3D Mol Similar

Ropinirole hydrochloride

: Iupac Name：4-[2-(dipropylamino)ethyl]-1,3-dihydroindol-2-one;hydrochloride; CAS No.: 91374-20-8; Molecular Weight：296.84; Modify Date.: 2022-11-30 11:19

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1. Names and Identifiers

: 1.1 Name; Ropinirole hydrochloride; 1.2 Synonyms; 1,3-dihydro-4-(2-(dipropylamino)ethyl)-2h-indol-2-onemonohydrochloride 1,3-dihydro-4-(2-(dipropylamino)ethyl)-2h-indol-2-onmonohydrochloride 4-(2-(dipropylamino)ethyl)-2-indolinonemonohydrochloride 4-[2-(Di-n-propylamino)ethyl]-2(3H)-indolone Hydrochloride 4-[2-(Dipropylamino)ethyl]-1,3-dihydro-2H-indol-2-one Hydrochloride Requi REQUIP Ropinirol hydrochloride; View all

1.3 CAS No.: 91374-20-8

1.4 CID: 68727

1.5 EINECS(EC#): 635-615-9

1.6 Molecular Formula: C16H25ClN2O (isomer)

1.7 Inchi: InChI=1S/C16H24N2O.ClH/c1-3-9-18(10-4-2)11-8-13-6-5-7-15-14(13)12-16(19)17-15;/h5-7H,3-4,8-12H2,1-2H3,(H,17,19);1H

1.8 InChIkey: XDXHAEQXIBQUEZ-UHFFFAOYSA-N

1.9 Canonical Smiles: Cl.CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2

1.10 Isomers Smiles: CCCN(CCC)CCC1=C2CC(=O)NC2=CC=C1.Cl

2. Properties

2.1 Melting point: 241-243°C

2.1 StorageTemp: 2-8°C

3. Safety and Handling

3.1 Hazard Codes: Xn,N,Xi

3.1 Risk Statements: 22-50/53-36/38

3.1 Safety Statements: 36-60-61-37/39-26

3.1 RIDADR: UN 3077 9/PG 3

3.1 WGK Germany: 3

3.1 RTECS: NM3288250

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H400 Very toxic to aquatic life
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

5. Synthesis Route

91374-20-8Total: 9 Synthesis Route

91374-25-3 12 Suppliers

91374-20-8 194 Suppliers

Literatures:
IND-SWIFT LABORATORIES LIMITED Patent: WO2008/84499 A1, 2008 ; Location in patent: Page/Page column 8 ;
Yield: ~89%

91374-21-9 112 Suppliers

91374-20-8 194 Suppliers

Literatures:
WO2005/40115 A1, ; Page/Page column 6 ;
Yield: null

863436-07-1

91374-20-8 194 Suppliers

Literatures:
Helm AG; CF Pharma Gyogyszergyarto Kft. Patent: EP1568689 A1, 2005 ; Location in patent: Page/Page column 7 ;
Yield: ~40%

View all

6. Precursor and Product

precursor:

142-84-7

120427-95-4

920986-68-1

139122-20-6

91374-21-9

139122-17-1

139122-18-2

91374-25-3

863436-07-1

120427-96-5

product :

91374-21-9

7. Other Information

7.0 Target: Value

7.1 D2 receptor: 29 nM(Ki)

7.2 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.

7.3 Description: Ropinirole is a potent dopamine D₂ receptor agonist (K_i = 29 nM in a radioligand binding assay). It is selective for D₂ over D₁ dopamine receptors (K_i = >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.

7.4 Chemical Properties: Off-White Solid

7.5 Originator: SmithKline Beecham (UK)

7.6 Uses: An antiparkinsonian agent. A selective dopamine D2-receptor agonist

7.7 Uses: antiparkinsonian;non-ergoline D2, D3, and D4 dopamine receptor agonist with highest affinity for D3

7.8 Brand name: Requip (GlaxoSmithKline).

7.9 General Description: Ropinirole hydrochloride,4-(2-(dipropylamino)ethyl)indolin-2-one hydrochloride(Requip), is a white to pale greenish yellow powder that isvery soluble in water. Ropinirole is rapidly absorbed afteroral administration with maximal plasma concentrationsgenerally reached after about 1.5 hours, and the eliminationhalf-life appears to be approximately 3 hours. Ropinirole isalso rapidly and extensively distributed from the vascularcompartment and shows low plasma protein binding that isindependent of its plasma concentration. This drug iscleared by metabolism in the liver, with only 10% being excretedunchanged. The main metabolite of ropinirole is theN-despropyl metabolite. The glucuronide of this metaboliteand the carboxylic acid metabolite, 4-carboxymethylindolin-2-one, account only for 10% of the administered dose.None of the metabolites is pharmacologically active, and theexcretion of ropinirole-derived products is mainly via theurine. The main CYP450 isozyme involved in the metabolismof ropinirole is CYP1A2. Inhibitors or inducers ofthis enzyme have been shown to alter the clearance ofropinirole.Ropinirole is believed to act as an agonist atpostsynaptic D₂ receptors. Ropinirole is indicated for thetreatment of the signs and symptoms of idiopathic PD andmoderate to severe primary RLS.; View all

7.10 Biological Activity: Selective D 2 -like receptor agonist (D 3 > D 2 > D 4 ). Causes biphasic spontaneous locomotor activity and contralateral circling in 6-OHDA-lesioned mice. Displays antiParkinsonian activity.

7.11 Biochem/physiol Actions: An agonist at the D2 and D3 dopamine receptor subtypes, binding with higher affinity to D3 than to D2 or D4. It has negligible effect on D1-receptors. It has medium in vitro affinity to opioid receptors. Ropinirole is said to have virtually no affinity to 5-HT1, 5-HT2, benzodiazepine, GABA, muscarinic, α1-, α2-, and β-adrenoreceptors. Used as antiparkinsonian drug.

8. Computational chemical data

Molecular Weight: 296.84g/mol
Molecular Formula: C₁₆H₂₅ClN₂O
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 296.1655411
Monoisotopic Mass: 296.1655411
Complexity: 287
Rotatable Bond Count: 7
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 32.3
Heavy Atom Count: 20
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB7IAAEAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgBAAAAHgAQAAAADAjBmAQywIPAAACIAiVSUACCAAAhAgAIiAEIZIgIIDLAlZGEIAhglADIyAcciICOgAAAQAASAAAAAACAACQAAAAAAAAAAA==

9. Question & Answer

What is the mechanism of action of Ropinirole hydrochloride and how is it used? Jan 11 2021
Ropinirole hydrochloride is a potent selective non-ergoline dopamine D2 receptor agonist that directly stimulates dopamine receptors in the striatum. It improves motor slowness, stiffness, tremors, an..

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