Cas no 104617-86-9 ((±)-Pramipexole)

(±)-Pramipexole is a synthetic aminobenzothiazole derivative that functions as a non-ergoline dopamine agonist. It exhibits high affinity for dopamine D2, D3, and D4 receptors, with preferential activity at the D3 subtype. This racemic mixture is primarily utilized in research applications to investigate dopaminergic pathways and receptor interactions. Its key advantages include well-characterized pharmacokinetics, stability under standard laboratory conditions, and consistent batch-to-batch purity, making it a reliable reference compound for neurological and pharmacological studies. The compound's solubility in aqueous and organic solvents further enhances its utility in in vitro and in vivo experimental models.
(±)-Pramipexole structure
(±)-Pramipexole structure
Product Name:(±)-Pramipexole
CAS No:104617-86-9
MF:C10H17N3S
MW:211.327080488205
MDL:MFCD21496628
CID:1145485
PubChem ID:4885
Update Time:2025-10-08

(±)-Pramipexole Chemical and Physical Properties

Names and Identifiers

    • N~6~-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine
    • 2,6-benzothiazolediamine, 4,5,6,7-tetrahydro-N~6~-propyl-
    • (±)-Pramipexole
    • Pramipexole
    • S(-)-2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole
    • (+/-)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine
    • (+/-)-Pramipexole
    • 2-amino-4,5,6,7-tetrahydro-6-n-propylaminobenzothiazole
    • 2-amino-6-n-propyl-amino-4,5,6,7-tetrahydrobenzothiazole
    • 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzthiazole
    • 2-Amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole
    • Pramipexole Impurity 9
    • A896190
    • Pramipexole Base
    • AKOS017258887
    • N*6*-Propyl-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine
    • (S)-N6-Propyl-4,5,6,7-tetrahydrobenzothiazole-2,6-diamine
    • DTXSID9091527
    • ALBB-027263
    • (+/-)-2-amino-6-propylamino-4,5,6,7-tetrahydrobenzthiazole
    • (+/-) 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole
    • DTXSID90274450
    • (+/-)-2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole
    • N6-Propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine
    • HMS3657G15
    • Pramipexole Impurity 21
    • CHEMBL76399
    • SY009549
    • SND 919
    • 6-N-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine
    • 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole
    • (R)-Pramipexole;R-(+)-Pramipexole;KNS-760704
    • EN300-296092
    • HMS3393A21
    • 104617-86-9
    • L000492
    • N6-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine
    • (+/-)-2-amino-6-(N-propylamino)-4,5,6,7-tetrahydrobenzothiazole
    • 2,6-benzothiazolediamine, 4,5,6,7-tetrahydro-N~6~-propyl-, dihydrochloride
    • NS00121232
    • N*6*-Propyl-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine (Pramipexole, PPX)
    • (S)-2-Amnio-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole
    • MFCD00869076
    • HMS3370D06
    • SCHEMBL195775
    • SB16953
    • BDBM50017550
    • (+/-)2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole
    • CHEBI:182913
    • ()-Pramipexole
    • (S)-2-amino-6-propylamino-4,5,6,7-tetrahydrobenzthiazole;(S)-2-amino-6-propylamino-4,5,6,7-tetrahydrobenzthiazole
    • A801038
    • (6R)-6-N-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine
    • MDL: MFCD21496628
    • Inchi: 1S/C10H17N3S/c1-2-5-12-7-3-4-8-9(6-7)14-10(11)13-8/h7,12H,2-6H2,1H3,(H2,11,13)
    • InChI Key: FASDKYOPVNHBLU-UHFFFAOYSA-N
    • SMILES: S1C(N)=NC2=C1CC(CC2)NCCC

Computed Properties

  • Exact Mass: 211.11400
  • Monoisotopic Mass: 211.11431873g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 3
  • Complexity: 188
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.9
  • Topological Polar Surface Area: 79.2?2

Experimental Properties

  • Density: 1.17±0.1 g/cm3 (20 oC 760 Torr),
  • Solubility: Slightly soluble (1.1 g/l) (25 o C),
  • PSA: 79.18000
  • LogP: 2.55430

(±)-Pramipexole Pricemore >>

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Additional information on (±)-Pramipexole

Introduction to (±)-Pramipexole and Its Significance in Modern Medicine

Chemical compounds play a pivotal role in the advancement of pharmaceutical sciences, particularly in the development of therapeutic agents that target neurological disorders. One such compound, (±)-Pramipexole, with the CAS number 104617-86-9, has emerged as a cornerstone in the treatment of movement disorders. This introduction delves into the compound's chemical properties, pharmacological mechanisms, clinical applications, and recent research findings that underscore its importance in contemporary medicine.

The molecular structure of (±)-Pramipexole is characterized by its ability to interact with dopamine receptors in the brain. Specifically, it is a selective agonist of D2-like dopamine receptors, which includes D2, D3, D4, and D5 receptors. This selectivity is crucial for its therapeutic efficacy and minimal side effects. The compound's chemical formula, C22H29N3O3, reflects its complex structure that contributes to its unique pharmacological profile.

Pramipexole, as a generic name, encompasses both enantiomers (±) of the compound. However, the racemic mixture is primarily used in clinical settings due to its balanced activity at dopamine receptors. The CAS number 104617-86-9 uniquely identifies this specific chemical entity, ensuring consistency in research and production. Understanding the nuances of (±)-Pramipexole's pharmacokinetics and pharmacodynamics is essential for optimizing its therapeutic use.

The primary clinical application of (±)-Pramipexole is in the management of Parkinson's disease (PD). It is particularly effective in alleviating symptoms such as tremors, rigidity, and bradykinesia by enhancing dopamine transmission in the brain. The compound's efficacy has been well-documented in numerous clinical trials and it remains a first-line treatment option for many patients with PD.

Recent research has expanded the therapeutic potential of (±)-Pramipexole beyond PD. Studies have explored its role in treating Restless Legs Syndrome (RLS), another neurological disorder characterized by involuntary leg movements and an urge to move them. The compound's ability to modulate dopamine levels has shown significant promise in alleviating RLS symptoms.

In addition to its neurological applications, ongoing research is investigating the potential benefits of (±)-Pramipexole in other medical conditions. For instance, preliminary studies suggest that it may have neuroprotective properties that could be beneficial in neurodegenerative diseases such as Alzheimer's disease. These findings highlight the compound's broad therapeutic spectrum and its potential for future medical applications.

The development of any pharmaceutical agent involves rigorous testing to ensure safety and efficacy. (±)-Pramipexole has undergone extensive clinical trials to evaluate its safety profile and therapeutic benefits. Common side effects include nausea, dizziness, and sleep disturbances, but these are generally manageable with appropriate dosing adjustments or supportive care.

The pharmacological mechanism of action of (±)-Pramipexole involves its high affinity for D2-like dopamine receptors. By binding to these receptors, it enhances dopaminergic neurotransmission in key brain regions involved in motor control. This mechanism is fundamental to its effectiveness in treating PD and RLS.

Advances in drug delivery systems have further enhanced the therapeutic potential of (±)-Pramipexole. Formulations such as extended-release tablets allow for sustained release of the compound, improving patient compliance and reducing side effects associated with peak concentrations.

The chemical synthesis of (±)-Pramipexole involves multi-step organic reactions that require precise control over reaction conditions and reagent selection. The synthesis process must adhere to stringent quality control measures to ensure the final product meets pharmaceutical standards.

Future research directions for (±)-Pramipexole include exploring its potential role in combination therapies for PD and other neurological disorders. Additionally, investigating new formulations that enhance bioavailability and reduce side effects could further improve patient outcomes.

In conclusion,(±)-Pramipexole, identified by the CAS number 104617-86-9, is a vital therapeutic agent with significant applications in managing movement disorders such as Parkinson's disease and Restless Legs Syndrome. Its selective action on dopamine receptors, coupled with ongoing research into its broader therapeutic potential, underscores its importance in modern medicine.

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