Pramipexole

Base Information

• Chemical Name: Pramipexole
• CAS No.: 104632-26-0
• Molecular Formula: C10H17N3S
• Molecular Weight: 211.331
• Hs Code.: 2934999090
• European Community (EC) Number: 600-593-1
• UNII: 83619PEU5T
• DSSTox Substance ID: DTXSID6023496
• Nikkaji Number: J419.937E
• Wikipedia: Pramipexole
• Wikidata: Q421304
• NCI Thesaurus Code: C66456
• RXCUI: 746741
• Pharos Ligand ID: BZUWXBF5CK5W
• Metabolomics Workbench ID: 42773
• ChEMBL ID: CHEMBL301265
• Mol file: 104632-26-0.mol

Synonyms:2 Amino 6 propylaminotetrahydrobenzothiazole;2-amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole;2-amino-6-propylaminotetrahydrobenzothiazole;4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazole-diamine;6,7-tetrahydro-N6-propyl-2,6-benzothiazolediamine dihydrochloride monohydrate;dexpramipexole;KNS 760704;KNS-760704;KNS760704;Mirapex;pramipexol;pramipexol dihydrobromide, (+-)-isomer;pramipexol dihydrochloride, (S)-isomer;pramipexol, (+-)-isomer;pramipexol, (R)-isomer;pramipexole;Pramipexole Dihydrochloride;Pramipexole Dihydrochloride Anhydrous;Pramipexole Hydrochloride Monohydrate;Sifrol;SND 919;SND 919CL2x;SND-919;SND-919CL2x;SND919CL2x

Chemical Property of Pramipexole

Chemical Property:

• Melting Point: 288-290 °C
• Boiling Point: 378 °C at 760 mmHg
• PKA: 9.47±0.20(Predicted)
• Flash Point: 182.4 °C
• PSA: 79.18000
• Density: 1.17 g/cm³
• LogP: 2.55430
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 211.11431873
• Heavy Atom Count: 14
• Complexity: 188

Purity/Quality:

99%min ^*data from raw suppliers

Pramipexole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiparkinson Agents
• Canonical SMILES: CCCNC1CCC2=C(C1)SC(=N2)N
• Isomeric SMILES: CCCN[C@H]1CCC2=C(C1)SC(=N2)N
• Recent ClinicalTrials: Long-term Efficacy of Pramipexole in Anhedonic Depression
• Recent EU Clinical Trials: PAX-D: Randomised placebo-controlled trial evaluating the efficacy and mechanism of pramipexole as add-on treatment for people with treatment resistant depression
• Recent NIPH Clinical Trials: An open-label, randomized controlled study evaluating the effectiveness of pramipexole extended-release tablets for tardive dystonia.
• Uses: (S)-Pramipexole enantiomer. A dopamine-D2-receptor agonist. Antiparkinsonian partial/full D2S, D2L, D3, D4 receptor agonist (S)-Pramipexole enantiomer. s disease (PD) and restless legs syndrome (RLS).[1] It is also sometimes used off-label as a treatment for cluster headache and to counteract the problems with sexual dysfunction experienced by some u sers of the selective serotonin reuptake inhibitor (SSRI) antidepressants.

Technology Process of Pramipexole

There total 24 articles about Pramipexole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole p-toluenesulfonic acid (943319-02-6) → pramipexole (104632-26-0)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 3h;

Reference yield: 98.0%

(S)?2?amino?6?propionamido?4,5,6,7?tetrahydrobenzothiazole (106006-84-2) → pramipexole (104632-26-0)

Guidance literature:

(S)?2?amino?6?propionamido?4,5,6,7?tetrahydrobenzothiazole; With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 15 ℃; for 2h;

With hydrogenchloride; sodium hydroxide; In tetrahydrofuran; water; ethyl acetate; at 0 - 20 ℃; for 1h;

Reference yield: 95.0%

1-Chloropropane (540-54-5) + (S)-4,5,6,7-tetrahydrobenzo[d]thiazol-2,6-diamine (106092-09-5,104617-49-4) → pramipexole (104632-26-0)

Guidance literature:

With NPs-Fe₃O₄(at)SiO₂(at)[PrMIM]PW; In acetonitrile; at 50 ℃; Reagent/catalyst;

DOI:10.1007/s11164-016-2741-2

upstream raw materials:

(S)?2?amino?6?propionamido?4,5,6,7?tetrahydrobenzothiazole

(6S,7S)-2-amino-7-hydroxy-6-(propylamino)-4,5,6,7-tetrahydrobenzothiazole

propyl bromide

(S)-4,5,6,7-tetrahydrobenzo[d]thiazol-2,6-diamine

Downstream raw materials:

(-)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-(biphenyl-4-yl)piperazin-1-yl)ethanone

(-)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-(2-methoxyphenyl)piperazin-1-yl)ethanone

(-)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-phenylpiperazin-1-yl)ethanone

(-)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethanone

Refernces

• 1、 -. "Preparation method of pramipexole". Paragraph 0025-0032. . Retrieved 2020/04/17.
• 2、 -. "Pramipexole related compound and preparation method and usage thereof". Paragraph 0048-0050. . Retrieved 2019/01/23.