| Identification | Back Directory | [Name]
Pramipexole Impurity 16 | [CAS]
104632-27-1 | [Synonyms]
RPPX
Kns 760704
Snd 919cl2x
Dexpramipexole HCl
Pramipexole R-Isomer
PraMipexole IMpurity D
Pramipexole impurity D CRS
KNS-760704 dihydrochloride
Pramipexole EP Impurity D DiHCl
(R)-Pramipexole (hydrochloride)
DexpraMipexole (dihydrochloride)
Pramipexole dihydrochloride impurity IV
Pramipexole Dihydrochloride Hydrate IMP
Pramipexole Dihydrochloride Hydrate Impurity
Dexpramipexole dihydrochloride
((R)-Pramipexole
Pramipexole EP Impurity D ((R)-Pramipexole diHCl)
(R)-PRAMIPEXOLE DIHYDROCHLORIDE; KNS 760704; SND 919CL2X
(R)-4,5,6,7-Tetrahydro-6-(propylamino)-benzothiazole-2-amine dihydrochloride
(R)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine dihydrochloride
2,6-Benzothiazolediamine, 4,5,6,7-tetrahydro-N6-propyl-, dihydrochloride, (R)-
(6R)-6-N-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine,dihydrochloride
(R)-2-Amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole dihydrochloride // (R)-Pramipexole dihydrochloride
Pramipexole Related Compound D ((R)-2-Amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole dihydro (1553815) | [Molecular Formula]
C10H19Cl2N3S | [MDL Number]
MFCD09031317 | [MOL File]
104632-27-1.mol | [Molecular Weight]
284.249 |
| Chemical Properties | Back Directory | [storage temp. ]
-20°C | [solubility ]
H2O: >15mg/mL | [form ]
powder | [color ]
white to beige | [Optical Rotation]
[α]/D 60 to 70°, c = 1 in methanol |
| Hazard Information | Back Directory | [Description]
Pramipexole (Item No. 11981) is an agonist of dopamine receptors that has applications in Parkinson’s disease and other disorders. Pramipexole is usually available as a mixture of enantiomers, with the majority of the dopamine receptor-dependent activity resulting from the (S) form. (R)-Pramipexole is an enantiomer of pramipexole that is ~100-fold less active than the (S) form as a dopamine receptor agonist. For this reason, it can be used as a negative control for the (S) form in the study of dopamine receptors. Both isoforms are antioxidants that target mitochondria to prevent apoptosis. This cytoprotective effect of (R)-pramipexole, without dopaminergic side effects, suggests utility in amyotrophic lateral sclerosis. | [Uses]
(R)-Pramipexole Dihydrochloride (Pramipexole EP Impurity D; Pramipexole BP Impurity D; Pramipexole USP Related Compound D) is the opposite enantiomer of Pramipexole (P700755), a dopamine-D2-receptor agonist. Dexpramipexole is a low-molecular-weight, water-soluble, orally bioavailable, renally excreted compound with linear pharmacokinetics. | [Uses]
These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements. Pramipexole may be used as a secondary pharma standard for the determination of the analyte in pharmaceutical formulations using reversed-phase high-performance liquid chromatography and ultraviolet spectrophotometry technique. | [General Description]
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. Pramipexole Related Compound D is a pharmaceutical impurity of pramipexole. Pramipexole is a non-ergot dopamine receptor agonist, widely used in the treatment of Parkinson′s disease. | [Biochem/physiol Actions]
R-(+)-Pramipexole is a neuroprotective agent; weak non-ergoline dopamine agonist. R-(+)-Pramipexole has been found to have neuroprotective effects and is being investigated for treatment of ALS. It reduces mitochondrial reactive oxygen species (ROS) production, inhibits the activation of apoptotic pathways, and increase cell survival in response to a variety of neurotoxins and β-amyloid neurotoxicity. Compared to the S-(-) isomer, R-(+)-Pramipexole has much lower dopamine agonist activity. | [Synthesis]
The general procedure for the synthesis of (R)-N6-propyl-4,5,6,7-tetrahydrobenzothiazole-2,6-diamine dihydrochloride using (R)-N-(2-amino-4,5,6,7-tetrahydrobenzothiazol-6-yl)-propanamide as starting material was as follows: under nitrogen protection, (R)-N-(2-amino-4,5,6,7-tetrahydrobenzothiazol-6-yl)-propanamide (10 g, 33.43 mmol) with dichloromethane (100 mL) was added to a round bottom flask, stirred for 10-15 min and then cooled to 0-5 °C. Subsequently, trimethylsilyl chloride (5.1 mL, 40.12 mmol) was slowly added over 10-15 minutes and stirring was continued at the same temperature for 10-15 minutes. A tetrahydrofuran solution of lithium aluminum hydride (19.5 mL, 46.81 mmol) was added dropwise at -10°C to 0°C. After dropwise addition, the reaction mixture was kept at 0-10 °C and stirring was continued for 1-2 hours. Upon completion of the reaction (monitored by thin layer chromatography), 2M sodium hydroxide solution (30 mL) was slowly added dropwise to quench the reaction and stirred for 10-15 minutes. After separating the aqueous and organic layers, the target compound was extracted from the aqueous layer with dichloromethane (50.0 mL). The organic layers were combined and washed with 20% NaCl solution. Finally, the dichloromethane layer was concentrated to give a crude product which was dissolved in isopropanol (50.0 mL). | [References]
[1] Tetrahedron Letters, 2013, vol. 54, # 36, p. 4908 - 4913 |
|
| Company Name: |
BOC Sciences
|
| Tel: |
1-631-485-4226; 16314854226 |
| Website: |
https://www.bocsci.com |
|