WIN 55,212-2 mesylate

Cat. No. 1038

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

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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 / Safety Data Sheet

Certificate of Analysis: View current batch
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Safety Data Sheet: View Safety Data Sheet

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:

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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