Ropinirole hydrochloride

Base Information

• Chemical Name: Ropinirole hydrochloride
• CAS No.: 91374-20-8
• Molecular Formula: C16H24N2O.ClH
• Molecular Weight: 296.84
• Hs Code.: 2933790002
• European Community (EC) Number: 635-615-9
• UNII: D7ZD41RZI9
• DSSTox Substance ID: DTXSID50238533
• Wikidata: Q27276228
• NCI Thesaurus Code: C47710
• RXCUI: 236553
• ChEMBL ID: CHEMBL1200411
• Mol file: 91374-20-8.mol

Synonyms:4-(2-(di-n-propylamino)ethyl)-2(3H)-indolone;Requip;ropinirol;ropinirole;ropinirole hydrochloride;SK and F 101468;SK and F-101,468;SKF 101468

Chemical Property of Ropinirole hydrochloride

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 6.01E-07mmHg at 25°C
• Melting Point: 241-243 °C
• Boiling Point: 410.5 °C at 760 mmHg
• Flash Point: 202 °C
• PSA: 32.34000
• LogP: 3.78570
• Storage Temp.: Room temp
• Solubility.: H2O: >10mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 296.1655411
• Heavy Atom Count: 20
• Complexity: 287

Purity/Quality:

99%, ^*data from raw suppliers

Ropinirole hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N, Xi
• Hazard Codes: Xn,N,Xi
• Statements: 22-50/53-36/38
• Safety Statements: 36-60-61-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCN(CCC)CCC1=C2CC(=O)NC2=CC=C1.Cl
• Recent ClinicalTrials: Open-Label Extension Study With REQUIP PR for Subjects From Study ROP111528
• Recent EU Clinical Trials: A Phase IV Acceptability and Feasibility Trial of the Effects of Medication on Memory in Idiopathic Nondementing Parkinson’s Disease.
• Recent NIPH Clinical Trials: Phase 1/2a Study of Ropinirole Hydrochloride Extended-Release Tablets in Patients with Amyotrophic Lateral Sclerosis (ALS)
• Description: ReQuip was launched in the UK as a monotherapy or in combination with low-dose levodopa for the treatment of early-stage idiopathic Parkinson's disease. An eight step (24% overall yield) synthesis from isochroman provides access to ropinirole. It is a non-ergot postsynaptic dopamine D2 agonist with activity in the extrapyramidal system. It has weak or no significant activity at α2-adrenergic, 5-HT2 receptors and is inactive at 5-HT1, benzodiazepine, GABA, α1 and β adrenoreceptors. Thus it has essentially no CNS side effects, fewer dyskinesias and on-off fluctuations. In animals, it was able to reverse all motor deficits induced by MPTP. Tolerance is not developed and ropinirole has similar postsynaptic potency to apomorphine but with significantly less stereotyped behavior. Ropinirole is a potent dopamine D2 receptor agonist (Ki = 29 nM in a radioligand binding assay). It is selective for D2 over D1 dopamine receptors (Ki = >100,000 nM) as well as a panel of adrenergic, serotonin, benzodiazepine, and GABA receptors (IC50s = >9,000 nM). Ropinirole reduces spontaneous locomotor activity in mice at doses less than 50 mg/kg but increases it at a dose of 100 mg/kg. It also induces contralateral asymmetry in an open field test in 6-OHDA-lesioned mice. Ropinirole (0.01-1 mg/kg) reverses locomotor deficits and restores interest in novel stimuli in a marmoset model of Parkinson''s disease induced by MPTP. Formulations containing ropinirole have been used for the treatment of Parkinson''s disease motor dysfunction.
• Uses: An antiparkinsonian agent. A selective dopamine D2-receptor agonist antiparkinsonian;non-ergoline D2, D3, and D4 dopamine receptor agonist with highest affinity for D3

Technology Process of Ropinirole hydrochloride

There total 32 articles about Ropinirole hydrochloride 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%

propionic acid (802294-64-0,79-09-4) + N-Despropylropinirole → ropinirole hydrochloride (91374-20-8)

Guidance literature:

propionic acid; With sodium tetrahydroborate; In toluene; at 0 - 5 ℃;

N-Despropylropinirole; With sodium tetrahydroborate; In toluene; at 25 - 80 ℃; for 3h;

With hydrogenchloride; In water; isopropyl alcohol;

DOI:10.1080/00397911.2017.1396613

Reference yield: 87.2%

<2-nitro-6-<2-(N,N-di-n-propylamino)ethyl>phenyl>acetic acid hydrochloride (91374-25-3) → ropinirole hydrochloride (91374-20-8)

Guidance literature:

<2-nitro-6-<2-(N,N-di-n-propylamino)ethyl>phenyl>acetic acid hydrochloride; With hydrogen; palladium 10% on activated carbon; In water; at 30 - 35 ℃; for 8h; under 2942.29 Torr;

With sodium hydroxide; In water; pH=10 - 11;

With hydrogenchloride; In ethanol; at 0 - 20 ℃; for 0.5 - 0.666667h; pH=2.0 - 3.0;

Reference yield: 87.0%

di-n-propylamine (142-84-7) + 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl-4-methylbenzene-1-sulfonate (139122-20-6) → ropinirole hydrochloride (91374-20-8)

Guidance literature:

In water; at 80 ℃; for 5h;

upstream raw materials:

Ropinirole

di-n-propylamine

4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one

4-(2'-aminoethyl)-1,3-dihydro-2H-indol-2-one hydrochloride

Downstream raw materials:

Ropinirole

4-(2-dipropylaminoethyl)-1-hydroxy-1,3-dihydroindol-2-one

4-(2-dipropylaminoethyl)-1H-indol-2,3-dione

2-nitro-6-<2-(di-n-propylamino)ethyl>phenylacetic acid

Refernces

• 1、 Quadri, Syed Aziz Imam,Das, Tonmoy C.,Jadhav, Shivaji,Farooqui, Mazahar. "Efficient synthesis of tertiary amine by direct N-alkylation of secondary amine with carboxylic acid using Ni (0) encat catalyst". supporting information. p. 267 - 277. Retrieved 2018/01/08.
• 2、 Yousuf, Zeshan,Richards, Andrew K.,Dwyer, Andrew N.,Linclau, Bruno,Harrowven, David C.. "The development of a short route to the API ropinirole hydrochloride". . p. 10532 - 10539. Retrieved 2015/11/10.