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(+)-WIN 55,212-2 (mesylate)

Item № 10009023
CAS № 131543-23-2
Purity ≥98%
product image
                (CAS 131543-23-2)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     5 mg $33.00 0.00
     10 mg $63.00 0.00
     25 mg $149.00 0.00
     50 mg $264.00 0.00

Pricing updated 2019-05-22. Prices are subject to change without notice.

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.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 is fully counteracted by rimonabant (Item No. 9000484) at a concentration of 10 nM, by decreasing Ca2+ concentrations below 0.2 mM, or by the IP3 receptor antagonist xestospongin C (Item No. 64950) 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.3

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Technical Information
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
Purity
≥98%
Formulation
A crystalline solid
λmax
219, 246, 330 nm
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
InChI=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

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
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Additional Information

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References & Product Citations
Product Description References

1. Felder, C.C., Joyce, K.E., Briley, E.M., et al. Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors Mol. Pharmacol. 48(3), 443-450 (1995).

2. Ferraro, L., Tomasini, M.C., Gessa, G.L., et al. The cannabinoid receptor agonist WIN 55,212-2 regulates glutamate transmission in rat cerebral cortex: An in vivo and in vitro study Cereb. Cortex 11(8), 728-733 (2001).

3. Price, T.J., Patwardhan, A., Akopian, A.N., et al. Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons Br. J. Pharmacol. 142(2), 257-266 (2004).

Product Citations

Roberto, D., Klotz, L.H., and Venkateswaran, V. Cannabinoid WIN 55,212-2 induces cell cycle arrest and apoptosis, and inhibits proliferation, migration, invasion, and tumor growth in prostate cancer in a cannabinoid-receptor 2 dependent manner Prostate (2018).

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