Pramiracetam
Descripción general
Descripción
Pramiracetam es un agente nootrópico que pertenece a la familia de fármacos racetam. Es un derivado sintético del piracetam, el primer nootrópico creado en laboratorio, pero es significativamente más potente. This compound se comercializa bajo varios nombres comerciales, incluyendo Pramistar, Neupramir y Remen. Se utiliza principalmente para mejorar la memoria y las funciones cognitivas, particularmente en individuos con demencias neurodegenerativas y vasculares .
Aplicaciones Científicas De Investigación
Cognitive Disorders
Pramiracetam has been studied for its effects on various cognitive disorders:
- Alzheimer's Disease : Early clinical trials indicated mixed results when tested on Alzheimer's patients; however, it was later repurposed for use in other cognitive impairments associated with neurodegenerative diseases .
- Traumatic Brain Injury (TBI) : Research has shown that this compound can improve cognitive deficits following TBI. A study indicated significant improvements in memory performance among subjects with head injuries .
- Post-Concussive Syndrome : It has been suggested that this compound may alleviate symptoms associated with post-concussive syndrome by enhancing cognitive recovery .
Vascular Dementia
This compound is marketed as "Pramistar" for treating concentration and memory disturbances due to vascular dementia. Clinical studies have demonstrated its efficacy in improving cognitive function in elderly patients suffering from these conditions .
Research Findings
Recent studies have provided insights into the efficacy and safety of this compound:
Safety and Dosage
This compound is generally considered safe when used at recommended dosages (typically between 200 to 600 mg/kg in animal studies) without significant adverse effects reported. However, long-term effects and safety in humans require further investigation to establish comprehensive safety profiles .
Mecanismo De Acción
El pramiracetam ejerce sus efectos mejorando la captación de colina de alta afinidad, que es un precursor de la acetilcolina. La acetilcolina es un neurotransmisor implicado en la memoria y el aprendizaje. El this compound también aumenta la actividad de la aldosterona en el cerebro, lo que mejora el tono simpático y media la respuesta de lucha o huida .
Análisis Bioquímico
Biochemical Properties
Pramiracetam is believed to indirectly affect the release of neurotransmitters, brain chemicals that transmit signals from one nerve cell to another .
Cellular Effects
This compound has been shown to improve memory in healthy elderly adults with memory loss and enhance overall cognition in young adults with memory problems . It is also suggested to optimize overall brain function and increase focus and productivity .
Molecular Mechanism
The molecular mechanism of action of this compound is not well known . It might enhance acetylcholine synthesis
Temporal Effects in Laboratory Settings
It is effective when taken acutely (1-2 hours) before cognitive testing .
Dosage Effects in Animal Models
In animal studies, this compound has shown benefits to long-term memory formation in both young and old rats . The effects of varying dosages of this compound in animal models have not been extensively studied .
Metabolic Pathways
It is suggested that this compound might enhance acetylcholine synthesis
Transport and Distribution
Information on how this compound is transported and distributed within cells and tissues is currently limited .
Subcellular Localization
The subcellular localization of this compound and its effects on activity or function are not well known
Métodos De Preparación
Rutas Sintéticas y Condiciones de Reacción
El pramiracetam se sintetiza a partir del piracetam mediante la sustitución del grupo amida por un grupo dipropan-2-ylaminoetil. La síntesis implica una reacción de condensación, disolución y filtración, redisolución y extracción, reflujo, congelación y filtración por succión . El proceso es relativamente sencillo, lo que lo hace adecuado para la producción a gran escala.
Métodos de Producción Industrial
La producción industrial del this compound implica la reacción del éster etílico de pirrolidona con N,N-diisopropiletilendiamina. Esta reacción se lleva a cabo en un sistema bifásico de tolueno-agua utilizando carbonato de sodio como catalizador. El intermedio resultante se hace reaccionar entonces con la sal sódica de pirrolidona en una solución de tolueno, seguido de calentamiento y eliminación del metanol para obtener this compound .
Análisis De Reacciones Químicas
Tipos de Reacciones
El pramiracetam se somete a diversas reacciones químicas, entre ellas:
Oxidación: El this compound se puede oxidar para formar los óxidos correspondientes.
Reducción: Las reacciones de reducción pueden convertir el this compound en sus formas reducidas.
Sustitución: El this compound puede sufrir reacciones de sustitución en las que los grupos funcionales son sustituidos por otros grupos.
Reactivos y Condiciones Comunes
Oxidación: Los agentes oxidantes comunes incluyen permanganato de potasio y peróxido de hidrógeno.
Reducción: Se utilizan agentes reductores como el hidruro de litio y aluminio y el borohidruro de sodio.
Sustitución: Las reacciones de sustitución suelen implicar reactivos como halógenos y agentes alquilantes.
Productos Principales
Los productos principales formados a partir de estas reacciones incluyen diversos derivados de this compound, como sus óxidos, formas reducidas y compuestos sustituidos.
Comparación Con Compuestos Similares
El pramiracetam forma parte de la familia racetam, que incluye varios compuestos similares:
Piracetam: El primer nootrópico, utilizado para la mejora cognitiva pero menos potente que el this compound.
Aniracetam: Conocido por sus propiedades ansiolíticas.
Oxiracetam: Utilizado por sus efectos estimulantes en el sistema nervioso central.
Fenilpiracetam: Más potente y utilizado para un rango más amplio de indicaciones.
Coluracetam: Conocido por sus efectos en la captación de colina.
Nefiracetam: Investigado por su potencial en el tratamiento de deterioros cognitivos .
El this compound es único debido a su alta potencia y mecanismo de acción específico, lo que lo convierte en un compuesto valioso en el campo de la mejora cognitiva.
Actividad Biológica
Pramiracetam, a derivative of piracetam, is classified as a nootropic compound known for its potential cognitive-enhancing effects. This article delves into its biological activity, focusing on neurochemical properties, pharmacological effects, and clinical findings.
This compound exhibits unique neurochemical interactions that differentiate it from other racetams. Research has shown that this compound does not significantly alter the levels of various neurotransmitters such as norepinephrine, dopamine, and serotonin when administered at doses of 100 mg/kg. However, it does enhance high-affinity choline uptake (HACU) in hippocampal synaptosomes, indicating a potential mechanism for its cognitive-enhancing effects.
| Dose (mg/kg) | Effect on HACU | Comments |
|---|---|---|
| 8.8 | No effect | Control group |
| 44 | +30% | Significant increase |
| 88 | +37% | Significant increase |
| 100 | No effect | Similar to control |
| 176 | No effect | Similar to control |
This data suggests that this compound may enhance cholinergic activity selectively without affecting other neurotransmitter systems significantly .
Pharmacological Effects
This compound has been studied for its effects on learning and memory. In animal models, it has demonstrated improvements in memory retention and cognitive function. For instance, in a study assessing recognition memory in rats, this compound improved performance in a one-trial test paradigm .
Additionally, this compound has shown efficacy in counteracting cognitive deficits induced by scopolamine, a muscarinic antagonist. This indicates its potential as a therapeutic agent for conditions characterized by cognitive impairment.
Clinical Studies and Case Reports
-
Attention-Deficit Hyperactivity Disorder (ADHD) Study : A double-blind placebo-controlled trial investigated the effects of this compound as an adjunct therapy in children with ADHD. The results indicated significant improvements in behavioral scores when combined with methylphenidate compared to placebo .
Table 1: ADHD Study Results
Measurement Tool MPH + Piracetam MPH + Placebo CPRS-R Score Change Significant Decrease Not Significant CGI-I Improvement Rate 83.3% 38.8% - Dissociative Symptoms Case Report : A case study reported dissociative symptoms associated with the use of Piracetam (which shares structural similarities with this compound). The symptoms resolved after discontinuation of the drug, suggesting that while these compounds are generally well-tolerated, they may have adverse psychological effects in certain individuals .
Summary of Findings
This compound's biological activity is characterized by:
- Enhanced Cholinergic Activity : Increased HACU without significant changes to other neurotransmitter levels.
- Cognitive Enhancement : Positive effects on memory and learning in both animal models and clinical settings.
- Potential Side Effects : Although generally well-tolerated, there are reports of psychological side effects that warrant caution.
Propiedades
IUPAC Name |
N-[2-[di(propan-2-yl)amino]ethyl]-2-(2-oxopyrrolidin-1-yl)acetamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C14H27N3O2/c1-11(2)17(12(3)4)9-7-15-13(18)10-16-8-5-6-14(16)19/h11-12H,5-10H2,1-4H3,(H,15,18) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
ZULJGOSFKWFVRX-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(C)N(CCNC(=O)CN1CCCC1=O)C(C)C |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C14H27N3O2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Related CAS |
72869-16-0 (sulfate) |
Source
|
| Record name | Pramiracetam [INN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0068497621 | |
| 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. | |
DSSTOX Substance ID |
DTXSID60218604 |
Source
|
| Record name | Pramiracetam | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID60218604 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
269.38 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
68497-62-1 |
Source
|
| Record name | Pramiracetam | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=68497-62-1 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Pramiracetam [INN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0068497621 | |
| 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 | Pramiracetam | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB13247 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Pramiracetam | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID60218604 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | 68497-62-1 | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/information-on-chemicals | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | PRAMIRACETAM | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/4449F8I3LE | |
| 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. | |
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Retrosynthesis Analysis
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