Rotigotine Hydrochloride (N-0437; N-0923) is a potent, non-selective and dopamine receptor full agonist, used in the treatment of Parkinson's disease and restless legs syndrome. Rotigotine is an agonist of the dopamine D2 and D3 receptors, with corresponding Ki values of 13 and 0.71 nM for D2 and D3. Additionally, rotigotine exhibits a strong affinity for adrenergic α2B and 5-HT1A receptors.
Physicochemical Properties
| Molecular Formula | C19H26CLNOS |
| Molecular Weight | 351.93 |
| Exact Mass | 351.142 |
| Elemental Analysis | C, 64.84; H, 7.45; Cl, 10.07; N, 3.98; O, 4.55; S, 9.11 |
| CAS # | 125572-93-2 |
| Related CAS # | Rotigotine; 99755-59-6; Rotigotine-d7 hydrochloride |
| PubChem CID | 180335 |
| Appearance | White to off-white solid powder |
| Boiling Point | 470.1ºC at 760 mmHg |
| Melting Point | 186.5-187.5ºC |
| Flash Point | 238.1ºC |
| Vapour Pressure | 1.84E-09mmHg at 25°C |
| LogP | 5.067 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 23 |
| Complexity | 337 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | OC1=C2CC[C@@H](CC2=CC=C1)N(CCC3=CC=CS3)CCC.[H]Cl |
| InChi Key | CEXBONHIOKGWNU-NTISSMGPSA-N |
| InChi Code | InChI=1S/C19H25NOS.ClH/c1-2-11-20(12-10-17-6-4-13-22-17)16-8-9-18-15(14-16)5-3-7-19(18)21;/h3-7,13,16,21H,2,8-12,14H2,1H3;1H/t16-;/m0./s1 |
| Chemical Name | (6S)-6-[propyl(2-thiophen-2-ylethyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol;hydrochloride |
| Synonyms | Rotigotine Hydrochloride; N 0923; N-0923; N-0924; Rotigotine HCl; Neupro |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | D3 Receptor ( Ki = 0.71 nM ); D2 Receptor ( Ki = 4-15 nM ); D5 Receptor ( Ki = 4-15 nM ); D4 Receptor ( Ki = 4-15 nM ); D1 Receptor ( Ki = 83 nM ); α1A ( Ki = 176 nM ); α1B ( IC50 = 273 nM ); α2A ( IC50 = 338 nM ); α2B ( IC50 = 27 nM ); 5-HT1A Receptor ( Ki = 30 nM ); 5-HT7 Receptor ( Ki = 86 nM ) | |
| ln Vitro |
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| ln Vivo |
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| Enzyme Assay | In 96-well polypropylene tubes, binding assays are carried out with a final volume of 2 mL for D1 and D4 membranes and 1 mL for D2, D3, and D5 membranes. These tubes contain the following materials: 50 μL radioligand, 10 μL drug/buffer/non-specific binding, buffer (final concentration 50 mM Tris-HCl pH 7.4, MgCl2 2 mM), and membranes (5 μg protein for D2 and D3 and 25 μg protein for D1 and D5). Rapid vacuum filtration through A/C glass fiber filters presoaked in 0.1% polyethylenimine is used to determine bound radioligand after 120 minutes of incubation at 25°C. Liquid scintillation counting is used to determine the retained radioactivity after the filters are four times cleaned with 2 mL of ice-cold ishing buffer (Tris-HCl 50 mM, pH 7.4 at 4°C). | |
| Animal Protocol |
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| References |
[1]. Rotigotine is a potent agonist at dopamine D1 receptors as well as at dopamine D2 and D3 receptors. Br J Pharmacol. 2015 Feb;172(4):1124-35. [2]. The in vitro receptor profile of rotigotine: a new agent for the treatment of Parkinson's disease. Naunyn Schmiedebergs Arch Pharmacol. 2009 Jan;379(1):73-86. [3]. In vivo dopamine agonist properties of rotigotine: Role of D1 and D2 receptors. Eur J Pharmacol. 2016 Oct 5;788:183-91. [4]. Neuroprotective effect of rotigotine against complex I inhibitors, MPP+ and rotenone, in primary mesencephalic cell culture. Folia Neuropathol. 2014;52(2):179-86. |
Solubility Data
| Solubility (In Vitro) |
DMSO: ≥ 50 mg/mL (~142.1 mM) H2O: ~4.8 mg/mL (~13.5 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.10 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.10 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (7.10 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8415 mL | 14.2074 mL | 28.4147 mL | |
| 5 mM | 0.5683 mL | 2.8415 mL | 5.6829 mL | |
| 10 mM | 0.2841 mL | 1.4207 mL | 2.8415 mL |