34. Alterations of endocannabinoid signaling, synaptic plasticity, learning, and memory in monoacylglycerol lipase knock-out mice.
    Authors: Pan Et al.
    J Cell Biol 2011;31:13420
  35. The atypical cannabinoid O-1602 protects against experimental colitis and inhibits neutrophil recruitment.
    Authors: Schicho Et al.
    Inflamm Bowel Dis 2011;17:1651
  36. The cannabinoid WIN55,212-2 protects against oxidized LDL-induced inflammatory response in murine macrophages.
    Authors: Hao Et al.
    J Neurosci 2010;51:2181
  37. Cannabidiol displays antiepileptiform and antiseizure properties in vitro and in vivo.
    Authors: Jones Et al.
    Br J Pharmacol 2010;332:569
  38. Selective reduction of cholecystokinin-positive basket cell innervation in a model of temporal lobe epilepsy.
    Authors: Wyeth Et al.
    J Neurosci 2010;30:8993
  39. Cannabinoids excite circadian clock neurons.
    Authors: Acuna-Goycolea Et al.
    PLoS One 2010;30:10061
  40. Retrograde endocannabinoid signaling reduces GABAergic synaptic transmission to gonadotropin-releasing hormone neurons.
    Authors: Farkas Et al.
    J Biomol Screen 2010;151:5818
  41. Reduction in endocannabinoid tone is a homeostatic mechanism for specific inhibitory synapses.
    Authors: Kim and Alger
    Nat Neurosci 2010;13:592
  42. Gz mediates the long-lasting desensitization of brain CB1 receptors and is essential for cross-tolerance with morphine.
    Authors: Garzón Et al.
    Mol Pain 2009;5:11
  43. Cannabinoid regulation of nitric oxide synthase I (nNOS) in neuronal cells.
    Authors: Carney Et al.
    J Neuroimmune Pharmacol 2009;4:338
  44. Effects of cannabinoids on caffeine contractures in slow and fast skeletal muscle fibers of the frog.
    Authors: Huerta Et al.
    J Membr Biol 2009;229:91
  45. Acute hypertension reveals depressor and vasodilator effects of cannabinoids in conscious rats.
    Authors: Ho and Gardiner
    Front Pharmacol 2009;156:94
  46. Characterizing cannabinoid CB2 receptor ligands using DiscoveRx PathHunter β-arrestin assay.
    Authors: McGuinness Et al.
    Int J Neuropsychopharmacol 2009;14:49
  47. TRPV1 channels mediate long-term depression at synapses on hippocampal interneurons.
    Authors: Gibson Et al.
    Neuron 2008;57:746
  48. Cholecystokinin inhibits endocannabinoid-sensitive hippocampal IPSPs and stimulates others.
    Authors: Karson Et al.
    J Physiol 2008;54:117
  49. Mapping the structural requirements in the CB1 cannabinoid receptor transmembrane helix II for signal transduction.
    Authors: Kapur Et al.
    J Pharmacol Exp Ther 2008;325:341
  50. The cannabinoid receptor agonist, WIN 55, 212-2, attenuates tumor-evoked hyperalgesia through peripheral mechanisms.
    Authors: Potenzieri Et al.
    Brain Res 2008;1215:69
  51. N-arachidonoyl-dopamine tunes synaptic transmission onto dopaminergic neurons by activating both cannabinoid and vanilloid receptors.
    Authors: Marinelli Et al.
    Neuropsychopharmacology 2007;32:298
  52. Calcium release from presynaptic internal stores is required for ethanol to increase spontaneous γ-aminobutyric acid release onto cerebellum Purkinje neurons.
    Authors: Kelm Et al.
    J Neurosci 2007;323:356
  53. Tonic enhancement of endocannabinoid-mediated retrograde suppression of inhibition by cholinergic interneuron activity in the striatum.
    Authors: Narushima Et al.
    J Neurosci 2007;27:496
  54. Cannabinoids excite hypothalamic melanin-concentrating hormone but inhibit hypocretin/orexin neurons: implications for cannabinoid actions on food intake and cognitive arousal.
    Authors: Huang Et al.
    J Neurosci 2007;27:4870
  55. The psychoactive plant cannabinoid, Delta9-tetrahydrocannabinol, is antagonized by Delta8- and Delta9-tetrahydrocannabivarin in mice in vivo.
    Authors: Pertwee Et al.
    Br J Pharmacol 2007;150:586
  56. Species and strain differences in the expression of a novel glutamate-modulating cannabinoid receptor in the rodent hippocampus.
    Authors: Hoffman Et al.
    J Lipid Res 2005;22:2387
  57. Evidence that the plant cannabinoid Delta9-tetrahydrocannabivarin is a cannabinoid CB1 and CB2 receptor antagonist.
    Authors: Thomas Et al.
    Br J Pharmacol 2005;146:917
  58. Distribution and function of the cannabinoid-1 receptor in the modulation of ion transport in the guinea pig ileum: relationship to capsaicin-sensitive nerves.
    Authors: MacNaughton Et al.
    Eur J Neurosci 2004;286:G863
  59. Electrical coupling among irregular-spiking GABAergic interneurons expressing cannabinoid receptors.
    Authors: Galarreta Et al.
    J Pharmacol Exp Ther 2004;24:9770
  60. 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.
    Authors: Costa Et al.
    J Neurosci 2004;141:42586
  61. The FGF receptor uses the endocannabinoid signaling system to couple to an axonal growth response.
    Authors: Williams Et al.
    EMBO J 2003;160:481
  62. A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus.
    Authors: Craib Et al.
    PLoS One 2001;134:42581
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