WIN 55,212-2 MESYLATE Chemical Properties

storage temp. 

Store at +4°C

solubility 

0.1 M HCl: 0.25 mg/mL

form 

solid

color 

white to off-white

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.

InChIKey

FSGCSTPOPBJYSX-OZYVVJTJNA-N

SMILES

S(O)(=O)(=O)C.C(N1CCOCC1)[C@@H]1COC2=CC=CC3C(C(C4=CC=CC5=CC=CC=C45)=O)=C(C)N1C=32 |&1:12,r|

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

WIN 55,212-2 MESYLATE Usage And Synthesis

Description

(+)-WIN 55,212-2 (mesylate) is a potent aminoalkylindole cannabinoid (CB) receptor agonist with K_i values of 62.3 and 3.3 nM for human recombinant CB₁ and CB₂ receptors, respectively. In primary cultures of rat cerebral cortex neurons, (+)-WIN 55,212-2 (mesylate) (0.01-100 nM) increases extracellular glutamate levels, displaying a bell-shaped concentration-response curve. This effect is fully counteracted by rimonabant at a concentration of 10 nM, by decreasing Ca²⁺ concentrations below 0.2 mM, or by the IP₃ receptor antagonist xestospongin C at a concentration of 1 μM. (+)-WIN 55,212-2 (mesylate) induces release of the proinflammatory neuropeptide CGRP from trigeminal ganglion (TG) neurons in a calcium-dependent manner with an EC₅₀ value of 26 μM.

Uses

(R)-(+)-WIN 55,212-2 mesylate salt has been used as a high affinity cannabinoid agonist for intraperitoneal injection into rats to induce behavioural sensitization. It has also been used as a synthetic cannabinoid drug and cannabinoid receptor 1 (CNR1) agonist to treat Becn2+/? mice and wild-type (WT) littermate to analyze the levels of CNR1 in the brain.

General Description

WIN 55,212-2 is a member of the aminoalkylindole class of compounds.

Biological Activity

Nanomolar affinity cannabinoid receptor agonist (K i values are 62.3 and 3.3 nM at the human cloned CB 1 and CB 2 receptors respectively). Also available as part of the Cannabinoid Receptor Agonist Tocriset™ .

Biochem/physiol Actions

It is known to decrease the lipopolysaccharide mediated release of tumor necrosis factor- α and interleukin-1 in mice.

storage

Store at +4°C

References

1) Felder?et al. (1995),?Comparison of the pharmacology and signal transduction of the human cannabinoid CB1?and CB2receptors; Mol. Pharmacol.,?48?443 2) Herzberg?et al. (1997),?The analgesic effects of R(+)-WIN 55,212-2 mesylate, a high affinity cannabinoid agonist in a rat model of neuropathic pain; Neurosci. Lett.,?221?157 3) Bouaboula?et al. (1995),?Activation of mitogen-activated protein kinases by stimulation of the central cannabinoid receptor CB1; Biochem. J.,?312?637

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