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77191-36-7

77191-36-7 structure
77191-36-7 structure
  • Name: Nefiracetam
  • Chemical Name: N-(2,6-Dimethylphenyl)-2-(2-oxopyrrolidin-1-yl)acetamide
  • CAS Number: 77191-36-7
  • Molecular Formula: C14H18N2O2
  • Molecular Weight: 246.305
  • Catalog: API Nervous system medication Brain metabolism regulating drug
  • Create Date: 2018-07-21 12:05:09
  • Modify Date: 2025-08-20 11:07:56
  • 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].
Name N-(2,6-Dimethylphenyl)-2-(2-oxopyrrolidin-1-yl)acetamide
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-
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.
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

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
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
616-45-5 structure

616-45-5

1131-01-7 structure

1131-01-7

~87%

77191-36-7 structure

77191-36-7

Literature: Daiichi Pharmaceutical Co., Ltd. Patent: US5461157 A1, 1995 ;
Precursor  2

DownStream  0

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