Pramipexole dihydrochloride

Names

[ Name ]:
Pramipexole dihydrochloride

[Synonym ]:
2,6-Benzothiazolediamine, 4,5,6,7-tetrahydro-N-propyl-, (6S)-, hydrochloride (1:2)
(6S)-4,5,6,7-Tetrahydro-N6-propyl-2,6-benzothiazolediamine Dihydrochloride
(S)-2-Amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole dihydrochloride
Pramipexole hydrochloride
Pramipexole dihydrochloride
MFCD00876894
(S)-Pramipexole Dihydrochloride
(6S)-N-Propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine dihydrochloride
(S)-N6-Propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine dihydrochloride
Pramipexole (dihydrochloride)

Biological Activity

[Description]:

Pramipexole 2Hcl is a partial/full D2S, D2L, D3, D4 receptor agonist with a Ki of 3.9, 2.2, 0.5 and 5.1 nM for D2S, D2L, D3, D4 receptor, respectively. IC50 Value: 3.9 nM(D2S); 2.2 nM(D2L); 0.5 nM(D3); 5.1 nM(D4)Target: Dopamine ReceptorPramipexole dihydrochloride is a dopamine receptor agonist with selectivity for the D3 receptor (Ki values are 3.9, 3.3, 0.5 and 3.9 nM for D2L, D2S, D3 and D4 receptors respectively). Pramipexole dihydrochloride exhibits negligable affinity for D1 and D5 receptors. 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 displays activity in the treatment of Parkinson's disease (PD) and restless legs syndrome (RLS).

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor

Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor

Research Areas >> Neurological Disease

[References]

[1]. Mierau J, Schneider FJ, Ensinger HA et al. Pramipexole binding and activation of cloned and expressed dopamine D2, D3 and D4 receptors. Eur J Pharmacol. 1995 Jun 23;290(1):29-36.

[2]. El-Mallakh RS, Penagaluri P, Kantamneni A et al. Long-term use of pramipexole in bipolar depression: a naturalistic retrospective chart review. Psychiatr Q. 2010 Sep;81(3):207-13.

[3]. Perez-Lloret S, Rey MV, Ratti L, Rascol O. Pramipexole for the treatment of early Parkinson's disease. Expert Rev Neurother. 2011 Jul;11(7):925-35.

[4]. Hametner EM, Seppi K, Poewe W. Pramipexole extended release in Parkinson's disease. Expert Rev Neurother. 2011 Sep;11(9):1229-34.

[5]. Hametner EM, Seppi K, Poewe W. Role and clinical utility of pramipexole extended release in the treatment of early Parkinson's disease. Clin Interv Aging. 2012;7:83-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
378ºC at 760 mmHg

[ Melting Point ]:
288-290ºC

[ Molecular Formula ]:
C₁₀H₁₉Cl₂N₃S

[ Molecular Weight ]:
284.249

[ Flash Point ]:
182.4ºC

[ Exact Mass ]:
283.067688

[ PSA ]:
79.18000

[ LogP ]:
4.15830

[ Vapour Pressure ]:
6.49E-06mmHg at 25°C

[ Storage condition ]:
Desiccate at RT

Safety Information

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Pramipexole reduces parkinsonian tremor induced by pilocarpine infusion in the rat striatum.

Pharmacol. Biochem. Behav. 131 , 1-5, (2015)

Pramipexole is widely prescribed for the treatment of Parkinson's disease. This dopamine (DA) receptor agonist has a higher affinity for D3 over D2 receptors. We compared the effect of pramipexole to ...

Alterations of BDNF and trkB mRNA expression in the 6-hydroxydopamine-induced model of preclinical stages of Parkinson's disease: an influence of chronic pramipexole in rats.

PLoS ONE 10(3) , e0117698, (2015)

Our recent study has indicated that a moderate lesion of the mesostriatal and mesolimbic pathways in rats, modelling preclinical stages of Parkinson's disease, induces a depressive-like behaviour whic...

De novo expression of dopamine D2 receptors on microglia after stroke.

J. Cereb. Blood Flow Metab. 35 , 1804-11, (2015)

Dopamine is the predominant catecholamine in the brain and functions as a neurotransmitter. Dopamine is also a potent immune modulator. In this study, we have characterized the expression of dopamine ...