131543-23-2

Basic information

• Product Name: WIN 55,212-2 MESYLATE
• Synonyms: R(+)-WIN 55,212-2 ,MESYLATE HIGH AFFINIT Y CANNABI;(R)-(+)-(2,3-Dihydro-5-methyl-3-(4-morpholinylmethyl)pyrrolo[1.2.3-de]-1,4-benzoxazin-6-yl)-1-naphthalenylmethanonemesy;212-2Mesylate;WIN55;(R)-(+)-WIN 55,212-2 mesylate salt;WIN 552122 mesylate, (R)-(+)-[2,3-Dihydro-5-methyl-3[(4-morpholinyl)methyl]pyrrolo[1,2,3-de]-1,4-benzoxazinyl]-(1-naphthalenyl)methanone mesylate salt;(R)-(+)-[2,3-Dihydro-5-methyl-3[(4-morpholinyl)methyl]pyrrolo[1,2,3-de]-1,4-benzoxazinyl]-(1-naphthalenyl)methanone mesylate salt;(R)-(5-Methyl-3-(MorpholinoMethyl)-2,3-dihydro-[1,4]oxazino[2,3,4-hi]indol-6-yl)(naphthalen-1-yl)Methanone
• CAS NO: 131543-23-2
• Molecular Formula: C28H30N2O6S
• Molecular Weight: 522.61
• EINECS: 1592732-453-0
• Product Categories: Cannabinoid receptor;Cannabinoid
• Mol File: 131543-23-2.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 627.7 °C at 760 mmHg
• Flash Point: 333.4 °C
• Appearance: white to off-white/solid
• Vapor Pressure: 1.14E-15mmHg at 25°C
• Storage Temp.: Store at +4°C
• Solubility: 0.1 M HCl: 0.25 mg/mL
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: WIN 55,212-2 MESYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: WIN 55,212-2 MESYLATE(131543-23-2)
• EPA Substance Registry System: WIN 55,212-2 MESYLATE(131543-23-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 131543-23-2(Hazardous Substances Data)

Usage

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.

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.

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

InChI:InChI=1/C27H26N2O3.CH4O3S/c1-18-25(27(30)22-9-4-7-19-6-2-3-8-21(19)22)23-10-5-11-24-26(23)29(18)20(17-32-24)16-28-12-14-31-15-13-28;1-5(2,3)4/h2-11,20H,12-17H2,1H3;1H3,(H,2,3,4)/t20-;/m1./s1