Ropinirole D3 Hydrochloride

Cat. No.: B2978499

CAS No.: 1329611-00-8

M. Wt: 299.86

InChI Key: XDXHAEQXIBQUEZ-NIIDSAIPSA-N

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Overview

1. Description

8. Comparison with similar compounds

2. Scientific research applications

9. Properties

3. Mechanism of action

10. Synthesis routes and methods I

4. Safety and hazards

11. Synthesis routes and methods II

5. Future directions

12. Synthesis routes and methods III

6. Preparation methods

13. Disclaimer

7. Chemical reactions analysis

Description

Ropinirole D3 Hydrochloride is a deuterated form of Ropinirole Hydrochloride, a non-ergoline dopamine agonist. It is primarily used in the treatment of Parkinson’s disease and Restless Legs Syndrome. The deuterated version, this compound, contains deuterium atoms, which can enhance the pharmacokinetic properties of the compound, potentially leading to improved efficacy and reduced side effects .

Scientific Research Applications

Ropinirole D3 Hydrochloride has several scientific research applications, including:

Chemistry: Used as a reference standard in analytical chemistry to study the pharmacokinetics and metabolism of Ropinirole.

Biology: Employed in biological studies to understand the effects of deuterium substitution on biological systems.

Medicine: Investigated for its potential to improve the treatment of Parkinson’s disease and Restless Legs Syndrome by enhancing the pharmacokinetic properties of Ropinirole.

Industry: Utilized in the pharmaceutical industry for the development of more effective and safer medications.

Mechanism of Action

Ropinirole has a high relative in vitro specificity and full intrinsic activity at the D2 and D3 dopamine receptor subtypes . It has moderate in vitro affinity for opioid receptors. Ropinirole and its metabolites have negligible in vitro affinity for dopamine D1, 5-HT1, 5-HT2, benzodiazepine, GABA, muscarinic, alpha1-, alpha2-, and beta-adrenoreceptors.

Safety and Hazards

Ropinirole Hydrochloride is toxic and contains a pharmaceutically active ingredient. Handling should only be performed by personnel trained and familiar with handling of potent active pharmaceutical ingredients. It is a moderate to severe irritant to the skin and eyes. Personal protective equipment such as NIOSH/MSHA-approved respirator and chemical-resistant rubber gloves are recommended.

Future Directions

Ropinirole is indicated for the treatment of Parkinson’s disease and restless legs syndrome. It is available as immediate-release (IR) and extended-release (ER) formulations. Both formulations are effective to Parkinson’s disease patients in the early and advanced stage. The dose and timing of Ropinirole in treating Parkinson’s disease is different from the dose and timing in treating RLS. Follow the directions on your prescription label.

Preparation Methods

Synthetic Routes and Reaction Conditions

The synthesis of Ropinirole D3 Hydrochloride involves the incorporation of deuterium atoms into the Ropinirole molecule This can be achieved through various methods, including the use of deuterated reagents or solvents during the synthesis processThe final step involves the formation of the hydrochloride salt .

Industrial Production Methods

Industrial production of this compound follows similar steps to the laboratory synthesis but on a larger scale. The process involves the use of high-purity deuterated reagents and solvents to ensure the incorporation of deuterium atoms. The reaction conditions are optimized to maximize yield and purity, and the final product is subjected to rigorous quality control measures to ensure its suitability for pharmaceutical use .

Chemical Reactions Analysis

Types of Reactions

Ropinirole D3 Hydrochloride undergoes various chemical reactions, including:

Oxidation: The compound can be oxidized to form various metabolites.

Reduction: Reduction reactions can occur, particularly in the presence of reducing agents.

Substitution: The compound can undergo substitution reactions, particularly at the dipropylaminoethyl side chain.

Common Reagents and Conditions

Oxidation: Common oxidizing agents include hydrogen peroxide and potassium permanganate.

Reduction: Reducing agents such as sodium borohydride and lithium aluminum hydride are commonly used.

Substitution: Substitution reactions often involve the use of halogenating agents or nucleophiles.

Major Products Formed

The major products formed from these reactions include various metabolites and derivatives of this compound, which can have different pharmacological properties .

Comparison with Similar Compounds

Similar Compounds

Pramipexole Dihydrochloride: Another dopamine agonist used in the treatment of Parkinson’s disease and Restless Legs Syndrome.

Rotigotine: A dopamine agonist available as a transdermal patch for the treatment of Parkinson’s disease.

Apomorphine: A dopamine agonist used for the treatment of advanced Parkinson’s disease.

Uniqueness

Ropinirole D3 Hydrochloride is unique due to the incorporation of deuterium atoms, which can enhance its pharmacokinetic properties. This can lead to improved efficacy, reduced side effects, and potentially longer duration of action compared to non-deuterated dopamine agonists .

Properties

IUPAC Name	4-[2-[propyl(3,3,3-trideuteriopropyl)amino]ethyl]-1,3-dihydroindol-2-one;hydrochloride	Source
Details	Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

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/i1D3;	Source
Details	Computed by InChI 1.0.6 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	XDXHAEQXIBQUEZ-NIIDSAIPSA-N	Source
Details	Computed by InChI 1.0.6 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CCCN(CCC)CCC1=C2CC(=O)NC2=CC=C1.Cl	Source
Details	Computed by OEChem 2.3.0 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Isomeric SMILES	[2H]C([2H])([2H])CCN(CCC)CCC1=C2CC(=O)NC2=CC=C1.Cl	Source
Details	Computed by OEChem 2.3.0 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C16H25ClN2O	Source
Details	Computed by PubChem 2.1 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Weight	299.85 g/mol	Source
Details	Computed by PubChem 2.1 (PubChem release 2021.05.07)
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Synthesis routes and methods I

Procedure details

A mixture of 5.83 g (16.9 mmoles) of 2-nitro-6-(2-di-n-propylaminoethyl)-phenyl acetic acid hydrochloride and 0.6 g of 5% palladium-on-carbon in 250 cc of ethanol was hydrogenated at moderate pressure over 5.5 hours. The catalyst was filtered, washed with ethanol, and the filtrate evaporated to dryness in vacuo. The white residue was crystallized from 550 cc of hot acetonitrile to give 3.89 g of 4-(2-di-n-propylaminoethyl)-2(3H)-indolone hydrochloride, mp 240°-2°.

Name

2-nitro-6-(2-di-n-propylaminoethyl)-phenyl acetic acid hydrochloride

Quantity

5.83 g

Type

reactant

Reaction Step One

Name

ethanol

Quantity

250 mL

Type

solvent

Reaction Step One

Name

palladium-on-carbon

Quantity

0.6 g

Type

catalyst

Reaction Step One

Name

4-(2-di-n-propylaminoethyl)-2(3H)-indolone hydrochloride

Details

Synthesis routes and methods II

Procedure details

2-Nitro-6-[2-(N,N-Di-n-propyl amino)ethyl]phenyl acetic acid hydrochloride (100 g) is dissolved methanol (2000 ml) and then hydrogenated in presence of 10% Palladium on charcoal. The reaction mixture is filtered to obtain clear solution. Methanol is distilled out under vacuum at 50° C. Isopropanol (100 ml) is added to the residue and it is cooled, filtered and washed with isopropanol to obtain light yellow crystalline Ropinirole hydrochloride. The product is dried at 60-70° C. under vacuum. Yield 65-75 g.

Name

2-Nitro-6-[2-(N,N-Di-n-propyl amino)ethyl]phenyl acetic acid hydrochloride

Quantity

100 g

Type

reactant

Reaction Step One

Name

methanol

Quantity

2000 mL

Type

solvent

Reaction Step One

Name

Palladium on charcoal

Quantity

0 (± 1) mol

Type

catalyst

Reaction Step Two

Name

Ropinirole hydrochloride

Details

Synthesis routes and methods III

Procedure details

The process as shown above comprises conversion of 2-methyl-3-nitro phenyl acetic acid (II) with thionyl chloride to 2-Methyl-3-nitro-phenylacetyl chloride (III), which upon reaction with Di-n-propyl amine (DPA) gives 2-Methyl-3-nitro phenyl-N,N-di-n-propyl acetamide (IV) in syrup form. This intermediate (IV) is further reduced with Borane/THF and subsequent treatment with HCl/NaOH to give 2-Methyl-3-nitro phenyl ethyl-N,N-di-n-propyl amine (V). Further, compound (V) is treated with Na metal, Ethanol and diethyl oxalate to obtain Ethyl 6-(2-di-n-propylaminoethyl)-2-nitrophenyl pyruvate (VI), which is further treated with hydrogen peroxide , NaOH and HCl and converted to 6-(2-Di-n-propylaminoethyl)-2-nitro phenyl acetic acid hydrochloride (VII). This intermediate is reduced with palladium/carbon to give Ropinirole hydrochloride (Ia).

Name

hydrogen peroxide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

NaOH

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

HCl

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

6-(2-Di-n-propylaminoethyl)-2-nitro phenyl acetic acid hydrochloride

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

palladium/carbon

Quantity

0 (± 1) mol

Type

catalyst

Reaction Step Three

Name

Ropinirole hydrochloride

Details

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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.

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