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A1237

Sigma-Aldrich

Pramipexole dihydrochloride

>98% (HPLC), 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:
104632-25-9
Molecular Weight:
284.25
MDL number:
MFCD00876894
UNSPSC Code:
51111800
PubChem Substance ID:
329770694
NACRES:
NA.77

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

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

Gene Information

human ... DRD2(1813) , DRD3(1814) , DRD4(1815)

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.

Application

Pramipexole dihydrochloride has been used as D2 receptor agonist in dopamine (DA)-depleted striatum slices.
Pramipexole dihydrochloride has been used as a D2-like DR (dopaminergic receptor) agonist in study associated with Parkinson′s disease. It has also been used as a D2/D3 receptor agonist to study risky decision-making in rats.

Biochem/physiol Actions

Pramipexole elicits neuroprotective role and may help in treating depression. It also has a potential to modulate limb movement and may be effective in treating restless legs syndrome.
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.

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H336

Hazard Classifications

Acute Tox. 4 Oral - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Esther Lara-González et al.
Neuroscience, 410, 76-96 (2019-05-13)
Parkinson's disease (PD) is a neurodegenerative illness presenting motor and non-motor symptoms due to the loss of dopaminergic terminals in basal ganglia, most importantly, the striatum. L-DOPA relieves many motor signs. Unfortunately, in the long term, L-DOPA use causes motor
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
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
William Winlow
Core evidence, 1(1), 35-42 (2005-01-01)
Restless legs syndrome (RLS) affects 5-15% of adults, but is often unrecognized and consequently misdiagnosed. The International Restless Legs Scale (IRLS) has been developed and validated to assess the severity of RLS. Currently, the most common treatment for RLS is
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