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Piracetam ( CASNO:7491-74-9 )

Identification and Related Records
Name:
Piracetam
CAS Registry number:
7491-74-9
Iupac name:
2-(2-oxopyrrolidin-1-yl)acetamide
Synonyms:
Myocalm
Neuracetam
Nootobril
Nootobryl
Nootron
Nootrop
Nootropil
Nootropyl
Normabrain
Norzetam
(2-Oxopyrrolidino)acetamide
2-(2-Oxopyrrolidin-1-yl)acetamide
2-Ketopyrrolidine-1-acetamide
2-Oxo-1-pyrrolidineacetamide
2-Oxo-1-pyrrolidinylacetamide
2-Pyrrolidinoneacetamide
2-Pyrrolidoneacetamide
Avigilen
Axonyl
Cerebroforte
Cl 781
Encetrop
Euvifor
Gabacet
Genogris
Geram
EINECS(EC#):
231-312-7
Molecular Formula:
C6H10N2O2
Molecular Weight:
142.16
Inchi:
InChI=1/C6H10N2O2/c7-5(9)4-8-3-1-2-6(8)10/h1-4H2,(H2,7,9)
InChIKey:
GMZVRMREEHBGGF-UHFFFAOYSA-N
Canonical SMILES:
C1CC(=O)N(C1)CC(=O)N
Chemical and Physical Properties
Density:
1.239 g/cm3
Melting Point:
151-152 °C
Boiling Point:
408.3 °C at 760 mmHg
Refractive Index:
1.523
Flash Point:
200.8 °C
Solubilities:
Very soluble
Color/Form:
Crystals from isopropanol
Stability:
Stable at normal temperatures and pressures.
Storage temp:
Keep tightly closed.
Computed Properties:
Molecular Weight:142.1558 [g/mol]
Molecular Formula:C6H10N2O2
XLogP3-AA:-1.3
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:2
Tautomer Count:6
Exact Mass:142.074228
MonoIsotopic Mass:142.074228
Topological Polar Surface Area:63.4
Heavy Atom Count:10
Formal Charge:0
Complexity:167
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:1
Feature 3D Ring Count:1
Effective Rotor Count:2.8
Conformer Sampling RMSD:0.6
CID Conformer Count:5
Safety and Handling
Hazard Codes:
Xi: Irritant;
Risk Statements:
R36/37/38
Safety Statements:
26-37/39
Safety:
Hazard Codes:?IrritantXi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 2
RTECS: UX9660500
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
Avigilen
Axonyl
Ciclofalina
Cerebroforte
Encetrop
Gabacet
Genogris
Geram
Nootrop
Nootropil
Nootropyl
Norzetam
Normabrain
Piracebral
Pirroxil
Pyramem
Piracetrop
Sinapsan
Specification:
?Piracetam , its cas register number is 7491-74-9. It also can be called 1-Acetamido-2-pyrrolidinone ; 2-Ketopyrrolidine-1-ylacetamide ; 2-Oxo-1-pyrrolidineacetamide ; 2-Oxo-pyrrolidin-1-ylacetamide ; 2-Oxo-pyrrolidine acetamide ; 1-Pyrrolidineacetamide, 2-oxo- .It is?very soluble?in water.
Octanol/Water Partition Coefficient:
log Kow = -1.54
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.
Use and Manufacturing
Use and Manufacturing:
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.
Prepn: H. Morren, NL 6509994; eidem, US 3459738 (1966, 1969 both to U.C.B)
Usage:
Medication.
Biomedical Effects and Toxicity
Biological Activity:
Nootropic that displays cognitive enhancing properties. Proposed to enhance neurotransmission via modulation of ion flux; potentiates Na + influx through AMPA receptors. Facilitates efficiency of cholinergic neurotransmission at muscarinic receptors.
Pharmacological Action:
- 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.
- 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. While no potent nootropic drugs have yet been accepted for general use, several are being actively investigated.
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)]
Biomedical Effects and Toxicity:
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.
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.
Piracetam is excreted in human breast milk.
Piracetam crosses the blood-brain and the placental barrier and diffuses across membranes used in renal dialysis.
Piracetam is excreted almost completely in urine and the fraction of the dose excreted in urine is independent of the dose given.
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