ContaminantDB: Piracetam

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:47:04 UTC

Update Date

2016-11-09 01:15:42 UTC

Accession Number

CHEM017964

Identification

Common Name

Piracetam

Class

Small Molecule

Description

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 [A31532]. 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 [A31532]. Originally marketed by UCB Pharma in 1971, piracetam was the first nootropic drug to modulate cognitive function without causing sedation or stimulation [A31532]. 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 [L1124]. Evidence to support its use for many conditions is unclear.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Myocalm	Kegg
AbZ brand OF piracetam	MeSH
Almirall brand OF piracetam	MeSH
Alpharma brand OF piracetam	MeSH
Cerepar N	MeSH
Cuxabrain	MeSH
Hormona brand OF piracetam	MeSH
Nootropil	MeSH
Normabraïn	MeSH
Pfizer brand OF piracetam	MeSH
Piracebral	MeSH
Piracetam abz	MeSH
Piracetrop	MeSH
Pirazetam	MeSH
2-Pyrrolidone-N-acetamide	MeSH
Gabacet	MeSH
memo-Puren	MeSH
Merckle brand OF piracetam	MeSH
Nootropyl	MeSH
Piracetam RPH	MeSH
Pyramem	MeSH
Riemser brand OF piracetam	MeSH
Avigilen	MeSH
Azupharma brand OF piracetam	MeSH
Cerebroforte	MeSH
Hexal brand OF piracetam	MeSH
Holsten brand OF piracetam	MeSH
Sanofi synthelabo brand OF piracetam	MeSH
TAD brand OF piracetam	MeSH
UCB brand OF piracetam	MeSH
Vedim brand OF piracetam	MeSH
Axonyl	MeSH
Ciclofalina	MeSH
Dinagen	MeSH
Geram	MeSH
memo Puren	MeSH
Nootrop	MeSH
Piracetam-RPH	MeSH
Pyracetam	MeSH
Rodleben brand OF piracetam	MeSH
Sinapsan	MeSH
2-(2-Oxopyrrolidin-1-yl)ethanimidate	Generator

Chemical Formula

C₆H₁₀N₂O₂

Average Molecular Mass

142.156 g/mol

Monoisotopic Mass

142.074 g/mol

CAS Registry Number

7491-74-9

IUPAC Name

2-(2-oxopyrrolidin-1-yl)ethanimidic acid

Traditional Name

piracetam

SMILES

OC(=N)CN1CCCC1=O

InChI Identifier

InChI=1S/C6H10N2O2/c7-5(9)4-8-3-1-2-6(8)10/h1-4H2,(H2,7,9)

InChI Key

GMZVRMREEHBGGF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidone
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Primary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.76 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-2	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	5.24	ChemAxon
pKa (Strongest Basic)	7.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.39 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	46 m³·mol⁻¹	ChemAxon
Polarizability	13.95 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9100000000-91608c882f3d933f448d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-002b-9400000000-651dc28016b653b55d23	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-002b-9400000000-9c47f9c6616fbfad2c93	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9100000000-079c7eb43e2dcfe07d5f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9000000000-94d697783ea2c537498f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9000000000-5dd797bddeacd8764c16	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-006t-9000000000-e270872ffd02b3d53ab2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-006t-9000000000-0e9ffa0c462ebcb24c98	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0002-9000000000-d11cc02b12a44a1b0d59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0002-9100000000-f4ffa04f1852ef6412cc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0002-9000000000-2059b9ff4235f06ea33e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-002b-9400000000-8f8228043062c25afc06	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0005-8900000000-155fdc4c7c8d2caf2b26	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9100000000-37719f73983f0ee54ead	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-fef9a3341f7dc53b526c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-94ddc126d9251413a02c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-6900000000-e744f388669024ef6d66	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-7c593ee3fff4a54ba40d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB09210

HMDB ID

HMDB0256585

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Piracetam

Chemspider ID

4677

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Piracetam (CHEM017964)

Structure for CHEM017964: Piracetam