Oxiracetam | CAS#62613-82-5 | AMPA receptor modulator

MedKoo Cat#: 561592 | Name: Oxiracetam

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oxiracetam is a positive allosteric modulator of the AMPA receptors. It improves hippocampally-mediated learning performance by increasing membrane-bound protein kinase C (PKC). It is also considered a nootropic drug with very mild stimulant effect.

Chemical Structure

Oxiracetam

CAS#62613-82-5

Theoretical Analysis

MedKoo Cat#: 561592

Name: Oxiracetam

CAS#: 62613-82-5

Chemical Formula: C6H10N2O3

Exact Mass: 158.0691

Molecular Weight: 158.16

Elemental Analysis: C, 45.57; H, 6.37; N, 17.71; O, 30.35

Price and Availability

Size	Price	Availability
1g	USD 150.00	2 Weeks
2g	USD 250.00	2 Weeks
5g	USD 550.00	2 Weeks
10g	USD 950.00	2 Weeks
25g	USD 1,650.00	2 Weeks
100g	USD 2,750.00	2 Weeks

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Synonym

Oxiracetam; ISF-2522; Neuractiv; Hydroxypiracetam;

IUPAC/Chemical Name

4-Hydroxy-2-oxopyrrolidine-N-acetamide

InChi Key

IHLAQQPQKRMGSS-UHFFFAOYSA-N

InChi Code

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

SMILES Code

O=C(N)CN1C(CC(O)C1)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oxiracetam is a cyclic derivative of γ-aminobutyric acid (GABA).

In vitro activity:

This study used quantitative reverse transcription polymerase chain reaction to assess the inhibitory effects of ORC (oxiracetam) on Aβ-induced mRNA levels of interleukin-1β (IL-1β), IL-6, and tumor necrosis factor-α (TNF-α); enzyme-linked immunosorbent assay was used to examine the productions of these cytokines. ORC prevented the Aβ-induced activation of BV2 cells, as reflected by reduced morphological changes and phagocytic ability. In addition, ORC downregulated the expression of Aβ-induced cytokines (IL-1β, IL-6, and TNF-α) and the production of NO in BV2 cells. Furthermore, ORC protected HT22 cells from indirect damage evoked by Aβ-treated BV2 cell-conditioned medium, but not from direct Aβ-induced toxicity. Reference: Front Neurol. 2020 Jul 17;11:623. https://pubmed.ncbi.nlm.nih.gov/32765394/

In vivo activity:

In this study first identified that (S)-oxiracetam, but not (R)-oxiracetam, was the effective ingredient that alleviated the impairments of spatial learning and memory by ameliorating neuron damage and white matter lesions, increasing the cerebral blood flow, and inhibiting astrocyte activation in chronic cerebral hypoperfused rats. Furthermore, using MALDI-MSI and LC-MS/MS, this study demonstrated that (S)-oxiracetam regulated ATP metabolism, glutamine-glutamate and anti-oxidants in the cortex region of hypoperfused rats. Reference: Sci Rep. 2017 Aug 30;7(1):10052. https://pubmed.ncbi.nlm.nih.gov/28855592/

	Solvent	mg/mL	mM
Solubility
	Ethanol	16.7	105.59
	PBS (pH 7.2)	10.0	63.23
	Water	65.5	414.15

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 158.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Zhang H, Jia L, Jia J. Oxiracetam Offers Neuroprotection by Reducing Amyloid β-Induced Microglial Activation and Inflammation in Alzheimer's Disease. Front Neurol. 2020 Jul 17;11:623. doi: 10.3389/fneur.2020.00623. PMID: 32765394; PMCID: PMC7380077. 2. Li W, Liu H, Jiang H, Wang C, Guo Y, Sun Y, Zhao X, Xiong X, Zhang X, Zhang K, Nie Z, Pu X. (S)-Oxiracetam is the Active Ingredient in Oxiracetam that Alleviates the Cognitive Impairment Induced by Chronic Cerebral Hypoperfusion in Rats. Sci Rep. 2017 Aug 30;7(1):10052. doi: 10.1038/s41598-017-10283-4. PMID: 28855592; PMCID: PMC5577264. 3. Sansone M, Castellano C, Ammassari-Teule M. Improvement of avoidance acquisition by the nootropic drug oxiracetam in mice. Arch Int Pharmacodyn Ther. 1985 May;275(1):86-92. PMID: 2862852.

In vitro protocol:

In vivo protocol:

1. Li W, Liu H, Jiang H, Wang C, Guo Y, Sun Y, Zhao X, Xiong X, Zhang X, Zhang K, Nie Z, Pu X. (S)-Oxiracetam is the Active Ingredient in Oxiracetam that Alleviates the Cognitive Impairment Induced by Chronic Cerebral Hypoperfusion in Rats. Sci Rep. 2017 Aug 30;7(1):10052. doi: 10.1038/s41598-017-10283-4. PMID: 28855592; PMCID: PMC5577264. 2. Sansone M, Castellano C, Ammassari-Teule M. Improvement of avoidance acquisition by the nootropic drug oxiracetam in mice. Arch Int Pharmacodyn Ther. 1985 May;275(1):86-92. PMID: 2862852.

1: Hu S, Shi J, Xiong W, Li W, Fang L, Feng H. Oxiracetam or fastigial nucleus stimulation reduces cognitive injury at high altitude. Brain Behav. 2017 Aug 23;7(10):e00762. doi: 10.1002/brb3.762. eCollection 2017 Oct. PubMed PMID: 29075554; PubMed Central PMCID: PMC5651378. 2: Jiang JJ, Xie YM, Zhang Y, Zhang YK, Wang ZM, Han B. [Clinical medication characteristics of Shuxuening injection in treatment of cerebral infarction research based on registration]. Zhongguo Zhong Yao Za Zhi. 2016 Dec;41(24):4516-4520. doi: 10.4268/cjcmm20162407. Chinese. PubMed PMID: 28936832. 3: Li W, Liu H, Jiang H, Wang C, Guo Y, Sun Y, Zhao X, Xiong X, Zhang X, Zhang K, Nie Z, Pu X. (S)-Oxiracetam is the Active Ingredient in Oxiracetam that Alleviates the Cognitive Impairment Induced by Chronic Cerebral Hypoperfusion in Rats. Sci Rep. 2017 Aug 30;7(1):10052. doi: 10.1038/s41598-017-10283-4. PubMed PMID: 28855592; PubMed Central PMCID: PMC5577264. 4: Huang L, Shang E, Fan W, Li X, Li B, He S, Fu Y, Zhang Y, Li Y, Fang W. S-oxiracetam protect against ischemic stroke via alleviating blood brain barrier dysfunction in rats. Eur J Pharm Sci. 2017 Nov 15;109:40-47. doi: 10.1016/j.ejps.2017.07.029. Epub 2017 Jul 29. PubMed PMID: 28760594. 5: Chen F, Peng J, Liu S, Peng H, Pan Z, Bu L, Xiao H, Zhang R. The fluorescence and resonance Rayleigh scattering spectra study on the interactions of palladium (II)-Nootropic chelate with Congo red and their analytical applications. Spectrochim Acta A Mol Biomol Spectrosc. 2017 Apr 15;177:41-48. doi: 10.1016/j.saa.2017.01.027. Epub 2017 Jan 16. PubMed PMID: 28122287. 6: Yao XL, Yao ZH, Li L, Nie L, Zhang SF. Oxiracetam can improve cognitive impairment after chronic cerebral hypoperfusion in rats. Psychiatry Res. 2016 Dec 30;246:284-292. doi: 10.1016/j.psychres.2016.10.006. Epub 2016 Oct 4. PubMed PMID: 27741481. 7: Wang W, Ji H, Li T, Jia Y, Xie H. Pharmacokinetic comparisons of S-oxiracetam and R-oxiracetam in beagle dogs. Acta Pharm. 2016 Jun 1;66(2):279-87. doi: 10.1515/acph-2016-0013. PubMed PMID: 27279070. 8: Zhang Q, Yang W, Zhang Q, Yang Y, Li J, Lu Y, Zheng Y, He J, Zhao D, Chen X. Enantioselective HPLC determination of oxiracetam enantiomers and application to a pharmacokinetic study in beagle dogs. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jul 1;993-994:9-13. doi: 10.1016/j.jchromb.2015.04.033. Epub 2015 Apr 30. PubMed PMID: 25978861. 9: Chen J, Zhou SN, Zhang YM, Feng YL, Wang S. Glycosides of cistanche improve learning and memory in the rat model of vascular dementia. Eur Rev Med Pharmacol Sci. 2015 Apr;19(7):1234-40. PubMed PMID: 25912583. 10: Zhang Q, Yang W, Yang Y, Xing H, Zhang Q, Li J, Lu Y, He J, Yang S, Zhao D, Chen X. Comparative pharmacokinetic studies of racemic oxiracetam and its pure enantiomers after oral administration in rats by a stereoselective HPLC method. J Pharm Biomed Anal. 2015;111:153-8. doi: 10.1016/j.jpba.2015.03.039. Epub 2015 Apr 4. PubMed PMID: 25886392. 11: Cui JF, Yang W, Xie YM, Sun Y, Zhuang Y, Wang YY. [Real-world analysis of concurrent diseases and medicine use among patients with insomnia]. Zhongguo Zhong Yao Za Zhi. 2014 Sep;39(18):3519-26. Chinese. PubMed PMID: 25532388. 12: Wang C, Li F, Guan Y, Zhu L, Fei Y, Zhang J, Pan Y. Bone marrow stromal cells combined with oxiracetam influences the expression of B-cell lymphoma 2 in rats with ischemic stroke. J Stroke Cerebrovasc Dis. 2014 Nov-Dec;23(10):2591-7. doi: 10.1016/j.jstrokecerebrovasdis.2014.05.035. Epub 2014 Sep 26. PubMed PMID: 25267587. 13: Wang D, Wu S. Development and validation of a RP-HPLC method for the simultaneous determination of aceglutamide and oxiracetam in an injection formulation. J Chromatogr Sci. 2015 May-Jun;53(5):767-70. doi: 10.1093/chromsci/bmu123. Epub 2014 Sep 19. PubMed PMID: 25238766. 14: Wan X, Wang H, Ma P, Xi L, Sun J, He Z, Zhang X, Liu X. Simultaneous determination of oxiracetam and its degraded substance in rat plasma by HPLC-MS/MS and its application to pharmacokinetic study after a single high-dose intravenous administration. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Oct 15;969:95-100. doi: 10.1016/j.jchromb.2014.07.041. Epub 2014 Aug 4. PubMed PMID: 25168792. 15: Pace V, Rae JP, Procter DJ. Cu(I)-NHC catalyzed asymmetric silyl transfer to unsaturated lactams and amides. Org Lett. 2014 Jan 17;16(2):476-9. doi: 10.1021/ol4033623. Epub 2013 Dec 18. PubMed PMID: 24350760. 16: Wan D, Xue L, Zhu H, Luo Y. Catalpol Induces Neuroprotection and Prevents Memory Dysfunction through the Cholinergic System and BDNF. Evid Based Complement Alternat Med. 2013;2013:134852. doi: 10.1155/2013/134852. Epub 2013 Sep 8. PubMed PMID: 24194776; PubMed Central PMCID: PMC3782139. 17: Li JW, Yang DJ, Chen XY, Liang HQ. [Protective effect of oxiracetam on traumatic brain injury in rats]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2013 Jul;29(4):298-300. Chinese. PubMed PMID: 24175546. 18: Lee DS, Ryu HJ, Kim JE, Choi HC, Kim YI, Song HK, Kang TC. The effect of levetiracetam on status epilepticus-induced neuronal death in the rat hippocampus. Seizure. 2013 Jun;22(5):368-77. doi: 10.1016/j.seizure.2013.02.005. Epub 2013 Mar 13. PubMed PMID: 23490457. 19: Ma W, Xu H, Liu Z, Ning F. [Optimization of preparation of poly ( glycidyl methacrylate-divinylbenzene) monolithic column with orthogonal experiments for separation of small molecules]. Se Pu. 2010 Feb;28(2):175-9. Chinese. PubMed PMID: 20556957. 20: Wang X, Zhu J, Xu R, Yang X, Wu H, Lin D, Ye F, Hu L. Determination of piracetam in rat plasma by LC-MS/MS and its application to pharmacokinetics. Biomed Chromatogr. 2010 Oct;24(10):1108-12. doi: 10.1002/bmc.1412. 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