WIN 55,212-2 mesylate

  ( 88 citations )    
Product Datasheet
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
Product Details
Citations (88)
Supplemental Products
Reviews
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
  • 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
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Citations:

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

88 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. Involvement of cannabinoid system in the nucleus accumbens on delay-based decision making in the rat.
    Authors: Fatahi
    Behav Brain Res.  2017;337:107
  5. Characterization of structurally novel G protein biased CB1 agonists: implications for drug development.
    Authors: Ford
    Pharmacol Res  2017;125:161
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. (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
  12. TRPA1 mediates the hypothermic action of acetaminophen.
    Authors: Gentry Et al.
    Br J Pharmacol  2015;5:12771
  13. 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
  14. Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals.
    Authors: Lin Et al.
    Sci Rep  2015;16:5555
  15. The cannabinoid agonist HU-210: pseudo-irreversible discriminative stimulus effects in rhesus monkeys.
    Authors: Hruba and McMahon
    Neuropharmacology  2014;727:35
  16. Ligand-specific endocytic dwell times control functional selectivity of the cannabinoid receptor 1.
    Authors: Flores-Otero Et al.
    Nat Commun  2014;5:4589
  17. 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
  18. 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
  19. 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
  20. 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
  21. CB(1) receptor allosteric modulators display both agonist and signaling pathway specificity.
    Authors: Baillie Et al.
    Mol Pharmacol  2013;83:322
  22. Fluoxetine impairs GABAergic signaling in hippocampal slices from neonatal rats.
    Authors: Caiati and Cherubini
    Front Cell Neurosci  2013;7:63
  23. CB1 and CB2 receptors are novel molecular targets for Tamoxifen and 4OH-Tamoxifen.
    Authors: Prather Et al.
    Biochem Biophys Res Commun  2013;441:339
  24. Cannabinoids ameliorate impairments induced by chronic stress to synaptic plasticity and short-term memory.
    Authors: Abush and Akirav
    Neuropsychopharmacology  2013;38:1521
  25. 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
  26. The non-selective cannabinoid receptor agonist WIN 55,212-2 attenuates responses of C-fiber nociceptors in a murine model of cancer pain.
    Authors: Uhelski Et al.
    Neuroscience  2013;247:84
  27. Real-time characterization of cannabinoid receptor 1 (CB1 ) allosteric modulators reveals novel mechanism of action.
    Authors: Cawston Et al.
    Br J Pharmacol  2013;170:893
  28. Characterization of cannabinoid receptor ligands in tissues natively expressing cannabinoid CB2 receptors.
    Authors: Marini Et al.
    Br J Pharmacol  2013;169:887
  29. 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
  30. 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
  31. CB1 receptor autoradiographic characterization of the individual differences in approach and avoidance motivation.
    Authors: Laricchiuta Et al.
    PLoS One  2012;7:e42111
  32. Short- and long-term cognitive effects of chronic cannabinoids administration in late-adolescence rats.
    Authors: Abush and Akirav
    PLoS One  2012;7:e31731
  33. Stress hormones receptors in the amygdala mediate the effects of stress on the consolidation, but not the retrieval, of a non aversive spatial task.
    Authors: Segev Et al.
    PLoS One  2012;7:e29988
  34. 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.
    Authors: Sideris Et al.
    Front Neurosci  2012;6:4
  35. Phosphodiesterase 4 inhibition impairs cocaine-induced inhibitory synaptic plasticity and conditioned place preference.
    Authors: Zhong Et al.
    Neuropsychopharmacology  2012;37:2377
  36. Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses.
    Authors: Caiati Et al.
    Sci Rep  2012;2:285
  37. The cannabinoid receptor CB1 modulates the signaling properties of the lysophosphatidylinositol receptor GPR55.
    Authors: Kargl Et al.
    J Biol Chem  2012;287:44234
  38. TRPV1-dependent and -independent alterations in the limbic cortex of neuropathic mice: impact on glial caspases and pain perception.
    Authors: Giordano Et al.
    Cereb Cortex  2012;22:2495
  39. Effect of cannabinoid receptor activation on spreading depression.
    Authors: Kazemi Et al.
    Iran J Basic Med Sci  2012;15:926
  40. 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
  41. 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
  42. High extracellular Ca2+ stimulates Ca2+-activated Cl- currents in frog parathyroid cells through the mediation of arachidonic acid cascade.
    Authors: Okada Et al.
    PLoS One  2011;6:e19158
  43. 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
  44. 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
  45. Effects of drugs of abuse on putative rostromedial tegmental neurons, inhibitory afferents to midbrain dopamine cells.
    Authors: Lecca Et al.
    Neuropsychopharmacology  2011;36:589
  46. 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.
    Authors: Sousa Et al.
    Neuropsychopharmacology  2011;36:472
  47. Cannabinoid transmission in the basolateral amygdala modulates fear memory formation via functional inputs to the prelimbic cortex.
    Authors: Tan Et al.
    J Neurosci  2011;31:5300
  48. The distinct role of medium spiny neurons and cholinergic interneurons in the D2/A2A receptor interaction in the striatum: implications for Parkinson's disease.
    Authors: Tozzi Et al.
    J Neurosci  2011;31:1850
  49. 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
  50. The atypical cannabinoid O-1602 protects against experimental colitis and inhibits neutrophil recruitment.
    Authors: Schicho Et al.
    Inflamm Bowel Dis  2011;17:1651
  51. Endocannabinoids mediate synaptic plasticity at glutamatergic synapses on spiny neurons within a basal ganglia nucleus necessary for song learning.
    Authors: Thompson and Perkel
    J Neurophysiol  2011;105:1159
  52. The cannabinoid WIN55,212-2 protects against oxidized LDL-induced inflammatory response in murine macrophages.
    Authors: Hao Et al.
    J Neurosci  2010;51:2181
  53. Cannabidiol displays antiepileptiform and antiseizure properties in vitro and in vivo.
    Authors: Jones Et al.
    Br J Pharmacol  2010;332:569
  54. Selective reduction of cholecystokinin-positive basket cell innervation in a model of temporal lobe epilepsy.
    Authors: Wyeth Et al.
    J Neurosci  2010;30:8993
  55. Cannabinoids excite circadian clock neurons.
    Authors: Acuna-Goycolea Et al.
    PLoS One  2010;30:10061
  56. Retrograde endocannabinoid signaling reduces GABAergic synaptic transmission to gonadotropin-releasing hormone neurons.
    Authors: Farkas Et al.
    J Biomol Screen  2010;151:5818
  57. Reduction in endocannabinoid tone is a homeostatic mechanism for specific inhibitory synapses.
    Authors: Kim and Alger
    Nat Neurosci  2010;13:592
  58. 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
  59. Cannabinoid regulation of nitric oxide synthase I (nNOS) in neuronal cells.
    Authors: Carney Et al.
    J Neuroimmune Pharmacol  2009;4:338
  60. 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.
    Authors: Price Et al.
    Eur J Neurosci  2009;29:2177
  61. 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
  62. Acute hypertension reveals depressor and vasodilator effects of cannabinoids in conscious rats.
    Authors: Ho and Gardiner
    Front Pharmacol  2009;156:94
  63. Characterizing cannabinoid CB2 receptor ligands using DiscoveRx PathHunter β-arrestin assay.
    Authors: McGuinness Et al.
    Int J Neuropsychopharmacol  2009;14:49
  64. TRPV1 channels mediate long-term depression at synapses on hippocampal interneurons.
    Authors: Gibson Et al.
    Neuron  2008;57:746
  65. Input-specific plasticity at excitatory synapses mediated by endocannabinoids in the dentate gyrus.
    Authors: Chiu and Castillo
    Neuropharmacology  2008;54:68
  66. Cholecystokinin inhibits endocannabinoid-sensitive hippocampal IPSPs and stimulates others.
    Authors: Karson Et al.
    J Physiol  2008;54:117
  67. 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
  68. The cannabinoid receptor agonist, WIN 55, 212-2, attenuates tumor-evoked hyperalgesia through peripheral mechanisms.
    Authors: Potenzieri Et al.
    Brain Res  2008;1215:69
  69. Potentiation of electrical and chemical synaptic transmission mediated by endocannabinoids.
    Authors: Cachope Et al.
    Neuron  2007;56:1034
  70. N-arachidonoyl-dopamine tunes synaptic transmission onto dopaminergic neurons by activating both cannabinoid and vanilloid receptors.
    Authors: Marinelli Et al.
    Neuropsychopharmacology  2007;32:298
  71. 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
  72. 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
  73. 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
  74. 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
  75. Opposing actions of chronic Delta9-tetrahydrocannabinol and cannabinoid antagonists on hippocampal long-term potentiation.
    Authors: Hoffman Et al.
    Learn Mem  2007;14:63
  76. 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
  77. 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
  78. 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
  79. Electrical coupling among irregular-spiking GABAergic interneurons expressing cannabinoid receptors.
    Authors: Galarreta Et al.
    J Pharmacol Exp Ther  2004;24:9770
  80. Prefrontal cortex stimulation induces 2-arachidonoyl-glycerol-mediated suppression of excitation in dopamine neurons.
    Authors: Melis Et al.
    J Neurosci  2004;24:10707
  81. 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
  82. The FGF receptor uses the endocannabinoid signaling system to couple to an axonal growth response.
    Authors: Williams Et al.
    EMBO J  2003;160:481
  83. Direct inhibition by cannabinoids of human 5-HT3A receptors: probable involvement of an allosteric modulatory site.
    Authors: Barann Et al.
    Br J Pharmacol  2002;137:589
  84. Targeting CB2 cannabinoid receptors as a novel therapy to treat malignant lymphoblastic disease.
    Authors: McKallip Et al.
    Blood  2002;100:627
  85. 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
  86. The synthetic cannabinoid WIN55,212-2 attenuates hyperalgesia and allodynia in a rat model of neuropathic pain.
    Authors: Bridges Et al.
    Br J Pharmacol  2001;133:586
  87. Modulation of peristalsis by cannabinoid CB(1) ligands in the isolated guinea-pig ileum.
    Authors: Izzo Et al.
    Br J Pharmacol  2000;129:984
  88. Central and peripheral cannabinoid modulation of gastrointestinal transit in physiological states or during the diarrhoea induced by croton oil.
    Authors: Izzo Et al.
    Br J Pharmacol  2000;129:1627
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