Nefiracetam

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Names

[ Name ]:
Nefiracetam

[Synonym ]:
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-

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

MSDS

Click to get detail MSDS

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

[ 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

Click to get detail synthetic route

Precursor & DownStream

Precursor

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

DownStream

Customs

[ HS Code ]: 2933790090

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

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...