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(+)-WIN 55,212-2 (mesylate)
Cayman Chemical Item Number 10009023
Description
(+)-WIN 55,212-2 (mesylate) is a potent aminoalkylindole cannabinoid (CB) receptor agonist with a Ki of 62.3 and 3.3 nM for human recombinant CB1 and CB2 receptors, respectively.1↗ 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.2↗ This effect at a concentration of 1 nM was fully counteracted by SR141716A (10 nM), by decreasing Ca2+ concentrations below 0.2 mM, and by the IP3 receptor antagonist xestospongin C at 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 of 26 µM.3↗ In addition, (+)-WIN 55,212-2 (mesylate)-evoked CGRP release is not stereospecific, as the CB receptor-inactive enantiomer (+)-WIN 55,212-3 also stimulates CGRP exocytosis.
Formal Name [(3R)-2,3-dihydro-5-methyl-3-(4-morpholinylmethyl)pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenyl-methanone, monomethanesulfonate
CAS Number 131543-23-2
Molecular Formula C27H26N2O3 • CH3SO3H
Formula Weight 522.6
Formulation A crystalline solid
Purity ≥98%
λmax 219, 246, 330 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES O=C(C1=CC=CC2=C1C=CC=C2)C3=C(C)N(C4=C3C=CC=C4OC5)[C@@H]5CN6CCOCC6.CS(=O)(O)=O
InCHI Code 1S/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
InCHI Key FSGCSTPOPBJYSX-VEIFNGETSA-N |