Pramipexole dihydrochloride (A1237) is described with the synonym (S)-2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole dihydrochloride, indicating it is the S (L) enantiomer. The optical rotation is measured and can be found in the Certificate of Analysis (COA) for this product. The specification for this product is between -60° and -70°, which is consistent with the S (L) enantiomer of pramipexole.
A1237
Pramipexole dihydrochloride
>98% (HPLC), Dopamine D2 and D3 receptor agonist, powder
Synonym(s):
(S)-2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole dihydrochloride, PPX dihydrochloride
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About This Item
Empirical Formula (Hill Notation):
C10H17N3S · 2HCl
CAS Number:
Molecular Weight:
284.25
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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Product Name
Pramipexole dihydrochloride, >98% (HPLC), powder
SMILES string
Cl.Cl.CCCN[C@H]1CCc2nc(N)sc2C1
InChI
1S/C10H17N3S.2ClH/c1-2-5-12-7-3-4-8-9(6-7)14-10(11)13-8;;/h7,12H,2-6H2,1H3,(H2,11,13);2*1H/t7-;;/m0../s1
InChI key
QMNWXHSYPXQFSK-KLXURFKVSA-N
assay
>98% (HPLC)
form
powder
storage condition
desiccated
color
white to off-white
solubility
H2O: >20 mg/mL
originator
Boehringer Ingelheim
storage temp.
2-8°C
Quality Level
Gene Information
human ... DRD2(1813), DRD3(1814), DRD4(1815)
Related Categories
1 of 4
This Item | |||
|---|---|---|---|
| form powder | form - | form powder | form powder |
| assay >98% (HPLC) | assay - | assay - | assay ≥98% (HPLC) |
| Quality Level 100 | Quality Level 300 | Quality Level 200 | Quality Level 100 |
| storage temp. 2-8°C | storage temp. 2-30°C | storage temp. 2-8°C | storage temp. 2-8°C |
| storage condition desiccated | storage condition - | storage condition - | storage condition desiccated |
| solubility H2O: >20 mg/mL | solubility - | solubility alcohol: 20 mg/mL, H2O: soluble | solubility H2O: 20 mg/mL, clear |
General description
Pramipexole belongs to non-ergoline class and is derived from benzothiazole. It has strong affinity for D2 and D3 receptors (dopamine receptors) compared to other ergoline-derived drugs. However, it does not associate with non-dopamine receptors, for instance adrenergic and serotonin receptors.[1]
Application
Pramipexole dihydrochloride has been used as D2 receptor agonist in dopamine (DA)-depleted striatum slices.[2]
Biochem/physiol Actions
Pramipexole dihydrochloride monohydrate is a dopamine agonist active at D3 and D2 receptor subtypes.
Pramipexole elicits neuroprotective role and may help in treating depression.[5] It also has a potential to modulate limb movement and may be effective in treating restless legs syndrome.[6]
Pramipexole is a dopamine agonist active at D3 and D2 receptor subtypes. Pramipexole has been found to have neuroprotective effects independent of its dopamine receptor agonism. It reduces mitochondrial reactive oxygen species (ROS) production and inhibits the activation of apoptotic pathways.
Pramipexole is a therapeutic agent for Parkinson′s disease and restless leg syndrome. It also exhibits antidepressant responses in patients suffering from MDD (major depressive disorder) and bipolar depression.[7]
Features and Benefits
This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Dopamine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Boehringer Ingelheim. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - STOT SE 3
target_organs
Central nervous system
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
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Natasa Kustrimovic et al.
Scientific reports, 6, 33738-33738 (2016-09-23)
Parkinson's disease (PD) is characterized by loss of dopaminergic neurons in substantia nigra pars compacta, α-synuclein (α-syn)-rich intraneuronal inclusions (Lewy bodies), and microglial activation. Emerging evidence suggests that CD4+ T lymphocytes contribute to neuroinflammation in PD. Since the mainstay of
Haritz Jiménez-Urbieta et al.
Neurobiology of aging, 75, 126-135 (2018-12-21)
Treatment with dopaminergic agonists such as pramipexole (PPX) contributes to the development of impulse control disorders (ICDs) in patients with Parkinson's disease (PD). As such, animal models of abnormal impulse control in PD are needed to better study the pathophysiology
Jose A Franco-Chaves et al.
Journal of affective disorders, 149(1-3), 319-325 (2013-03-23)
Antidepressants that act on two or more amine neurotransmitters may confer higher remission rates when first-line agents affecting a single neurotransmitter have failed. Pramipexole, a dopamine agonist, has antidepressant effects in patients with major depressive disorder (MDD). This pilot study
Serdar Tort et al.
International journal of pharmaceutics, 579, 119164-119164 (2020-02-23)
Floating gastro-retentive delivery systems can prolong the gastric residence providing sustained drug release. In this study, we report on self-inflating effervescence-based electrospun nanofiber membranes embedding polyethylene oxide/sodium bicarbonate cast films. In this system, sodium bicarbonate results in an effervescence effect
Clinical Experience With High-Dosage Pramipexole in Patients With Treatment-Resistant Depressive Episodes in Unipolar and Bipolar Depression.
Jan Fawcett et al.
The American journal of psychiatry, 173(2), 107-111 (2016-02-06)
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Is this pramipexole the pure L enantiomer? Or a racemic mixture of L and R? If pure enantiomer: 1. how was this determined and 2. are the data supporting this available?
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