| Chemical & Physical Properties | |
|---|---|
| CAS Number | 131543-23-2 |
| Catalog No. | 2A-9052108 |
| Chinese Name | 甲磺酸西地那非 |
| Synonyms | WIN 55,212-2 (Mesylate); WIN 55,212-2; Lopac-W-102; MFCD00153882 |
| Molecular Formula | C27H26N2O3 · CH3SO3H |
| Molecular Weight | 522.61 |
| Purity | ≥98 (HPLC) |
| Boiling Point | 627.7ºC at 760 mmHg |
| Appearance | powder |
| Water Solubility | 0.1 M HCl: 0.25 mg/mL |
| Storage Condition | Keep the container sealed and stored in a cool, dr |
| Application | WIN 55,212-2 Mesylate is a potent cannabinoid receptor agonist with Ki values of 62.3 and 3.3 nM for human recombinant CB1 and CB2 receptors, respectively. |
| PubChem ID | 24278779 |
| MDL Number | MFCD00153882 |
| SMILES | CS(O)(=O)=O.Cc1c(C(=O)c2cccc3ccccc23)c4cccc5OC[C@@H](CN6CCOCC6)n1c45 |
| 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 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| MSDS | msds/52108_1_131543_23_2.pdf |
| Bioactivity | WIN 55,212-2 Mesylate is a potent aminoalkylindole cannabinoid (CB) receptor agonist with Kis of 62.3 and 3.3 nM for human recombinant CB1 and CB2 receptors, respectively. Related Catalog Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor Research Areas >> Neurological Disease Target Ki: 62.3 nM (human recombinant CB1), 3.3 nM (human recombinant CB2) In Vitro WIN 55,212-2 is more potent in CHO-CB2 cells than in CHO-CB1 cells by a factor of 6O. WIN 55,212-2 has no effect on arachidonic acid release in CHO-CB2 or control CHO cells. WIN 55,212-2 fails to stimulate any increase in intracellular Ca2+ up to 10 μM[1]. In primary cultures of rat cerebral cortex neurons, WIN 55,212-2 (0.01--100 nM) increases extracellular glutamate levels, displaying a bell-shaped concentration-response curve. The facilitatory effect of WIN 55,212-2 (1 nM) is fully counteracted by SR141716A (10 nM), by the replacement of the normal Krebs Ringer-bicarbonate buffer with a low Ca2+ medium (0.2 mM) and by the IP(3) receptor antagonist xestospongin C (1 μM)[2]. WIN 55,212-2 evokes CGRP release from TG neurons in vitro (EC50=26 μM) in a concentration- and calcium-dependent manner. WIN 55,212-2-2 neither inhibits capsaicin-evokes CGRP release nor does it inhibit forskolin-, isoproteranol- or prostaglandin E2-stimulated cAMP accumulation. WIN 55,212-2 significantly inhibits (EC50=1.7 μM) 50 mm K+-evoked CGRP release by approximately 70%. WIN 55,212-2 inhibition of 50 mm K+-evoked CGRP release is not reversed by antagonists of cannabinoid type 1 (CB1) receptor, but is mimicks in magnitude and potency (EC50=2.7 μM) by its cannabinoid-inactive enantiomer WIN 55,212-2-3[3]. In Vivo In the prefrontal cortex WIN 55,212-2 (0.1 and 1 mg/kg i.p.) increases dialysate glutamate levels from of the awake rat, while the lower (0.01 mg/kg) and the higher (2 mg/kg) doses are ineffective. Furthermore, the WIN 55,212-2 (0.1 mg/kg)- induced increase of dialysate glutamate levels is counteracted by pretreatment with the selective CB(1) receptor antagonist SR141716A (0.1 mg/kg, i.p.) and by the local perfusion with a low-calcium Ringer solution (Ca2+ 0.2 mM)[2]. WIN 55,212-2 (0.5, 1, 3, 5, 10 and 15 mg/kg, i.p.) does not alter the seizure threshold at low doses, while higher doses of the drug significantly increases the threshold in a dose-dependent manner. The anticonvulsant effect of WIN 55,212-2, which is observed with doses as high as 5 mg/kg, can be observed with doses as low as 0.5 mg/kg in groups pre-treated with 20 mg/kg of pioglitazone[4]. Animal Admin In experiment 1, different doses of WIN 55,212-2 (0.5, 1, 3, 5, 10 and 15 mg/kg) are injected 60 min prior to the determination of clonic seizure threshold induced by intravenous administration of PTZ solution. Control animals receive the same volume of the vehicle (1% aqueous solution of DMSO). The doses and time point are chosen on the basis of pilot studies. In experiment 2, in order to confirm the anticonvulsant effects of pioglitazone, different doses (10, 20, 40 and 80 mg/kg) are administered 4 h prior to PTZ in distinct groups of mice. The corresponding control groupreceive the appropriate vehicle (CMC 1%) at the same time point. In experiment 3, The additive anti epileptic effects of WIN 55,212-2 and pioglitazone are examined; mice receive acute administration of pioglitazone (10 or 20 mg/kg) 3 h before WIN 55,212-2 (0.5 or 1 mg/kg) and 4 h before PTZ. References [1]. Felder CC, et al. Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol Pharmacol. 1995 Sep;48(3):443-50. [2]. Ferraro 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. 2001 Aug;11(8):728-33. [3]. Price TJ, et al. Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons. Br J Pharmacol. 2004 May;142(2):257-66. [4]. Payandemehr B, et al. Involvement of PPAR receptors in the anticonvulsant effects of a cannabinoid agonist, WIN 55,212-2. Prog Neuropsychopharmacol Biol Psychiatry. 2015 Mar 3;57:140-5 Chemical & Physical Properties Boiling Point 627.7ºC at 760 mmHg Molecular Formula C28H30N2O6S Molecular Weight 522.613 Flash Point 333.4ºC Exact Mass 522.182434 PSA 106.45000 LogP 5.12230 Vapour Pressure 1.14E-15mmHg at 25°C InChIKey FSGCSTPOPBJYSX-VEIFNGETSA-N SMILES CS(=O)(=O)O.Cc1c(C(=O)c2cccc3ccccc23)c2cccc3c2n1C(CN1CCOCC1)CO3 Storage condition Store at +4°C Water Solubility 0.1 M HCl: 0.25 mg/mL |
| Use of | WIN 55,212-2 Mesylate is a potent aminoalkylindole cannabinoid (CB) receptor agonist with Kis of 62.3 and 3.3 nM for human recombinant CB1 and CB2 receptors, respectively. Properties Synonym More Synonyms Description WIN 55,212-2 Mesylate is a potent aminoalkylindole cannabinoid (CB) receptor agonist with Kis of 62.3 and 3.3 nM for human recombinant CB1 and CB2 receptors, respectively. Related Catalog Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor Research Areas >> Neurological Disease Ki: 62.3 nM (human recombinant CB1), 3.3 nM (human recombinant CB2) References [1]. Felder CC, et al. Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol Pharmacol. 1995 Sep;48(3):443-50. [2]. Ferraro 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. 2001 Aug;11(8):728-33. [4]. Payandemehr B, et al. Involvement of PPAR receptors in the anticonvulsant effects of a cannabinoid agonist, WIN 55,212-2. Prog Neuropsychopharmacol Biol Psychiatry. 2015 Mar 3;57:140-5 Chemical & Physical Properties Molecular Formula C28H30N2O6S Exact Mass 522.182434 PSA 106.45000 LogP 5.12230 InChIKey FSGCSTPOPBJYSX-VEIFNGETSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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