(+)-U-50488 hydrochlorideSelective κ-opioid agonist CAS# 114528-81-3 |
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Quality Control & MSDS
3D structure
Package In Stock
Number of papers citing our products
| Cas No. | 114528-81-3 | SDF | Download SDF |
| PubChem ID | 6918162 | Appearance | Powder |
| Formula | C19H27Cl3N2O | M.Wt | 405.79 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 100 mM in water and to 100 mM in DMSO | ||
| Chemical Name | 2-(3,4-dichlorophenyl)-N-methyl-N-[(1R,2R)-2-pyrrolidin-1-ylcyclohexyl]acetamide;hydrochloride | ||
| SMILES | CN(C1CCCCC1N2CCCC2)C(=O)CC3=CC(=C(C=C3)Cl)Cl.Cl | ||
| Standard InChIKey | KGMMGVIYOHGOKQ-JAXOOIEVSA-N | ||
| Standard InChI | InChI=1S/C19H26Cl2N2O.ClH/c1-22(19(24)13-14-8-9-15(20)16(21)12-14)17-6-2-3-7-18(17)23-10-4-5-11-23;/h8-9,12,17-18H,2-7,10-11,13H2,1H3;1H/t17-,18-;/m1./s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Less active enantiomer of (±)-U-50488. (-)-U-50488 hydrochloride also available. |
(+)-U-50488 hydrochloride Dilution Calculator
(+)-U-50488 hydrochloride Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.4643 mL | 12.3216 mL | 24.6433 mL | 49.2866 mL | 61.6082 mL |
| 5 mM | 0.4929 mL | 2.4643 mL | 4.9287 mL | 9.8573 mL | 12.3216 mL |
| 10 mM | 0.2464 mL | 1.2322 mL | 2.4643 mL | 4.9287 mL | 6.1608 mL |
| 50 mM | 0.0493 mL | 0.2464 mL | 0.4929 mL | 0.9857 mL | 1.2322 mL |
| 100 mM | 0.0246 mL | 0.1232 mL | 0.2464 mL | 0.4929 mL | 0.6161 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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(+)-U-50488 hydrochloride is a selective agonist for κ-opioid receptor [1].
The κ-opioid receptor (KOR) is a type of opioid receptor for opioid peptide dynorphin and controls addiction. Also, KOR plays an important role in stress, anxiety, anhedonia, depression and increased drug-seeking behavior.
(+)-U-50488 hydrochloride is a selective KOR agonist [1]. In isolated rat DRG neurons, U-50488 (0.3-40 μM) inhibited voltage-independent Ca2+ channel currents. In HeLa cells that didn’t express KOR, U-50488 (20 μM) blocked Ca2+ channels [2].
In rhesus monkeys, U-50488 exhibited potent antinociceptive activity and produced diuresis [1]. U-50488 enhanced contraction of the rabbit vas deferens induced by electrically with IC50 value of 26.5 nM. In mice, U-50488 impaired motor function with ED50 value of 15.3 mg/kg and reduced spontaneous activity [3]. In adult rats, U-50488 increased the threshold required to maintain self-stimulation responding, a depressive-like effect. While, males were significantly more sensitive than females to the threshold-increasing effects [4].
References:
[1]. Tang AH, Collins RJ. Behavioral effects of a novel kappa opioid analgesic, U-50488, in rats and rhesus monkeys. Psychopharmacology (Berl), 1985, 85(3): 309-314.
[2]. Hassan B, Ruiz-Velasco V. The κ-opioid receptor agonist U-50488 blocks Ca2+ channels in a voltage- and G protein-independent manner in sensory neurons. Reg Anesth Pain Med, 2013, 38(1): 21-27.
[3]. Lu SN, Ma SC, Zhang KG, et al. Comparison of pharmacological profile of selective kappa-opioid agonist K-II and U-50488. Yao Xue Xue Bao, 1991, 26(3): 171-174.
[4]. Russell SE, Rachlin AB, Smith KL, et al. Sex differences in sensitivity to the depressive-like effects of the kappa opioid receptor agonist U-50488 in rats. Biol Psychiatry, 2014, 76(3): 213-222.
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Synthesis and absolute configuration of optically pure enantiomers of a kappa-opioid receptor selective agonist.[Pubmed:2822490]
FEBS Lett. 1987 Nov 2;223(2):335-9.
The enantiomers of U50,488, ligands highly selective for kappa-opioid receptors, have been prepared by a refined procedure and their optical purity demonstrated. The absolute configuration of (+)-trans-2-pyrrolidinyl-N-methylcyclohexylamine, a chemically versatile intermediate for synthesis of analogs of kappa-opioid receptor ligands with defined chirality, has been determined to be 1S,2S by X-ray crystallographic analysis. This intermediate has been used to synthesize the optically pure U50,488 enantiomers with known absolute configuration.
