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Piracetam

PubChem CID
4843
Structure
Piracetam_small.png
Piracetam_3D_Structure.png
Piracetam__Crystal_Structure.png
Molecular Formula
Synonyms
  • piracetam
  • 7491-74-9
  • 2-(2-oxopyrrolidin-1-yl)acetamide
  • Nootropil
  • 2-Oxo-1-pyrrolidineacetamide
Molecular Weight
142.16 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
Piracetam is an organonitrogen compound and an organooxygen compound. It is functionally related to an alpha-amino acid.
Piracetam is a nootropic drug in the racetams group, with chemical name 2-oxo-1-pyrrolidine acetamide. It shares the same 2-oxo-pyrrolidone base structure with pyroglutamic acid and is a cyclic derivative of the neurotransmitter γ-aminobutyric acid (GABA). However its mechanism of action differ from that of endogenous GABA. Piracetam has neuroprotective and anticonvulsant properties and is reported to improve neural plasticity. Its efficacy is documented in cognitive disorders and dementia, vertigo, cortical myoclonus, dyslexia, and sickle cell anemia although the clinical application in these conditions is not yet established. Piracetam has effects on the vascular system by reducing erythrocyte adhesion to the vascular endothelium, hindering vasospasms and facilitating microcirculation. Originally marketed by UCB Pharma in 1971, piracetam was the first nootropic drug to modulate cognitive function without causing sedation or stimulation. It is not approved for any medical or dietary use by the FDA. In the UK, piracetam is prescribed mainly for myoclonus, but is used off-label for other conditions such as learning difficulties in children, memory loss or other cognitive defects in the elderly, and sickle-cell vaso-occlusive crises. Evidence to support its use for many conditions is unclear.
PIRACETAM is a small molecule drug with a maximum clinical trial phase of IV (across all indications) and is indicated for attention deficit hyperactivity disorder and has 7 investigational indications.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Piracetam.png

1.2 3D Conformer

1.3 Crystal Structures

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CCDC Number
Associated Article
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(2-oxopyrrolidin-1-yl)acetamide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C6H10N2O2/c7-5(9)4-8-3-1-2-6(8)10/h1-4H2,(H2,7,9)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

GMZVRMREEHBGGF-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1CC(=O)N(C1)CC(=O)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C6H10N2O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

7491-74-9

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 NCI Thesaurus Code

2.3.12 Nikkaji Number

2.3.13 NSC Number

2.3.14 Wikidata

2.3.15 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2-Pyrrolidone-N-Acetamide
  • Avigilen
  • Axonyl
  • Cerebroforte
  • Cerepar N
  • Ciclofalina
  • Cuxabrain
  • Dinagen
  • Gabacet
  • Geram
  • Memo Puren
  • Memo-Puren
  • Nootrop
  • Nootropil
  • Nootropyl
  • Normabraïn
  • Piracebral
  • Piracetam
  • Piracetam AbZ
  • Piracetam RPh
  • Piracetam-RPh
  • Piracetrop
  • Pirazetam
  • Pyracetam
  • Pyramem
  • Sinapsan
  • UCB 6215
  • UCB-6215
  • UCB6215

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
142.16 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-1.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
142.074227566 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
142.074227566 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
63.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
167
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Color / Form

Crystals from isopropanol
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1342

3.2.2 Boiling Point

Decomposes
MSDS

3.2.3 Melting Point

152
MSDS
151.5 - 152.5 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1342

3.2.4 LogP

log Kow = -1.54
Altomore C et al; Chem Res Toxicol 5: 366-75 (1995)

3.2.5 Stability / Shelf Life

Nootropil 800 and 1200 mg Tablets: Four (4) years. Nootropil Solution 33%: Five (5) years.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/

3.2.6 Collision Cross Section

120.35 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

129.73 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

134.42 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111

3.2.7 Kovats Retention Index

Standard non-polar
1640

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484
Pharmaceuticals -> unsed in Switzerland 2014-2016
S113 | SWISSPHARMA24 | 2024 Swiss Pharmaceutical List with Metabolites | DOI:10.5281/zenodo.10501043
3.3.1.1 Human Drugs
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 4
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NIST Number
292144
Library
Main library
Total Peaks
64
m/z Top Peak
98
m/z 2nd Highest
70
m/z 3rd Highest
84
Thumbnail
Thumbnail
2 of 4
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NIST Number
335319
Library
Replicate library
Total Peaks
40
m/z Top Peak
98
m/z 2nd Highest
70
m/z 3rd Highest
84
Thumbnail
Thumbnail

4.1.2 MS-MS

1 of 7
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

98.0601 100

70.0651 56.06

69.0335 25.96

68.0495 4.32

126.0549 1.16

Thumbnail
Thumbnail
2 of 7
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

98.0601 100

70.0651 28.58

69.0335 9.77

126.055 3.35

68.0495 1.77

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4.1.3 LC-MS

1 of 23
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Authors
Kevin S. Jewell; Björn Ehlig; Arne Wick
Instrument
TripleTOF 5600 SCIEX
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
40
Fragmentation Mode
CID
Column Name
Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent
Retention Time
2.615 min
Precursor m/z
143.0815
Precursor Adduct
[M+H]+
Top 5 Peaks

60.9906 999

98.0602 380

70.0683 274

69.0361 159

102.013 88

Thumbnail
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License
dl-de/by-2-0
2 of 23
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Authors
Kevin S. Jewell; Björn Ehlig; Arne Wick
Instrument
TripleTOF 5600 SCIEX
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
50
Fragmentation Mode
CID
Column Name
Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent
Retention Time
2.615 min
Precursor m/z
143.0815
Precursor Adduct
[M+H]+
Top 5 Peaks

60.9914 999

69.0365 138

70.0673 111

43.991 64

Thumbnail
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License
dl-de/by-2-0

4.2 IR Spectra

4.2.1 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Composynth Chemicals
Catalog Number
PIR0059
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Composynth Chemicals
Catalog Number
PIR0059
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Indicated in adult patients suffering from myoclonus of cortical origin, irrespective of aetiology, and should be used in combination with other anti-myoclonic therapies.

7.2 Clinical Trials

7.2.1 ClinicalTrials.gov

7.2.2 EU Clinical Trials Register

7.3 Therapeutic Uses

/Investigators/ report on a 30-year-old patient with advanced cerebellar degeneration due to sickle cell amemia 2. He presented with severe myoclonus, which was resistant to conventional therapy and dramatically improved after administration of 12-18 g/day piracetam. Piracetam may be considered in the treatment of refractory myoclonus in spinocerebellar degenerations.
De Rosa A et al; Mov Disord 21 (1): 116-8 (2006)
/Piracetam/ is indicated for patients suffering from myoclonus of cortical origin, irrespective of etiology, and should be used in combination with other anti-myoclonic therapies.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/

7.4 Drug Warnings

Piracetam is contraindicated in patients with severe renal impairment (renal creatinine clearance of less than 20 mL per minute), hepatic impairment and to those under 16 years of age.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
Piracetam is contraindicated in patients with cerebral hemorrhage and in those with hypersensitivity to piracetam, other pyrrolidone derivatives or any of the excipients.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
Due to the effect of piracetam on platelet aggregation, caution is recommended in patients with underlying disorders of hemostasis, major surgery or severe hemorrhage.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
Abrupt discontinuation of treatment should be avoided as this may induce myoclonic or generalised seizures in some myoclonic patients.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
For more Drug Warnings (Complete) data for PIRACETAM (9 total), please visit the HSDB record page.

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Piracetam is known to mediate various pharmacodynamic actions: **Neuronal effects**: Piracetam modulates the cholinergic, serotonergic, noradrenergic, and glutamatergic neurotransmission although the drug does not display high affinity to any of the associated receptors (Ki >10μM). Instead, piracetam increases the density of postsynaptic receptors and/or restore the function of these receptors through stabilizing the membrane fluidity. In the forebrain of aging mice, the density of NMDA receptors was increased by approximately 20% following 14 days of piracetam treatment. Based on the findings of various animal and human studies, the cognitive processses including learning, memory, attention and consciousness were enhanced from piracetam therapy without inducing sedation and psychostimulant effects. Piracetam mediate neuroprotective effects against hypoxia-induced damage, intoxication, and electroconvulsive therapy. In two studies involving alcohol-treated rats with evidences of withdrawal-related neuronal loss, piracetam was shown to reduce the extent of neuronal loss and increase the numbers of synapses in the hippocampus by up to 20% relative to alcohol-treated or alcohol-withdrawn rats. This suggests that piracetam is capable in promoting neuroplasticity when recoverable neural circuits are present. Although the mechanism of action is not fully understood, administration of piracetam prior to a convulsant stimulus reduces the seizure severity and enhances the anticonvulsant effectiveness of conventional antiepileptics such as carbamazepine and diazepam. **Vascular effects**: Piracetam is shown to increase the deformability of erythrocytes, reduce platelet aggregation in a dose-dependent manner, reduce the adhesion of erythrocytes to vascular endothelium and capillary vasospasm. In healthy volunteers, piracetam mediated a direct stimulant effect on prostacycline synthesis and reduced the plasma levels of fibrinogen and von Willebrand’s factors (VIII: C; VIII R: AG; VIII R: vW) by 30 to 40%. Potentiated microcirculation is thought to arise from a combination of effects on erythrocytes, blood vessels and blood coagulation.

8.2 MeSH Pharmacological Classification

Nootropic Agents
Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. (See all compounds classified as Nootropic Agents.)
Neuroprotective Agents
Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)

8.3 ATC Code

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

N - Nervous system

N06 - Psychoanaleptics

N06B - Psychostimulants, agents used for adhd and nootropics

N06BX - Other psychostimulants and nootropics

N06BX03 - Piracetam

8.4 Absorption, Distribution and Excretion

Absorption
Piracetam displays a linear and time-dependent pharmacokinetic properties with low intersubject variability over a large range of doses. Piracetam is rapidly and extensively absorbed following oral administration with the peak plasma concentration is reached within 1 hour after dosing in fasted subjects. Following a single oral dose of 3.2 g piracetam, the peak plasma concentration (Cmax) was 84 µg/mL. Intake of food may decrease the Cmax by 17% and increase the time to reach Cmax (Tmax) from 1 to 1.5 hours. Tmax in the cerebrospinal fluid is achieved approximately 5 hours post-administration. The absolute bioavailability of piracetam oral formulations is close to 100% and the steady state plasma concentrations are achieved within 3 days of dosing.
Route of Elimination
Piracetam is predominantly excreted via renal elimination, where about 80-100% of the total dose is recovered in the urine. Approximately 90% of the dose of piracetam is excreted in the urine as unchanged drug.
Volume of Distribution
Vd is approximately 0.6L/kg. Piracetam may cross the blood-brain barrier as it was measured in the cerebrospinal fluid following intravenous administration. Piracetam diffuses to all tissues except adipose tissues, crosses placental barrier and penetrates the membranes of isolated red blood cells.
Clearance
The apparent total body clearance is 80-90 mL/min.
Piracetam is rapidly and almost completely absorbed. Peak plasma levels are reached within 1.5 hours after administration. The extent of oral bioavailability, assessed from the Area Under Curve (AUC), is close to 100% for capsules, tablets and solution.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
Peak levels and AUC are proportional to the dose given. The volume of distribution of piracetam is 0.7 L/kg, and ... Clearance of the compound is dependent on the renal creatinine clearance and would be expected to diminish with renal insufficiency.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
Piracetam is excreted in human breast milk.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
Piracetam crosses the blood-brain and the placental barrier and diffuses across membranes used in renal dialysis.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
Piracetam is excreted almost completely in urine and the fraction of the dose excreted in urine is independent of the dose given.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/

8.5 Metabolism / Metabolites

As large proportion of total piracetam administered is excreted as unchanged drug, there is no known major metabolism of piracetam.
... No metabolite of piracetam has been found.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/

8.6 Biological Half-Life

The plasma half life of piracetam is approximately 5 hours following oral or intravenous administration. The half life in the cerebrospinal fluid was 8.5 hours.
... The plasma half-life is 5.0 hours, in young adult men.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/

8.7 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.
Samvelian V et al; Farmakol Toksikol 53 (6): 22-3 (1990)

9 Use and Manufacturing

9.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Cerebral stimulant drug
Ashford, R.D. Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd., 1994., p. 720
MEDICATION
THERAP CAT: Nootropic
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1342

Use (kg; approx.) in Germany (2009): >50000

Consumption (g per capita; approx.) in Germany (2009): 0.611

Excretion rate: 0.95

Calculated removal (%): 92.1

9.1.1 Use Classification

Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

9.2 Methods of Manufacturing

... Prepared by condensing 2-pyrrolidinone with ethyl chloroacetate in the presence of a metal hydride and then converting the ester into an amide with ammonia.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V30 436 (2003)
Prepn: H. Morren, NL 6509994; eidem, US 3459738 (1966, 1969 both to U.C.B)
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1290

9.3 Formulations / Preparations

Nootropil 800 and 1200 mg Tablets: Polyethylene glycol 6000, Colloidal anhydrous silica, Magnesium stearate, Methocel, Titanium dioxide (E171), Polyethylene glycol 400. Nootropil Solution 33%: Glycerol, Methyl parahydroxybenzoate, Propyl parahydroxybenzoate, Sodium acetate, Acetic acid, Purified water
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
Avigilen
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1290
Axonyl
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1290
Ciclofalina
National Library of Medicine, SIS; ChemIDplus Record for Piracetum (7491-74-9) Available from, as of July 23, 2007: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp
For more Formulations/Preparations (Complete) data for PIRACETAM (19 total), please visit the HSDB record page.

9.4 General Manufacturing Information

January 7, 1999. ... /Piracetam is not/ the subject of a current United States Pharmacopeia or National Formulary monograph nor /a/ component of the Food and Drug Administration approved drugs, may be used in /pharmacy/ compounding under section 503A(b)(1)(A)(i)(III) of the Federal Food, Drug, and Cosmetic Act.
FDA; List of bulk drug substances that may be used in pharmacy compounds.21CFE216. Available from, as of Jun 7, 2007: https://www.fda.gov/cder/fdama/pclist.txt
As of October 2, 1987 piracetam (Trade name: Nootropil) is listed on the FDA's Cumulative List of All Orphan Designated Products. Piracetam's orphan designation is for the treatment of myoclonus and its sponsor is UCB, Inc. 1950 Lake Park Drive Smyrna, GA 30080
FDA; Cumulative List of All Orphan Designated Products (July 2007). Available from, as of July 31, 2007: https://www.fda.gov/orphan/designat/alldes.rtf

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 92.1% (58 of 63) of all reports. Pictograms displayed are for 7.9% (5 of 63) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 58 of 63 companies (only 7.9% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 63 reports by companies from 6 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 58 of 63 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 5 notifications provided by 5 of 63 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Not Classified

10.2 Accidental Release Measures

10.2.1 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

10.3 Handling and Storage

10.3.1 Storage Conditions

Tablets: None. Solution: Do not store above 25 °C
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/

10.4 Other Safety Information

Chemical Assessment

IMAP assessments - 1-Pyrrolidineacetamide, 2-oxo-: Environment tier I assessment

IMAP assessments - 1-Pyrrolidineacetamide, 2-oxo-: Human health tier I assessment

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

11.1.2 Interactions

... Confusion, irritability and sleep disorders /have been/ reported with concomitant use /of/ thyroid extract (T3 + T4) /and piracetam/.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
At present although based on a small number of patients, no interaction has been found with the following anti-epileptic medications: clonazepam, carbamazepine, phenytoin, phenobarbitone and sodium valproate.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
In a single-blind study on patients with severe recurrent venous thrombosis, piracetam 9.6 g/d did not modify the doses of acenocoumarol necessary to reach INR (international normalized ratio) 2.5 to 3.5, but compared with the effects of acenocoumarol alone, the addition of piracetam 9.6 g/d significantly decreased platelet aggregation, beta-thromboglobulin release, levels of fibrinogen and von Willebrand's factors (VIII : C; VIII : vW : Ag; VIII : vW : RCo) and whole blood and plasma viscosity.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/

11.1.3 Antidote and Emergency Treatment

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160-1

11.1.4 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Acute toxicological studies in animals showed lethal doses were obtained in mice (18.2 g/kg and higher) but not in rats and dogs dosed respectively at 21 g/kg or 10 g/kg.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ The only change which might eventually be attributed to chronic treatment in male, but not in female, rats was an increase of the incidence over control animals of progressive glomerulonephrosis at the dose of 2.4 g/kg/day given for 112 weeks.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Repeated oral treatment for up to 1 year in dogs (10 g/kg) and 6 months in rats (2 g/kg) was very well tolerated: no target organ toxicity or signs of (irreversible) toxicity were clearly demonstrated.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Although piracetam crosses the placenta into the fetal circulation, no teratogenic effects were observed at dose levels up to 4.8 g/kg/day (mice, rats) and 2.7 g/kg/day (rabbits). Furthermore, the compound affects neither fertility nor the peri- or postnatal development of the pregnancy at doses up to 2.7 g/kg/day.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/
/GENOTOXICITY/ Piracetam was found to be devoid of any mutagenic or clastogenic activity and does not represent any genotoxic ... risk to man.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/

11.1.5 Non-Human Toxicity Values

LD50 Mouse oral 26 g/kg
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from, as of July 31, 2007: https://emc.medicines.org.uk/

11.1.6 Protein Binding

Piracetam is not reported to be bound to plasma proteins.

11.2 Ecological Information

11.2.1 Environmental Water Concentrations

While data specific to piracetam were not located(SRC, 2007), the literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2).
(1) Heberer T; Tox Lett 131: 5-17 (2002)
(2) Koplin DW et al; Environ Sci Toxicol 36: 1202-211 (2002)

11.2.2 Milk Concentrations

Piracetam is excreted in human breast milk.
Medicines.org.uk; Nootropil 800mg & 1200mg Tablets and Solution. (UCB Pharma Limited; August 2005) electronic Medicines Compendium. Datapharm Communications. Available from: https://emc.medicines.org.uk/ as of July 31, 2007

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Chemical Co-Occurrences in Literature

13.7 Chemical-Gene Co-Occurrences in Literature

13.8 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Protein Bound 3D Structures

15.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

15.2 Chemical-Target Interactions

15.3 Drug-Drug Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 KEGG: Drug

17.5 KEGG: ATC

17.6 KEGG: Target-based Classification of Drugs

17.7 KEGG: Drug Groups

17.8 WHO ATC Classification System

17.9 ChemIDplus

17.10 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

17.11 ChEMBL Target Tree

17.12 UN GHS Classification

17.13 EPA CPDat Classification

17.14 NORMAN Suspect List Exchange Classification

17.15 CCSBase Classification

17.16 EPA DSSTox Classification

17.17 EPA Substance Registry Services Tree

17.18 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
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  4. DrugBank
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  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
  8. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  9. Hazardous Substances Data Bank (HSDB)
  10. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  11. ChEBI
  12. Open Targets
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    https://platform-docs.opentargets.org/licence
  13. ChEMBL
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  14. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  15. Comparative Toxicogenomics Database (CTD)
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    http://ctdbase.org/about/legal.jsp
  16. IUPHAR/BPS Guide to PHARMACOLOGY
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    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  17. Therapeutic Target Database (TTD)
  18. Crystallography Open Database (COD)
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    https://creativecommons.org/publicdomain/zero/1.0/
  19. The Cambridge Structural Database
  20. EPA Chemical and Products Database (CPDat)
  21. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    PIRACETAM
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  22. EU Clinical Trials Register
  23. Human Metabolome Database (HMDB)
    LICENSE
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    http://www.hmdb.ca/citing
  24. NIST Mass Spectrometry Data Center
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    https://www.nist.gov/srd/public-law
  25. Japan Chemical Substance Dictionary (Nikkaji)
  26. KEGG
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    https://www.kegg.jp/kegg/legal.html
    Therapeutic category of drugs in Japan
    http://www.genome.jp/kegg-bin/get_htext?br08301.keg
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
  27. MassBank Europe
  28. MassBank of North America (MoNA)
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    https://mona.fiehnlab.ucdavis.edu/documentation/license
  29. Metabolomics Workbench
  30. NCI Thesaurus (NCIt)
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    https://www.cancer.gov/policies/copyright-reuse
  31. SpectraBase
  32. WHO Anatomical Therapeutic Chemical (ATC) Classification
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    https://www.whocc.no/copyright_disclaimer/
  33. Protein Data Bank in Europe (PDBe)
  34. RCSB Protein Data Bank (RCSB PDB)
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  35. Springer Nature
  36. Thieme Chemistry
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  37. Wikidata
  38. Wikipedia
  39. Wiley
  40. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  41. PubChem
  42. GHS Classification (UNECE)
  43. EPA Substance Registry Services
  44. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  45. PATENTSCOPE (WIPO)
  46. NCBI
CONTENTS