WIN 55,212-2 mesylate

Cat. No. 1038

WIN 55,212-2 mesylate C27H26N2O3.CH3SO3H [131543-23-2]

Price and Availability

For WIN 55,212-2 mesylate pricing & availability please select your country from the drop down menu:
Submit
By clicking submit you agree to accept a cookie from Tocris Bioscience. For details, please read our privacy and cookie policy.

Alternative Name: (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.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

Certificate of Analysis / Product Datasheet
Select another batch:

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.

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.

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.

If you know of a relevant reference for this product please let us know.

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

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.

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.

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.

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

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

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.

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.

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.

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.

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.

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

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

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

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.

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.

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

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.

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.

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.

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

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.

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.

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.

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.

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

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.

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.

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

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.

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

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.

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

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.

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

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.show all ▼show less ▲

View Related Products by Target

View Related Products by Product Action

Keywords: WIN 55,212-2 mesylate, supplier, potent, cannabinoid, agonists, Non-Selective, Cannabinoids, Receptors, WIN55212-2, mesylate, (R)-(+)-WIN55212, cb2r, cb1r, WIN552122, Tocris Bioscience, Non-selective Cannabinoid Agonist products

Quick Order

Find multiple products by catalog number

divider line

Pain Research Product Guide

Pain Research Product Guide

Our Pain guide highlights over 280 products for Pain research. Request copy or view PDF today.

divider line

Neurodegeneration Research Product Guide

Neurodegeneration Product Guide

Our Neurodegeneration guide highlights over 275 products for neurodegeneration research. Request copy or view PDF today.

divider line

GPCR Product Listing

GPCR Product Listing

Highlights over 450 products for GPCRs. Request copy or view PDF today.

divider line

Cannabinoid Review

Written by Roger Pertwee

Cannabinoid Receptor Ligands Scientific Review

Our Cannabinoid review gives an overview of the pharmacological ligands used to study the cannabinoid CB1 and CB2 receptors. Request copy or view PDF today.

divider line

LinkedIn Updates

Follow Tocris on LinkedIn

Follow us on LinkedIn!

Visit our LinkedIn page for the latest Tocris news, events and updates.