(S)-3-Aminodihydrothiophen-2(3H)-one hydrochloride - 31828-68-9

(S)-3-Aminodihydrothiophen-2(3H)-one hydrochloride

Catalog Number: EVT-341014
CAS Number: 31828-68-9
Molecular Formula: C4H8ClNOS
Molecular Weight: 153.63 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
(S)-3-Aminodihydrothiophen-2(3H)-one hydrochloride, also known as levetiracetam, is a medication used to treat epilepsy. It was first approved by the US Food and Drug Administration (FDA) in 1999 and has since become a widely used antiepileptic drug. Levetiracetam is a member of the racetam family of drugs and is structurally similar to piracetam, another nootropic drug.
Applications in Various Fields
Levetiracetam has a variety of applications in medical research, including its role in drug development, clinical trials, and findings. The drug has been shown to be effective in the treatment of epilepsy, with fewer side effects than other antiepileptic drugs. It has also been shown to be effective in the treatment of migraine and neuropathic pain.
In environmental research, (S)-3-Aminodihydrothiophen-2(3H)-one hydrochloridem has been shown to have minimal effects on ecosystems and is not considered a significant pollutant. The drug has been used in pollution management to monitor the presence of pharmaceuticals in water sources.
In industrial research, (S)-3-Aminodihydrothiophen-2(3H)-one hydrochloridem has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations are important in the use of the drug in industrial settings.

Properties

CAS Number

31828-68-9

Product Name

(S)-3-Aminodihydrothiophen-2(3H)-one hydrochloride

IUPAC Name

(3S)-3-aminothiolan-2-one;hydrochloride

Molecular Formula

C4H8ClNOS

Molecular Weight

153.63 g/mol

InChI

InChI=1S/C4H7NOS.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1

InChI Key

ZSEGSUBKDDEALH-DFWYDOINSA-N

SMILES

C1CSC(=O)C1N.Cl

Synonyms

(3S)-3-Aminodihydro-2(3H)-thiophenone Hydrochloride; (S)-3-Aminodihydro-2(3H)-thiophenone Hydrochloride; L-3-Aminodihydro-2(3H)-thiophenone Hydrochloride

Canonical SMILES

C1CSC(=O)C1N.Cl

Isomeric SMILES

C1CSC(=O)[C@H]1N.Cl
Method of Synthesis or Extraction
Levetiracetam is synthesized through a multi-step process starting from 2-acetylthiophene. The first step involves the reaction of 2-acetylthiophene with ammonia to form 2-aminothiophene. This is followed by a cyclization reaction with chloroacetyl chloride to form (S)-3-chloro-2-oxo-1-pyrrolidineacetamide. The final step involves the reaction of (S)-3-chloro-2-oxo-1-pyrrolidineacetamide with ethylamine to form (S)-3-Aminodihydrothiophen-2(3H)-one hydrochloride.
The efficiency and yield of the synthesis process depend on the reaction conditions and the purity of the starting materials. The overall yield of the synthesis process is around 50%. The synthesis process is relatively safe and environmentally friendly, with no significant environmental impact.
Chemical Structure and Biological Activity
Levetiracetam is a white crystalline powder with a molecular weight of 170.6 g/mol. Its chemical formula is C8H14N2O2S.HCl. The drug acts by binding to the synaptic vesicle protein 2A (SV2A) in the brain, which is involved in the release of neurotransmitters. This binding inhibits the release of neurotransmitters, thereby reducing the likelihood of seizures.
Levetiracetam has a high bioavailability and is rapidly absorbed after oral administration. The drug has a half-life of around 6-8 hours and is primarily excreted unchanged in the urine. The drug is well-tolerated, with few side effects.
Biological Effects
Levetiracetam has been shown to have a variety of effects on cell function and signal transduction. The drug has been shown to modulate the release of neurotransmitters, including glutamate and GABA. It has also been shown to affect the activity of ion channels, including voltage-gated calcium channels and potassium channels.
Levetiracetam has been shown to have potential therapeutic effects in a variety of neurological disorders, including epilepsy, migraine, and neuropathic pain. The drug has also been shown to have potential toxic effects, including cognitive impairment and behavioral changes.
Future Perspectives and Challenges
Current limitations in the use and study of (S)-3-Aminodihydrothiophen-2(3H)-one hydrochloridem include its potential toxic effects and the need for further research to fully understand its mechanism of action. Possible solutions and improvements include the development of new formulations and the identification of new targets for the drug.
Future trends and prospects in the application of (S)-3-Aminodihydrothiophen-2(3H)-one hydrochloridem in scientific research include the development of new drugs based on its structure and the identification of new therapeutic targets. The drug has the potential to be used in the treatment of a variety of neurological disorders, including Alzheimer's disease and Parkinson's disease.

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