(R)-Rivastigmine

Katalognummer: B1354846

CAS-Nummer: 415973-05-6

Molekulargewicht: 250.34 g/mol

InChI-Schlüssel: XSVMFMHYUFZWBK-LLVKDONJSA-N

Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.

Auf Lager

Klicken Sie auf QUICK INQUIRY, um ein Angebot von unserem Expertenteam zu erhalten.
Mit qualitativ hochwertigen Produkten zu einem WETTBEWERBSFÄHIGEN Preis können Sie sich mehr auf Ihre Forschung konzentrieren.

Übersicht

1. Beschreibung

6. Eigenschaften

2. Vorbereitungsmethoden

7. Synthesis routes and methods

3. Wissenschaftliche Forschungsanwendungen

8. Retrosynthesis analysis

4. Wirkmechanismus

9. Q & A

5. Vergleich mit ähnlichen Verbindungen

10. Haftungsausschluss

Beschreibung

®-Rivastigmine is a chiral carbamate derivative used as a medication for the treatment of mild to moderate dementia associated with Alzheimer’s disease and Parkinson’s disease. It functions as a cholinesterase inhibitor, enhancing cholinergic function by increasing the concentration of acetylcholine through reversible inhibition of its hydrolysis by cholinesterase.

Vorbereitungsmethoden

Synthetic Routes and Reaction Conditions: The synthesis of ®-Rivastigmine typically involves the following steps:

Formation of the Chiral Intermediate: The chiral intermediate is synthesized through the reaction of ®-3-(1-dimethylaminoethyl)phenol with 3-bromopropylamine hydrobromide.

Carbamate Formation: The intermediate is then reacted with methyl isocyanate to form ®-Rivastigmine.

Industrial Production Methods: Industrial production of ®-Rivastigmine involves large-scale synthesis using optimized reaction conditions to ensure high yield and purity. The process includes:

Batch Processing: Utilizing batch reactors for the controlled addition of reagents.

Purification: Employing techniques such as crystallization and chromatography to purify the final product.

Types of Reactions:

Oxidation: ®-Rivastigmine can undergo oxidation reactions, typically in the presence of strong oxidizing agents.

Reduction: Reduction reactions can occur under specific conditions, although they are less common.

Substitution: The compound can participate in nucleophilic substitution reactions, particularly at the carbamate group.

Common Reagents and Conditions:

Oxidation: Reagents such as hydrogen peroxide or potassium permanganate.

Reduction: Reagents like lithium aluminum hydride.

Substitution: Nucleophiles such as amines or thiols.

Major Products:

Oxidation: Oxidized derivatives of ®-Rivastigmine.

Reduction: Reduced forms of the compound.

Substitution: Substituted carbamate derivatives.

Wissenschaftliche Forschungsanwendungen

®-Rivastigmine has a wide range of applications in scientific research:

Chemistry: Used as a model compound to study cholinesterase inhibition and related mechanisms.

Biology: Investigated for its effects on neurotransmitter levels and neuronal function.

Medicine: Extensively studied for its therapeutic potential in neurodegenerative diseases.

Industry: Utilized in the development of new cholinesterase inhibitors and related pharmaceuticals.

Wirkmechanismus

®-Rivastigmine exerts its effects by inhibiting acetylcholinesterase and butyrylcholinesterase, enzymes responsible for the breakdown of acetylcholine. By inhibiting these enzymes, ®-Rivastigmine increases the concentration of acetylcholine in the synaptic cleft, enhancing cholinergic transmission. This mechanism is particularly beneficial in conditions like Alzheimer’s disease, where cholinergic deficits are prominent.

Vergleich Mit ähnlichen Verbindungen

Donepezil: Another cholinesterase inhibitor used in Alzheimer’s disease.

Galantamine: A natural alkaloid with cholinesterase inhibitory properties.

Tacrine: An older cholinesterase inhibitor with a similar mechanism of action.

Comparison:

Uniqueness: ®-Rivastigmine is unique in its dual inhibition of both acetylcholinesterase and butyrylcholinesterase, whereas Donepezil primarily inhibits acetylcholinesterase.

Efficacy: Studies suggest that ®-Rivastigmine may offer benefits in patients who do not respond to other cholinesterase inhibitors.

Side Effects: The side effect profile of ®-Rivastigmine is comparable to other cholinesterase inhibitors, with gastrointestinal symptoms being the most common.

Eigenschaften

IUPAC Name	[3-[(1R)-1-(dimethylamino)ethyl]phenyl] N-ethyl-N-methylcarbamate	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C14H22N2O2/c1-6-16(5)14(17)18-13-9-7-8-12(10-13)11(2)15(3)4/h7-11H,6H2,1-5H3/t11-/m1/s1	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	XSVMFMHYUFZWBK-LLVKDONJSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CCN(C)C(=O)OC1=CC=CC(=C1)C(C)N(C)C	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Isomeric SMILES	CCN(C)C(=O)OC1=CC=CC(=C1)[C@@H](C)N(C)C	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C14H22N2O2	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

DSSTOX Substance ID	DTXSID90194422	Source
Record name	Rivastigmine, (R)-
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID90194422
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	250.34 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

CAS No.	415973-05-6	Source
Record name	Rivastigmine, (R)-
Source	ChemIDplus
URL	https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0415973056
Description	ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system.

Record name	Rivastigmine, (R)-
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID90194422
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Record name	RIVASTIGMINE, (R)-
Source	FDA Global Substance Registration System (GSRS)
URL	https://gsrs.ncats.nih.gov/ginas/app/beta/substances/Z25UDQ15MV
Description	The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions.
Explanation	Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.

Synthesis routes and methods

Procedure details

The process of the present invention for example involves reacting 3-[1-(dimethylamino)ethyl]phenol with N-ethyl-N-methyl-4-nitrophenyl carbamate in the presence of potassium carbonate and dimethyl sulfoxide at a temperature ranging from about 80° C. to about 120° C. for about 30 to 40 hours, to form racemate of ethylmethylcarbamic acid 3-[1-(dimethylamino)ethyl]phenyl ester in the free base form. This racemate is then resolved to obtain the (S)-ethylmethylcarbamic acid 3-[1-(dimethylamino)ethyl]phenyl ester. The preferred method of resolution of the (S)-isomer from the racemate involves dissolving a mixture of the free base of the racemate and (+)-di-O, O′-p-toluoyl tartaric acid monohydrate in a 2:1 mixture of methanol:water by heating, collecting the precipitate on cooling by filtration, crystallizing the precipitate from a 2:1 mixture of ethanol:water, and obtaining the substantially pure (S)-isomer by partitioning it between 1N sodium hydroxide and a suitable organic solvent. The base may further be converted to its pharmaceutically acceptable acid addition salts, such as L(+)-tartrate salt.

Name

3-[1-(dimethylamino)ethyl]phenol

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

[Compound]

Name

N-ethyl-N-methyl-4-nitrophenyl carbamate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

potassium carbonate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

dimethyl sulfoxide

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Four

Name

ethylmethylcarbamic acid 3-[1-(dimethylamino)ethyl]phenyl ester

Details

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.

Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.

Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

(R)-Rivastigmine

Reactant of Route 2

(R)-Rivastigmine

Reactant of Route 3

(R)-Rivastigmine

Reactant of Route 4

(R)-Rivastigmine

Reactant of Route 5

(R)-Rivastigmine

Reactant of Route 6

(R)-Rivastigmine

Customer

Q & A

Q1: What is unique about the synthesis method for (R)-N-ethyl-N-methyl carbamic acid-3-(1-hydroxyethyl) phenyl ester described in the research?

A1: The research highlights a novel approach to synthesizing (R)-N-ethyl-N-methyl carbamic acid-3-(1-hydroxyethyl) phenyl ester, a crucial intermediate in the production of (R)-Rivastigmine []. This method boasts high stereoselectivity, utilizing a chiral catalyst to achieve an enantiomeric excess (ee) exceeding 98% for the desired (R)-enantiomer []. Remarkably, this impressive selectivity is achieved with a remarkably low catalyst loading, requiring just 1/100,000th to 1/1,000,000th of the reactant amount []. This efficient use of the catalyst, coupled with the method's ability to achieve complete reactant conversion, underscores its potential for large-scale production of this important pharmaceutical intermediate.

Haftungsausschluss und Informationen zu In-Vitro-Forschungsprodukten

Bitte beachten Sie, dass alle Artikel und Produktinformationen, die auf BenchChem präsentiert werden, ausschließlich zu Informationszwecken bestimmt sind. Die auf BenchChem zum Kauf angebotenen Produkte sind speziell für In-vitro-Studien konzipiert, die außerhalb lebender Organismen durchgeführt werden. In-vitro-Studien, abgeleitet von dem lateinischen Begriff "in Glas", beinhalten Experimente, die in kontrollierten Laborumgebungen unter Verwendung von Zellen oder Geweben durchgeführt werden. Es ist wichtig zu beachten, dass diese Produkte nicht als Arzneimittel oder Medikamente eingestuft sind und keine Zulassung der FDA für die Vorbeugung, Behandlung oder Heilung von medizinischen Zuständen, Beschwerden oder Krankheiten erhalten haben. Wir müssen betonen, dass jede Form der körperlichen Einführung dieser Produkte in Menschen oder Tiere gesetzlich strikt untersagt ist. Es ist unerlässlich, sich an diese Richtlinien zu halten, um die Einhaltung rechtlicher und ethischer Standards in Forschung und Experiment zu gewährleisten.

Schnellanfrage

Name *

E-Mail *

Telefon

Land

Produktname

Menge *

Nachricht