WIN 55,212-3 mesylate

Discontinued Product

WIN 55,212-3 mesylate (Cat. No. 2327) has been withdrawn from sale for commercial reasons.
Description: CB2 antagonist/CB1 partial inverse agonist; enantiomer of WIN 55,212-2 (Cat. No. 1038)
Alternative Names: (S)-(-)-WIN 55,212
Chemical Name: [(3S)-2,3-Dihydro-5-methyl-3-(4-morpholinylmethyl)pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenyl-methanone monomethanesulfonate
Purity: ≥98% (HPLC)
Citations (2)
Literature (1)

Biological Activity for WIN 55,212-3 mesylate

Novel, low potency CB2 receptor silent antagonist and CB1 receptor partial inverse agonist. Competitively antagonizes effects of CP 55,940 (pA2 = 6.1) and SR 144528 (pEC50 = 5.3) at CB2 receptors and acts as a partial inverse agonist at CB1 receptors (pIC50 = 5.5). Displays modest activity at human melatonin MT1 and muscarinic M4 receptors, but is selective over several other GPCRs.

R-enantiomer also available.

Technical Data for WIN 55,212-3 mesylate

M. Wt 522.61
Formula C27H26N2O3.CH3SO3H
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 131543-25-4
PubChem ID 11613341
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.

Product Datasheets for WIN 55,212-3 mesylate

Certificate of Analysis / Product Datasheet
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References for WIN 55,212-3 mesylate

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

Savinainen et al (2005) Identification of WIN55212-3 as a competitive neutral antagonist of the human cannabinoid CB2 receptor. Br.J.Pharmacol. 145 636 PMID: 15852035

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2 Citations for WIN 55,212-3 mesylate

Citations are publications that use Tocris products. Selected citations for WIN 55,212-3 mesylate include:

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

Mereu et al (2003) Prenatal exposure to a cannabinoid agonist produces memory deficits linked to dysfunction in hippocampal long-term potentiation and glutamate release. Proc Natl Acad Sci U S A 100 4915 PMID: 12679519

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Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!

*Please note that Tocris will only send literature to established scientific business / institute addresses.

Cannabinoid Receptor Ligands Scientific Review

Cannabinoid Receptor Ligands Scientific Review

Written by Roger Pertwee, this review discusses compounds which affect the activity of the endocannabinoid system, focusing particularly on ligands that are most widely used as experimental tools and denotes compounds available from Tocris.