WIN 55,212-2 MESYLATE
Synonym(s):(+)-WIN 55,212-2 mesylate - CAS 131543-23-2 - Calbiochem;(R)-(+)-[2,3-Dihydro-5-methyl-3[(4-morpholinyl)methyl]pyrrolo[1,2,3-de]-1,4-benzoxazinyl]-(1-naphthalenyl)methanone mesylate salt;WIN 552122 mesylate;WIN 55212-2 methanesulfonate
- CAS NO.:131543-23-2
- Empirical Formula: C28H30N2O6S
- Molecular Weight: 522.62
- MDL number: MFCD00153882
- EINECS: 1592732-453-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-03-22 14:56:24
What is WIN 55,212-2 MESYLATE?
Description
(+)-WIN 55,212-2 (mesylate) is a potent aminoalkylindole cannabinoid (CB) receptor agonist with Ki 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.
The Uses of WIN 55,212-2 MESYLATE
(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
Properties of WIN 55,212-2 MESYLATE
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. |
Safety information for WIN 55,212-2 MESYLATE
Computed Descriptors for WIN 55,212-2 MESYLATE
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| |
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