Nefiracetam | CAS#77191-36-7 | GABA receptor agonist

MedKoo Cat#: 529303 | Name: Nefiracetam

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Description:

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

Nefiracetam is a GABA receptor agonist potentially for the treatment of epilepsy.

Chemical Structure

Nefiracetam

CAS#77191-36-7

Theoretical Analysis

MedKoo Cat#: 529303

Name: Nefiracetam

CAS#: 77191-36-7

Chemical Formula: C14H18N2O2

Exact Mass: 246.1368

Molecular Weight: 246.31

Elemental Analysis: C, 68.27; H, 7.37; N, 11.37; O, 12.99

Price and Availability

Size	Price	Availability	Quantity
200mg	USD 280.00
1g	USD 680.00

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Related CAS #

No Data

Synonym

DM-9384; DZL-221; DM9384; DZL221; DM 9384; DZL 221

IUPAC/Chemical Name

N-(2,6-dimethylphenyl)-2-(2-oxopyrrolidin-1-yl)acetamide

InChi Key

NGHTXZCKLWZPGK-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H18N2O2/c1-10-5-3-6-11(2)14(10)15-12(17)9-16-8-4-7-13(16)18/h3,5-6H,4,7-9H2,1-2H3,(H,15,17)

SMILES Code

O=C(NC1=C(C)C=CC=C1C)CN2C(CCC2)=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:

Nefiracetam is a GABAergic, cholinergic, and monoaminergic neuronal systems enhancer for Ro 5-4864-induced convulsions.

In vitro activity:

Nefiracetam induced a short-term depression of ACh-evoked currents at submicromolar concentrations (0.01-0.1 microM) and a long-term enhancement of the currents at micromolar concentrations (1-10 microM). The depression was caused by activation of pertussis toxin-sensitive, G protein-regulated, cAMP-dependent protein kinase (PKA) with subsequent phosphorylation of the ACh receptors; in contrast, the enhancement was caused by activation of Ca(2+)-dependent protein kinase C (PKC) and the ensuing PKC phosphorylation of the receptors. Reference: Mol Pharmacol. 1998 Jan;53(1):1-5. https://pubmed.ncbi.nlm.nih.gov/9443926/

In vivo activity:

Nefiracetam, when administered orally to EL mice, inhibited convulsions induced by the PBR agonist, Ro 5-4864, with an ED(50) of 17.2 mg/kg, whereas it did not inhibit the drug-induced convulsions in control DDY mice. When administered intravenously (i.v.) to DDY mice, nefiracetam and other piracetam-like nootropics inhibited the Ro 5-4864-induced convulsions in the sequence of nefiracetam>aniracetam>>oxiracetam, piracetam. Reference: Brain Res. 2000 Mar 24;859(2):255-61. https://pubmed.ncbi.nlm.nih.gov/10719072/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	121.80
	DMF:PBS (pH 7.2) (1:1)	0.5	2.03
	DMSO	47.2	191.46
	Ethanol	31.2	126.71
	Water	14.0	56.84

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 246.31 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. Nishizaki T, Matsuoka T, Nomura T, Sumikawa K, Shiotani T, Watabe S, Yoshii M. Nefiracetam modulates acetylcholine receptor currents via two different signal transduction pathways. Mol Pharmacol. 1998 Jan;53(1):1-5. doi: 10.1124/mol.53.1.1. PMID: 9443926. 2. Yoshii M, Watabe S. Enhancement of neuronal calcium channel currents by the nootropic agent, nefiracetam (DM-9384), in NG108-15 cells. Brain Res. 1994 Apr 11;642(1-2):123-31. doi: 10.1016/0006-8993(94)90913-x. PMID: 8032872. 3. Ueda M, Fujita R, Koji T, Ueda H. The cognition-enhancer nefiracetam inhibits both necrosis and apoptosis in retinal ischemic models in vitro and in vivo. J Pharmacol Exp Ther. 2004 Apr;309(1):200-7. doi: 10.1124/jpet.103.061127. Epub 2004 Jan 12. PMID: 14718588. 4. Shiotani T, Nakamoto Y, Watabe S, Yoshii M, Nabeshima T. Anticonvulsant actions of nefiracetam on epileptic EL mice and their relation to peripheral-type benzodiazepine receptors. Brain Res. 2000 Mar 24;859(2):255-61. doi: 10.1016/s0006-8993(00)01971-5. PMID: 10719072.

In vitro protocol:

In vivo protocol:

1. Ueda M, Fujita R, Koji T, Ueda H. The cognition-enhancer nefiracetam inhibits both necrosis and apoptosis in retinal ischemic models in vitro and in vivo. J Pharmacol Exp Ther. 2004 Apr;309(1):200-7. doi: 10.1124/jpet.103.061127. Epub 2004 Jan 12. PMID: 14718588. 2. Shiotani T, Nakamoto Y, Watabe S, Yoshii M, Nabeshima T. Anticonvulsant actions of nefiracetam on epileptic EL mice and their relation to peripheral-type benzodiazepine receptors. Brain Res. 2000 Mar 24;859(2):255-61. doi: 10.1016/s0006-8993(00)01971-5. PMID: 10719072.

1: Omotuyi OI, Ueda H. Molecular dynamics study-based mechanism of nefiracetam-induced NMDA receptor potentiation. Comput Biol Chem. 2015 Apr;55:14-22. doi: 10.1016/j.compbiolchem.2015.01.004. PubMed PMID: 25659913. 2: Starkstein SE, Brockman S, Hatch KK, Bruce DG, Almeida OP, Davis WA, Robinson RG. A Randomized, Placebo-Controlled, Double-Blind Efficacy Study of Nefiracetam to Treat Poststroke Apathy. J Stroke Cerebrovasc Dis. 2016 May;25(5):1119-27. doi: 10.1016/j.jstrokecerebrovasdis.2016.01.032. PubMed PMID: 26915605. 3: Moriguchi S, Han F, Shioda N, Yamamoto Y, Nakajima T, Nakagawasai O, Tadano T, Yeh JZ, Narahashi T, Fukunaga K. Nefiracetam activation of CaM kinase II and protein kinase C mediated by NMDA and metabotropic glutamate receptors in olfactory bulbectomized mice. J Neurochem. 2009 Jul;110(1):170-81. doi: 10.1111/j.1471-4159.2009.06122.x. PubMed PMID: 19457128. 4: Moriguchi S, Zhao X, Marszalec W, Yeh JZ, Fukunaga K, Narahashi T. Nefiracetam and galantamine modulation of excitatory and inhibitory synaptic transmission via stimulation of neuronal nicotinic acetylcholine receptors in rat cortical neurons. Neuroscience. 2009 May 5;160(2):484-91. doi: 10.1016/j.neuroscience.2009.02.055. PubMed PMID: 19272425. 5: Moriguchi S, Shioda N, Han F, Narahashi T, Fukunaga K. CaM kinase II and protein kinase C activations mediate enhancement of long-term potentiation by nefiracetam in the rat hippocampal CA1 region. J Neurochem. 2008 Aug;106(3):1092-103. doi: 10.1111/j.1471-4159.2008.05440.x. PubMed PMID: 18445137. 6: Moriguchi S, Shioda N, Maejima H, Zhao X, Marszalec W, Yeh JZ, Fukunaga K, Narahashi T. Nefiracetam potentiates N-methyl-D-aspartate (NMDA) receptor function via protein kinase C activation and reduces magnesium block of NMDA receptor. Mol Pharmacol. 2007 Feb;71(2):580-7. PubMed PMID: 17095583. 7: Robinson RG, Jorge RE, Clarence-Smith K. Double-blind randomized treatment of poststroke depression using nefiracetam. J Neuropsychiatry Clin Neurosci. 2008 Spring;20(2):178-84. doi: 10.1176/appi.neuropsych.20.2.178. PubMed PMID: 18451188. 8: Fu CY, He XY, Li XF, Zhang X, Huang ZW, Li J, Chen M, Duan CZ. Nefiracetam Attenuates Pro-Inflammatory Cytokines and GABA Transporter in Specific Brain Regions of Rats with Post-Ischemic Seizures. Cell Physiol Biochem. 2015;37(5):2023-31. doi: 10.1159/000438562. PubMed PMID: 26584300. 9: Robinson RG, Jorge RE, Clarence-Smith K, Starkstein S. Double-blind treatment of apathy in patients with poststroke depression using nefiracetam. J Neuropsychiatry Clin Neurosci. 2009 Spring;21(2):144-51. doi: 10.1176/appi.neuropsych.21.2.144. PubMed PMID: 19622685. 10: Han F, Nakano T, Yamamoto Y, Shioda N, Lu YM, Fukunaga K. Improvement of depressive behaviors by nefiracetam is associated with activation of CaM kinases in olfactory bulbectomized mice. Brain Res. 2009 Apr 10;1265:205-14. doi: 10.1016/j.brainres.2009.02.014. PubMed PMID: 19233146. 11: Kitano Y, Komiyama C, Makino M, Takasuna K, Satoh H, Aoki T, Kinoshita M, Takazawa A, Yamauchi T, Sakurada S. Anticonvulsant and neuroprotective effects of the novel nootropic agent nefiracetam on kainic acid-induced seizures in rats. Brain Res. 2005 Sep 28;1057(1-2):168-76. PubMed PMID: 16122714. 12: Lu XC, Dave JR, Chen Z, Cao Y, Liao Z, Tortella FC. Nefiracetam attenuates post-ischemic nonconvulsive seizures in rats and protects neuronal cell death induced by veratridine and glutamate. Life Sci. 2013 Jun 13;92(22):1055-63. doi: 10.1016/j.lfs.2013.04.004. PubMed PMID: 23603142. 13: Tsuchiya Y, Yabe K, Takada S, Ishii Y, Jindo T, Furuhama K, Suzuki KT. Early pathophysiological features in canine renal papillary necrosis induced by nefiracetam. Toxicol Pathol. 2005;33(5):561-9. PubMed PMID: 16105799. 14: Ando T, Takagi N, Takagi K, Kago T, Takeo S. Effects of nefiracetam on the levels of brain-derived neurotrophic factor and synapsin I mRNA and protein in the hippocampus of microsphere-embolized rats. Eur J Pharmacol. 2005 Jan 10;507(1-3):49-56. PubMed PMID: 15659294. 15: Yoshii M, Furukawa T, Ogihara Y, Watabe S, Shiotani T, Ishikawa Y, Nishimura M, Nukada T. Negative regulation of opioid receptor-G protein-Ca2+ channel pathway by the nootropic nefiracetam. Ann N Y Acad Sci. 2004 Oct;1025:389-97. PubMed PMID: 15542741. 16: Moriguchi S, Marszalec W, Zhao X, Yeh JZ, Narahashi T. Potentiation of N-methyl-D-aspartate-induced currents by the nootropic drug nefiracetam in rat cortical neurons. J Pharmacol Exp Ther. 2003 Oct;307(1):160-7. PubMed PMID: 12805478. 17: Woodruff-Pak DS, Ewers M, Shiotani T, Watabe S, Tanaka M, Wenk GL. Nefiracetam and physostigmine: separate and combined effects on learning in older rabbits. Neurobiol Aging. 2004 Jul;25(6):807-16. PubMed PMID: 15165705. 18: Yan Y, Mizuno T, Nitta A, Yamada K, Nabeshima T. Nefiracetam attenuates methamphetamine-induced discriminative stimulus effects in rats. Ann N Y Acad Sci. 2004 Oct;1025:274-8. PubMed PMID: 15542727. 19: Takeo S, Fukatsu T, Miyake-Takagi K, Takagi N, Niimura M, Nagakura A, Ando T, Tanonaka K. Persistent effects of delayed treatment with nefiracetam on the water maze task in rats with sustained cerebral ischemia. J Pharmacol Exp Ther. 2003 Feb;304(2):513-23. PubMed PMID: 12538802. 20: Tsuchiya Y, Tominaga Y, Matsubayashi K, Jindo T, Furuhama K, Suzuki KT. Investigation on urinary proteins and renal mRNA expression in canine renal papillary necrosis induced by nefiracetam. Arch Toxicol. 2005 Sep;79(9):500-7. PubMed PMID: 16007418.