Nefiracetam

Modify Date: 2024-01-04 12:25:22

Nefiracetam Structure
Nefiracetam structure
 Common Name Nefiracetam
CAS Number 77191-36-7 Molecular Weight 246.305
Density 1.2±0.1 g/cm3 Boiling Point 458.5±33.0 °C at 760 mmHg
Molecular Formula C14H18N2O2 Melting Point 151-155°C
MSDS Chinese USA Flash Point 231.1±25.4 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Nefiracetam


Nefiracetam is a GABAergic, cholinergic, and monoaminergic neuronal systems enhancer for Ro 5-4864-induced convulsions.Target: GABA ReceptorNefiracetam induces a short-term depression of ACh-evoked currents at submicromolar concentrations (0.01-0.1 μM) and a long-term enhancement of the currents at micromolar concentrations (1-10 μM). Nefiracetam interacts with PKA and PKC pathways, which may explain a cellular mechanism for the action of cognition-enhancing agents. Lower (submicromolar) concentrations of the nootropic Nefiracetam reduces ACh-evoked currents to 30% (0.01 μM) and 38% (0.1 μM) of control after a 10-minute treatment [1].Nefiracetam administered orally inhibits Ro 5-4864-induced convulsions in EL mice. Nefiracetam also efficiently inhibits Ro 5-4864-induced convulsions in DDY mice at doses higher than 10 mg/kg [2]. Nefiracetam administered daily 1 hour before each training session facilitates the acquisition process of the avoidance response [3].

 Names

Name N-(2,6-Dimethylphenyl)-2-(2-oxopyrrolidin-1-yl)acetamide
Synonym More Synonyms

 Nefiracetam Biological Activity

Description Nefiracetam is a GABAergic, cholinergic, and monoaminergic neuronal systems enhancer for Ro 5-4864-induced convulsions.Target: GABA ReceptorNefiracetam induces a short-term depression of ACh-evoked currents at submicromolar concentrations (0.01-0.1 μM) and a long-term enhancement of the currents at micromolar concentrations (1-10 μM). Nefiracetam interacts with PKA and PKC pathways, which may explain a cellular mechanism for the action of cognition-enhancing agents. Lower (submicromolar) concentrations of the nootropic Nefiracetam reduces ACh-evoked currents to 30% (0.01 μM) and 38% (0.1 μM) of control after a 10-minute treatment [1].Nefiracetam administered orally inhibits Ro 5-4864-induced convulsions in EL mice. Nefiracetam also efficiently inhibits Ro 5-4864-induced convulsions in DDY mice at doses higher than 10 mg/kg [2]. Nefiracetam administered daily 1 hour before each training session facilitates the acquisition process of the avoidance response [3].
Related Catalog
References

[1]. Nishizaki, T., et al., Nefiracetam modulates acetylcholine receptor currents via two different signal transduction pathways. Mol Pharmacol, 1998. 53(1): p. 1-5.

[2]. Shiotani, T., et al., Anticonvulsant actions of nefiracetam on epileptic EL mice and their relation to peripheral-type benzodiazepine receptors. Brain Res, 2000. 859(2): p. 255-61.

[3]. Sakurai, T., et al., Effects of N-(2,6-dimethylphenyl)-2-(2-oxo-1-pyrrolidinyl)acetamide (DM-9384) on learning and memory in rats. Jpn J Pharmacol, 1989. 50(1): p. 47-53.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 458.5±33.0 °C at 760 mmHg
Melting Point 151-155°C
Molecular Formula C14H18N2O2
Molecular Weight 246.305
Flash Point 231.1±25.4 °C
Exact Mass 246.136826
PSA 49.41000
LogP 1.53
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.594
Storage condition Store at RT

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UX9655650
CHEMICAL NAME :
1-Pyrrolidineacetamide, N-(2,6-dimethylphenyl)-2-oxo-
CAS REGISTRY NUMBER :
77191-36-7
LAST UPDATED :
199801
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C14-H18-N2-O2
MOLECULAR WEIGHT :
246.34

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1182 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - respiratory depression Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 44,211,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1940 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - respiratory depression Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 44,211,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>500 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - respiratory depression Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 44,211,1994 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
10920 mg/kg/13W-I
TOXIC EFFECTS :
Liver - other changes Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - other changes
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 44,214,1994
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
109 gm/kg/2Y-I
TOXIC EFFECTS :
Liver - changes in liver weight Kidney, Ureter, Bladder - proteinuria Kidney, Ureter, Bladder - other changes in urine composition
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 44,220,1994
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
16380 mg/kg/13W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - urine volume increased Kidney, Ureter, Bladder - other changes in urine composition
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 44,217,1994
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
32760 mg/kg/2Y-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - other changes in urine composition Nutritional and Gross Metabolic - changes in sodium
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 44,228,1994
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
8400 mg/kg/4W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - proteinuria Kidney, Ureter, Bladder - hematuria Kidney, Ureter, Bladder - inflammation, necrosis, or scarring of bladder
REFERENCE :
TOPADD Toxicologic Pathology. (c/o Dr. F.A. de la Iglesia, Warner-Lambert Co., Pharmaceutical Research Div., POB 1047, Ann Arbor, MI 48106) V.6(3/4)- 1978- Volume(issue)/page/year: 24,549,1996 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
11 gm/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 44,239,1994

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H319
Precautionary Statements P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn
Risk Phrases R22
RIDADR NONH for all modes of transport
RTECS UX9655650
HS Code 2933790090

 Synthetic Route

2-Pyrrolidinone structure

2-Pyrrolidinone

CAS#:616-45-5

2-Chloro-N-(2,6-dimethylphenyl)acetamide structure

2-Chloro-N-(2,6...

CAS#:1131-01-7

~87%

Nefiracetam Structure

Nefiracetam

CAS#:77191-36-7

Literature: Daiichi Pharmaceutical Co., Ltd. Patent: US5461157 A1, 1995 ;

 Precursor & DownStream

Precursor  2

DownStream  0

 Customs

HS Code 2933790090
Summary 2933790090. other lactams. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:9.0%. General tariff:20.0%

 Articles28

More Articles
Investigation on urinary proteins and renal mRNA expression in canine renal papillary necrosis induced by nefiracetam.

Arch. Toxicol. 79(9) , 500-7, (2005)

The occurrence of renal papillary necrosis (RPN), seen only in dogs after repeated oral administration of nefiracetam, a neurotransmission enhancer, at a relatively high dose, is because of inhibition...

Nefiracetam and galantamine modulation of excitatory and inhibitory synaptic transmission via stimulation of neuronal nicotinic acetylcholine receptors in rat cortical neurons.

Neuroscience 160(2) , 484-91, (2009)

The cholinergic and glutamatergic systems are known to be downregulated in the brain of Alzheimer's disease patients. Galantamine and nefiracetam have been shown to potentiate the phasic activity of n...

Anticonvulsant properties of the novel nootropic agent nefiracetam in seizure models of mice and rats.

Epilepsia 46(6) , 811-8, (2005)

Nefiracetam (NEF) is a novel pyrrolidone-type nootropic agent, and it has been reported to possess various pharmacologic effects as well as cognition-enhancing effects. The present study focused on th...

 Synonyms

N-(2,6-dimethylphenyl)-2-(2-oxopyrrolidin-1-yl)acetamide
Nefiracetam
MFCD00209882
Dmmpa
2-(2-Oxo-1-pyrrolidinyl)-N-(2,6-dimethylphenyl)acetamide
N-(2,6-Dimethylphenyl)-2-(2-oxo-1-pyrrolidinyl)acetamide
1-Pyrrolidineacetamide, N-(2,6-dimethylphenyl)-2-oxo-
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Related Compounds: More...
Nefiracetam D-2
123941-02-6
Chemsrc provides Nefiracetam(CAS#:77191-36-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Nefiracetam are included as well.>> amp version: Nefiracetam

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