Oxiracetam Chemical Properties

Melting point:

165-168 °C

Boiling point:

494.6±40.0 °C(Predicted)

Density 

1.416

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly, Heated), Methanol (Slightly, Heated)

form 

Solid

pka

13.76±0.20(Predicted)

color 

White to Off-White

Merck 

14,6942

InChI

InChI=1S/C6H10N2O3/c7-5(10)3-8-2-4(9)1-6(8)11/h4,9H,1-3H2,(H2,7,10)

InChIKey

IHLAQQPQKRMGSS-UHFFFAOYSA-N

SMILES

N1(CC(N)=O)CC(O)CC1=O

CAS DataBase Reference

62613-82-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UX9656638

HS Code 

2933.79.8500

MSDS

• Language:English Provider:4-Hydroxy-2-oxopyrrolidine-N-acetamide
• Language:English Provider:SigmaAldrich

Oxiracetam Usage And Synthesis

Indications and Usage

Oxiracetam is a more potent derivative of the nootropic drug piracetam. They were developed in 1974 by the Italian company ICF and went on sale in 1987. Oxiracetam is a Piracetam derivative and excites the central nervous system, promotes brain metabolism, significantly increases and promotes memory retention, and effectively treats senile memory and mental decline. It is used to treat brain dysfunction psychiatric syndrome and mental disorders. It can improve the memory and learning abilities of patients with senile dementia or memory disorders. It is suitable for treating neural dysfunction, memory disorder and intelligence disorders caused by brain damage. It can also be used as a recovery treatment for neurosis, brain trauma, encephalitis, and other brain diseases. Oxiracetam’s greatest advantage is that it is very soluble in water, making it suitable for injection. Research shows that Oxiracetam has higher pharmacological activity and significant curative effects compared to Piracetam.

Mechanisms of Action

Oxiracetam’s mechanisms of action are similar to those of Piracetam. It promotes the binding of phosphorylcholine and phosphoethanolamine, increases the ratio of ATP/ADP in the brain, and increases the binding of protein with nucleic acids in the brain, thus improving the memory and learning ability of patients with senile dementia and memory disorder.

Pharmacokinetics

After intake, most of the drug will not accumulate in the body and will be excreted through urine in its original form. It is well-absorbed and well-tolerated.

Clinical Research

Animal trials showed that in all types of behavioral experiments, Oxiracetam can improve memory retention and learning ability, reduce brain shocks’ damage on memory, and prevent the learning abilities of rats suffering from spontaneous hypertensive cerebrovascular injury from decreasing. It can also increase acetylcholine circulation in rats’ skin and hippocampus, thus increasing affinity for choline uptake.

Description

Oxiracetam is a structural analogue of piracetam. This compound has enhancing effects on vigilance and memory. In comparison with piracetam, oxiracetam exhibits greater improvement in memory (Itil et al., 1986) and has been used extensively for the treatment of dementia, including AD, VaD, MID (Baumel et al., 1989; Dysken et al., 1989), and mixed forms. Green et al. (1992) failed to demonstrate a difference from placebo in AD patients. In contrast, Maina et al. (1989) studied 289 patients with MID in a double-blind placebo-controlled trial and after 12 weeks of treatment found that oxiracetam reduced behavioural symptoms.

Chemical Properties

Whie Solid

Originator

ISF (Italy)

Uses

Oxiracetam is a 4-hydroxy analog of piracetam with psychostimulant activity, reportedly useful in relieving the symptoms of cerebral insufficiency in the elderly.

Definition

ChEBI: Oxiracetam is an organooxygen compound and an organonitrogen compound. It is functionally related to an alpha-amino acid.

brand name

Neuromet

Biochem/physiol Actions

Nootropic agent, improves learning and memory, and prevents impairment of cognitive functions. Its mechanism of action in not yet known, but it is suggested to modulate glutamatergic and cholinergic neurotransmission. Protein kinase C may be involved.

Purification Methods

This nootropic (Alzheimer) drug is purified by recrystallisation from MeOH or aqueous Me2CO and dried in vacuo. [NMR, IR: Pifferi & Pinza Farmaco Ed Sci 32 602 1977, Banfi et al. Farmaco Ed Sci 39 16 1984, Gouilaev & Senning Brain Research Rev 19 180 1994.]

Oxiracetam(62613-82-5)Related Product Information

• Piracetam
• Oxiracetam
• 4-hydroxypyrrolidin-2-one
• (S)-4-Hydroxy-2-pyrrolidinone
• oxiracetaM related substance ISF3886
• Omeprazole
• Mecobalamin
• Pramiracetam
• Aniracetam
• Nefiracetam
• ILOPERIDONE
• Paliperidone
• 2-(2-oxo-2,5-dihydro-1H-pyrrol-1-yl)acetaMide
• methyl 4-hydroxy-2-oxopyrrolidine-1-acetate
• 2-[(carbamoylmethyl)amino]acetamide
• 4-Hydroxy-2-oxo-1-pyrrolidineacetic acid
• (4S)-4-hydroxy-2-oxo-1-Pyrrolidineacetic acid Methyl ester
• ethyl 4-hydroxy-2-oxopyrrolidine-1-acetate