Oxiracetam, ≥99%

OXIRACETAM ≥99% 

Chemical Name:    &nbsp4-Hydroxy-2-oxopyrrolidine-N-acetamide
Synonyms:     Hydroxypiracetam, 4-Hydroxy-2-oxopyrrolidine-N-acetamide, 62613-82-5, Neuractiv, Neuromet, ISF 2522, 4-Hydroxypiracetam

CAS #:    62613-82-5

Oxiracetam is a more potent derivative of the nootropic drug piracetam, which exhibits nootropic and mild energizing effects.

Form:    White powder
Molecular Formula:    C6H10N2O3

Molecular Weight:    158.16 g/mol
Melting Point:    165 - 174 °C




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Chemical Information:

CAS Number:62613-82-5
Purity:≥99%
Molecular Weight:158.16 g/mol
Melting Point:165 - 174 °C
Molecular Formula:C6H10N2O3
Synonyms: Hydroxypiracetam, 4-Hydroxy-2-oxopyrrolidine-N-acetamide, 62613-82-5, Neuractiv, Neuromet, ISF 2522, 4-Hydroxypiracetam
PubChem CID:4626
SMILES:O=C(N)CN1C(=O)CC(O)C1

Technical Information:

Application:Oxiracetam is a more potent derivative of the nootropic drug piracetam.
Appearance:White or off-white powder
Physical State:Solid
Solubility:Soluble to 5 mM in Ethanol, Freely soluble in Water.
Storage:Store at room temperature or cooler, in a sealed airtight container, protected from heat, light and humidity.
Stability:Stable for at least two years when stored as above.

Background:

Oxiracetam (4-hydroxy-2-oxo-pyrrolidinoacetamide) is a Nootropic compound of the pyrrolidinone class, based on Piracetam and developed as a stronger derivative.[1] Oxiracetam is of interest to individuals and institutions involved in neuroscience studies and in research related to neuroprotection, especially from cognitive impairment.

Oxiracetam has an added 4-hydroxl group, when compared to Piracetam. Studies have shown that the hydroxyl group improves the availability and efficacy of this compound, when compared to Piracetam. As an example, clinical studies using Oxiracetam tend to administer doses of up to 25 mg/kg/day, while clinical studies using Piracetam administer doses up to 300mg/kg/day.[2]

Oxiracetam is a GABA analogue that improves neuronal cell metabolism,[3] increases the sensitivity and activity of AMPA receptors,[4] and improves glutamate release[5] with a greater efficacy than Piracetam. Clinical applications of Oxiracetam include beneficial effects on cognition – including spatial orientation, logical processing, concentration, focus, attenetion, and long-term potentiatation. Most clinical studies were performed on patients suffering from ADHD or mild to moderate dementia.[6]

Animal studies have shown that Oxiracetam has a potent and reliable ability to prevent memory loss at an injected dosage range of between 3-30mg/kg.[7] Furthermore, Oxiracetam has been suggested to assist with improving memory formation in otherwise healthy rats and mice, after a minimum five-day loading period.[8]

Modes of action:

Oxiracetam has been shown to increase long-term potentiation (LTP) in rat hippocampal slices at a concentration of only 1µM.[9] The increase in LTP and positive modulation of receptor activity has been suggested to be an outcome of both an increase in glutamate and D-aspartic acid from activated hippocampal cells.

Significant pharmacological effects have been found to occur at a concentration range of 0.01-5µM.[10]

Importantly, research has pointed to Oxiracetam’s ability to simulate the release of Protein Kinase C (PKC) in hippocampal cells, in both in vitro and in vivo studies. The theory is that this effect is a result of enhanced glutamate activity. PKC is a biochemical intermediate involved in long-term potentiation and memory formation.[11] In terms of the effects on hippocampal cells and PKC, an Oxiracetam dosage of 100mg/kg is comparable to a dose of 600mg/kg Alpha-GPC.[12]

Furthermore, Oxiracetam is active and effective in potentiating signaling at the AMPA glutamate receptor at a concentration range of 1-100µM, with a KD of 214+/-35nM. [13] Oxiracetam does not compete with or replace Aniracetam at AMPA receptor binding sites, indicating that it binds to different receptor sites.[14]

In terms of its effects on the glutamergic system, Oxiracetam tends to work as a positive AMPA modulator with a similar mechanism to Piracetam and Aniracetam. Oxiracetam does, however, have an additional benefit of increasing the release of glutamate, acetylcholine, and D-aspartic acid from activated neurons, and acts on different binding sites to Piracetam and Aniracetam. By a.) promoting increased glutamate release and b.) positively modulating glutamate receptors, Oxiracetam is able to increase metabolic activity and improve memory consolidation.[15]

Further Scientific research:

Please note that this is not a complete account of the scientific research on Oxiracetam to date. We have made a humble attempt to convey some of the most relevant research on the subject to date, in a variety of applications. However, there is far too much research to condense in this space. For more research, please select a topic and search through the hundreds of journal articles published in PubMed.

Clinical Reviews:

Despite being one of the first derivatives of Piracetam to be developed, there is a limited amount of clinical data on the effects of Oxiracetam. A number of reviews have examined the published studies on Oxiracetam and other racetam compounds, including a 2010 review published in Drugs Journal, in which Oxiracetam was classed as a subgroup 1 drug along with Piracetam, Aniracetam, Pramiracetam, and Phenylpiracetam. [16]

A meta-analysis of the pharmacokinetics of drugs for Alzheimer’s disease found that Oxiracetam crosses the blood-brain barrier effectively and persists in the CNS for longer than in the blood serum. [17] A 1994 review found that Oxiracetam had similar capabilities to other Piracetam-like Nootropics in terms of its ability to reverse amnesia. [18]

Human studies:

There have been a number of human clinical trials performed using Oxiracetam, especially to examine its effects on dementia and memory consolidation. In a 1992 study, 800mg of Oxiracetam was administered to patients with a neurodegenerative disease in a tablet form, twice daily for 12 weeks. 65 patients were enrolled, of whom 58 completed the study. A significant positive effect was observed in the data on the quality of life scale (using the Bonferroni technique) as well is in various neuropsychological tests. [19]

In 1993, a study was conducted on 12 healthy human volunteers, using a scopolamine model of amnesia. Following a baseline neuropsychological examinations, each participant was give either an Oxiracetam dosage of 800, 1600, or 2400mg, or placebo. 0.5mg of scopolamine hydrobromide was administered 1 hour later. The results indicated that oxiracetam improved overall test performance in verbal memory, semantic memory and attention tests. Oxiracetam had a significant benefit when compared to placebo, and a statistically significant increase in results at a dosage of 1600mg. [20]

A third study was performed in 1992, where a group of 96 patients who suffered from cognitive disorders were administered Oxiracetam at a dosage of 1600 mg/day for 26 weeks. After 6 months treatment, patients treated with Oxiracetam showed a statistically significant improvement in cognitive function and reaction time when compared to the placebo group. Tolerability was good for the duration of the treatment.[21]

Toxicity cases:

In the past, some patients have been withdrawn from clinical trials due to unwanted side effects and low tolerability.

For example, in 1989, a large-scale clinical study was conducted for 12 weeks on 307 patients who suffered from primary degenerative, multi-infarct or mixed forms of dementia. The patients were administered 800-mg tablets of Oxiracetam daily and assessed using the Inventory of Psychic and Somatic Complaints in the Elderly (IPCS-E) and by the Blessed Dementia Scale and Newcastle Memory, Information and Concentration Scale (NMICS). Of the 289 patients who were analyzed, 3 were withdrawn due to poor tolerability. [22]

Animal Studies:

Numerous animal studies have been conducted on this compound. Due to its well-established effects in animal models and the number of human clinical trials conducted on this compound, we have excluded animal studies from this description. For further information, please refer to PubMed.

References:

  • [1] Oxiracetam, PubChem, Open Chemistry Database, US National Library of Medicine, available online from https://pubchem.ncbi.nlm.nih.gov/compound/oxiracetam [Accessed 17 August, 2017]
  • [2] Malyke AG, Sadaie MR. (2010). Piracetam and Piracetam-Like Drugs. Drugs 70 (3): 287–312. PMID 20166767.
  • [3] Pellegata R, Pinza M, Pifferi G, Gaiti A, Mozzi R, Tirillini B, Porcellati G. (1981). Cyclic GABA-GABOB analogues. III - Synthesis and biochemical activity of new alkyl and acyl derivatives of 4-hydroxy-2-pyrrolidinone, Farmaco Sci, 36(10):845-55.
  • [4] Copani A, Genazzani AA, Aleppo G, Casabona G, Canonico PL, Scapagnini U, Nicoletti F. (1992). Nootropic drugs positively modulate alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid-sensitive glutamate receptors in neuronal cultures, J Neurochem, 58(4):1199-204.
  • [5] Marchi, M., Besana, E., Raiteri, M. (1990). Oxiracetam increases the release of endogenous glutamate from depolarized rat hippocampal slices, Eur J Pharmacol, 185(2-3):247-9.
  • [6] Gouliaev, A. H.; Senning, A. (1994). Piracetam and other structurally related nootropics. Brain Research Reviews, 19 (2): 180–222.
  • [7] Satoh, M. (1986). Aniracetam augments, and midazolam inhibits, the long-term potentiation in guinea-pig hippocampal slices, Neurosci Lett, 68(2):216-20.
  • [8] Oxiracetam, Examine.com, Unbiased Supplements Information, available online from https://examine.com/supplements/oxiracetam/ [Accessed August 17, 2017]
  • [9] Pugliese, A. M., Corradetti, R., Ballerini, L. and Pepeu, G. (1990). Effect of the nootropic drug oxiracetam on field potentials of rat hippocampal slices. British Journal of Pharmacology, 99: 189–193.
  • [10] Raiteri, M., Costa, R., Marchi, M. (1992). Effects of oxiracetam on neurotransmitter release from rat hippocampus slices and synaptosomes, Neurosci Lett, 145(1):109-13.
  • [11] Lucchi L, Pascale A, Battaini F, Govoni S, Trabucchi M. (1993). Cognition stimulating drugs modulate protein kinase C activity in cerebral cortex and hippocampus of adult rats, Life Sci, 53(24):1821-32.
  • [12] Fordyce DE, Clark VJ, Paylor R, Wehner JM. (1995). Enhancement of hippocampally-mediated learning and protein kinase C activity by oxiracetam in learning-impaired DBA/2 mice, Brain Res, 672(1-2):170-6.
  • [13] Nicoletti F, Casabona G, Genazzani AA, Copani A, Aleppo G, Canonico PL, Scapagnini U. (1992). Excitatory amino acids and neuronal plasticity: modulation of AMPA receptors as a novel substrate for the action of nootropic drugs, Funct Neurol, 7(5):413-22.
  • [14] Fallarino F, Genazzani AA, Silla S, L'Episcopo MR, Camici O, Corazzi L, Nicoletti F, Fioretti MC. (1995). [3H]aniracetam binds to specific recognition sites in brain membranes, J Neurochem, 65(2):912-8.
  • [15] Mondadori C, Classen W, Borkowski J, Ducret T, Buerki H, Schadé A. (1986). Effects of oxiracetam on learning and memory in animals: comparison with piracetam, Clin Neuropharmacol, 9 Suppl 3:S27-38.
  • [16] Malykh AG, Sadaie MR. (2010). Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders, Drugs, 70(3):287-312.
  • [17] Parnetti L. (1995). Clinical pharmacokinetics of drugs for Alzheimer's disease. Clin Pharmacokinet, 29(2):110-29.
  • [18] Gouliaev AH, Senning A. (1994). Piracetam and other structurally related Nootropics., Brain Res Brain Res Rev, 19(2):180-222.
  • [19] Bottini G, Vallar G, Cappa S, Monza GC, Scarpini E, Baron P, Cheldi A, Scarlato G. (1992). Oxiracetam in dementia: a double-blind, placebo-controlled study. Acta Neurol Scand, 86(3):237-41. ozzini R.degenerative dementia., available from:ibrary of Medicine, avilable ng sites, indicating that it binds to different re
  • [20] Preda L, Alberoni M, Bressi S, Cattaneo C, Parini J, Canal N, Franceschi M. (1993). Effects of acute doses of oxiracetam in the scopolamine model of human amnesia. Psychopharmacology (Berl), 110(4):421-6.
  • [21] Rozzini R, Zanetti O, Bianchetti A. (1992). Effectiveness of oxiracetam therapy in the treatment of cognitive deficiencies secondary to primary degenerative dementia, Acta Neurol (Napoli), 14(2):117-26.
  • [22] Maina G, et al. (1989). Oxiracetam in the treatment of primary degenerative and multi-infarct dementia: a double-blind, placebo-controlled study. Neuropsychobiology, 21(3):141-5.

Precaution and Disclaimer:

This Material is Sold For Research Use Only. Terms of Sale Apply. Not for Human Consumption, nor Medical, Veterinary, or Household Uses.

[Oxiracetam Q4 2017] Oxiracetam.170607.pdf

[Oxiracetam Q3 2012] Oxiracetam.20120905.pdf