Piracetam
Overview
Description
Piracetam is a nootropic drug belonging to the racetams group, with the chemical name 2-oxo-1-pyrrolidine acetamide. It is a cyclic derivative of the neurotransmitter gamma-aminobutyric acid (GABA). This compound was first marketed by UCB Pharma in 1971 and is known for its cognitive-enhancing properties. It is used in various cognitive disorders, vertigo, cortical myoclonus, dyslexia, and sickle cell anemia .
Scientific Research Applications
Piracetam has a wide range of scientific research applications:
Chemistry: Used as a model compound for studying the properties of cyclic amides and their derivatives.
Biology: Investigated for its effects on cell membrane fluidity and neuroprotection.
Medicine: Used in the treatment of cognitive disorders, myoclonus, and sickle cell anemia. It has also been studied for its potential benefits in conditions like dementia, vertigo, and dyslexia.
Industry: Utilized in the development of nootropic supplements and cognitive enhancers .
Mechanism of Action
Target of Action
Piracetam is a cyclic derivative of the neurotransmitter γ-aminobutyric acid (GABA) and shares the same 2-oxo-pyrrolidone base structure with pyroglutamic acid . Its mechanism of action differs from that of endogenous gaba .
Mode of Action
This compound’s mode of action involves modulation of neurotransmitters, enhanced brain metabolism, improved blood flow, neuroprotection, and facilitation of neuronal communication . It also has effects on the vascular system by reducing erythrocyte adhesion to the vascular endothelium, hindering vasospasms, and facilitating microcirculation .
Biochemical Pathways
This compound has been found to inhibit the PI3K/Akt/mTOR pathway in OGD-stimulated SH-SY5Y cells . This pathway is involved in cell cycle regulation and is often dysregulated in diseases
Safety and Hazards
Piracetam is generally well-tolerated, but it may cause anemia, cough, CNS depression, drowsiness, headache, heart damage, lassitude (weakness, exhaustion), liver damage, narcosis, reproductive effects, teratogenic effects . It is advised to avoid contact with skin, eyes and clothing, ingestion and inhalation, and prolonged or repeated exposure .
Future Directions
While there is a growing interest in nootropic drugs like Piracetam for the treatment of CNS disorders, more research is needed to fully understand its long-term safety and potential risks . The efficacy of this compound in enhancing cognitive function in various populations, including healthy adults, individuals with cognitive decline, and patients with neurological disorders has been demonstrated in several studies .
Biochemical Analysis
Biochemical Properties
Piracetam interacts with various enzymes, proteins, and other biomolecules. It shares the same 2-oxo-pyrrolidone base structure with pyroglutamic acid and is a cyclic derivative of the neurotransmitter γ-aminobutyric acid (GABA) . Its mechanism of action differs from that of endogenous GABA . This compound has neuroprotective and anticonvulsant properties and is reported to improve neural plasticity .
Cellular Effects
This compound has significant effects on various types of cells and cellular processes. It enhances the growth of cells, inhibits oxidative stress, and improves mitochondrial function . It influences cell function by modulating neurotransmission in a range of transmitter systems, including cholinergic and glutamatergic systems .
Molecular Mechanism
This compound exerts its effects at the molecular level through various mechanisms. It influences neuronal and vascular functions by restoring cell membrane fluidity . This mechanism of action is thought to improve membrane stability, allowing the membrane and transmembrane proteins to maintain and recover the three-dimensional structure or folding for normal function .
Temporal Effects in Laboratory Settings
This compound shows changes in its effects over time in laboratory settings. It has been observed that this compound increases regional cerebral blood flow . This suggests that this compound might have long-term effects on cellular function observed in in vitro or in vivo studies .
Dosage Effects in Animal Models
The effects of this compound vary with different dosages in animal models. For instance, daily this compound treatment at doses of 0, 75, 150, and 300 mg/kg ip was initiated in 6-week-old male mice. The study found that low doses of this compound reduced search time in the visible-platform component, while all this compound doses prevented trial-related improvements in performance .
Metabolic Pathways
This compound is involved in various metabolic pathways. It has been shown to alter the physical properties of the plasma membrane by increasing its fluidity and protecting the cell against hypoxia . It also increases red cell deformability and normalizes the aggregation of hyperactive platelets .
Transport and Distribution
This compound is transported and distributed within cells and tissues. After oral ingestion, this compound is rapidly absorbed with a bioavailability of 100%. Its volume of distribution is 0.6 L/kg and plasma protein binding is 0% .
Subcellular Localization
It is known that this compound influences neuronal and vascular functions by restoring cell membrane fluidity . This suggests that this compound might have specific targeting signals or post-translational modifications that direct it to specific compartments or organelles.
Preparation Methods
Synthetic Routes and Reaction Conditions
Piracetam can be synthesized through several methods. One common method involves the reaction of 2-pyrrolidone with ethyl chloroacetate in the presence of a base, followed by hydrolysis to yield this compound. Another method involves the cyclization of gamma-aminobutyric acid (GABA) with acetic anhydride .
Industrial Production Methods
Industrial production of this compound typically involves large-scale synthesis using the aforementioned methods. The process is optimized for high yield and purity, ensuring that the final product meets pharmaceutical standards. The production process includes steps such as crystallization, filtration, and drying to obtain the pure compound .
Chemical Reactions Analysis
Types of Reactions
Piracetam undergoes various chemical reactions, including:
Oxidation: this compound can be oxidized to form 2-pyrrolidone-5-carboxylic acid.
Reduction: Reduction of this compound can yield 2-pyrrolidone.
Substitution: Substitution reactions can occur at the acetamide group, leading to the formation of various derivatives
Common Reagents and Conditions
Oxidation: Common oxidizing agents include potassium permanganate and hydrogen peroxide.
Reduction: Reducing agents such as lithium aluminum hydride can be used.
Substitution: Reagents like alkyl halides and acyl chlorides are commonly used for substitution reactions
Major Products Formed
Oxidation: 2-pyrrolidone-5-carboxylic acid
Reduction: 2-pyrrolidone
Substitution: Various acetamide derivatives
Comparison with Similar Compounds
Piracetam is often compared with other racetams, including:
Oxiracetam: Known for its stimulating effects and used for cognitive enhancement.
Aniracetam: Has anxiolytic properties and is used for anxiety and cognitive disorders.
Pramiracetam: More potent than this compound, used for cognitive deficits associated with traumatic brain injuries.
Phenylthis compound: More potent and used for a wider range of indications, including cognitive enhancement and physical performance .
This compound is unique in its well-documented safety profile and broad range of applications, making it a versatile compound in both research and clinical settings.
Properties
IUPAC Name |
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/C6H10N2O2/c7-5(9)4-8-3-1-2-6(8)10/h1-4H2,(H2,7,9) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
GMZVRMREEHBGGF-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1CC(=O)N(C1)CC(=O)N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C6H10N2O2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID5044491 |
Source
|
| Record name | 2-Oxo-1-Pyrrolidineacetamide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID5044491 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
142.16 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Boiling Point |
Decomposes |
Source
|
| Record name | Piracetam | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB09210 | |
| 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) | |
Mechanism of Action |
Piracetam interacts with the polar heads in the phospholipids membrane and the resulting mobile drug-lipid complexes are thought to reorganize the lipids and influence membrane function and fluidity. Such interaction has been reported in a study that investigated the effects of neuronal outgrowth induced by beta amyloid peptides; while amyloid peptides cause lipid disorganization within the cell membranes leading to neuronal death, piracetam demonstrated to decrease the destabilizing effects of amyloid peptide. The authors suggest that piracetam induces a positive curvature of the membrane by occupying the polar groups in the phospholipids to counteract the negative curvature induced by amyloid peptides , which in turn would decrease the likelihood of membrane fusion. This mechanism of action is thought to improve membrane stability, allowing the membrane and transmembrane proteins to maintain and recover the three-dimensional structure or folding for normal function such as membrane transport, chemical secretion, and receptor binding and stimulation. Through restored membrane fluidity, piracetam promotes restored neurotransmission such as glutamatergic and cholinergic systems, enhances neuroplasticity and mediates neuroprotective and anticonvulsant effects at the neuronal level. It is also demonstrated that piracetam also improves the fluidity of platelet membranes. At the vascular level, piracetam decreases adhesion of erythrocytes to cell wall and reduces vasospasm which in turn improves microcirculation including cerebral and renal blood flow., It was found that a drug of the nootropic nature piracetam possessing pronounced antihypoxic properties eliminates calcium chloride-induced disturbances of the cardiac rhythm and significantly raises the threshold of atrial fibrillation during electrical stimulation. The drug's antiarrhythmic effect is followed by a decrease of the rhythm rate and an increase of the contraction amplitude. The animals treated with piracetam in a dose when its antiarrhythmic effects (300 mg/kg) exhibited a decrease of the membrane potential of erythrocytes as compared with control. Similar effects occurred in the animals treated with lidocaine. It can be concluded that in certain types of arrhythmias the use of piracetam restores the normal rhythm of contractions that is perhaps connected with its positive influence on metabolic processes in the myocardium. |
Source
|
| Record name | Piracetam | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB09210 | |
| 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 | PIRACETAM | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7529 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
Crystals from isopropanol | |
CAS No. |
7491-74-9 |
Source
|
| Record name | Piracetam | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=7491-74-9 | |
| 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 | Piracetam [USAN:INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0007491749 | |
| 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 | Piracetam | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB09210 | |
| 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 | piracetam | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=758191 | |
| Description | The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. | |
| Explanation | Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. | |
| Record name | 2-Oxo-1-Pyrrolidineacetamide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID5044491 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Piracetam | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.028.466 | |
| 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. | |
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| Record name | PIRACETAM | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/ZH516LNZ10 | |
| 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. | |
| Record name | PIRACETAM | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7529 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Melting Point |
151.5 - 152.5 °C |
Source
|
| Record name | Piracetam | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB09210 | |
| 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 | PIRACETAM | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7529 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Retrosynthesis Analysis
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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
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