CAS No.77191-36-7,Nefiracetam Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	77191-36-7
Name:	Nefiracetam
Article Data:	3

Formula:	C₁₄H₁₈N₂O₂
Molecular Weight:	246.309
Synonyms:	2-(2-Oxo-1-pyrrolidinyl)-N-(2,6-dimethylphenyl)acetamide;DM 9384;DMMPA;DMPPA;DZL 221;N-(2,6-Dimethylphenyl)-2-(2-oxo-1-pyrrolidinyl)acetamide;Translon;
EINECS:	636-080-4
Density:	1.187 g/cm³
Melting Point:	151-155 °C
Boiling Point:	458.5 °C at 760 mmHg
Flash Point:	231.1 °C
Appearance:	white to off-white crystalline powder
Hazard Symbols:	Xn
Risk Codes:	22
PSA:	49.41000
LogP:	1.87520

Synthetic route

: 50-00-0
formaldehyd

: 119072-54-7, 2769-71-3
2,6-dimethylphenyl isonitrile

: 56-12-2
4-amino-n-butyric acid

: 77191-36-7
nefiracetam

Conditions

Conditions	Yield
In 2,2,2-trifluoroethanol at 40℃; for 24h; Ugi Condensation; Inert atmosphere;	39%

...Expand

: 616-45-5
2-pyrrolidinon

: 1131-01-7
2-chloro-N-(2,6-dimethylphenyl)acetamide

: 77191-36-7
nefiracetam

Conditions

Conditions	Yield
In nitrogen; water; toluene	22.2 g (90%)
With sodium methylate In water; toluene	332 g (90%)
In nitrogen; water; toluene	22.4 g (91%)
In tert-butyl methyl ether; nitrogen; water	2.19 g (89%)

: C9H11N3O2

: 87-62-7
2,6-dimethylaniline

: 77191-36-7
nefiracetam

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	24 g

: 67969-82-8
tetrafluoroboric acid diethyl ether

: 13755-29-8
sodium tetrafluoroborate

: 2362-50-7
thianthrene-5-oxide

: 77191-36-7
nefiracetam

: C26H25N2O2S2(1+)*BF4(1-)

Conditions

Conditions	Yield
Stage #1: tetrafluoroboric acid diethyl ether; thianthrene-5-oxide; nefiracetam With trifluoroacetic anhydride In acetonitrile at -40 - 25℃; for 6h; Schlenk technique; Stage #2: sodium tetrafluoroborate In dichloromethane; water	74%

...Expand

: 2,3,7,8-tetrafluorothianthrene-S-oxide

: 77191-36-7
nefiracetam

: C26H21F4N2O2S2(1+)

Conditions

Conditions	Yield
With 2,3,7,8-tetrafluorothianthrene; boron trifluoride diethyl etherate; trifluoroacetic anhydride In acetonitrile at 0 - 25℃; regioselective reaction;	63%

: 2,3,7,8-tetrafluorothianthrene-S-oxide

: 77191-36-7
nefiracetam

: C26H21F4N2O2S2(1+)*F6P(1-)

Conditions

Conditions	Yield
Stage #1: 2,3,7,8-tetrafluorothianthrene-S-oxide; nefiracetam With boron trifluoride diethyl etherate; trifluoroacetic anhydride In acetonitrile at 0 - 25℃; for 4h; Sealed tube; Stage #2: With ammonium hexafluorophosphate In dichloromethane; water	63%

: 77191-36-7
nefiracetam

A: 5-Hydroxynefiracetam

B: N-(2-hydroxymethyl-6-methyl-phenyl)-2-(2-oxo-pyrrolidin-1-yl)-acetamide

C: 4'-hydroxy-nefiracetam

D: 3'-hydroxy-nefiracetam

Conditions

Conditions	Yield
With NADPH-generating system; rat liver microsome In water at 37℃; for 0.25h; pH=7.4; Enzyme kinetics; Oxidation;

...Expand

: 77191-36-7
nefiracetam

A: 3-mesyloxy-nefiracetam

B: 4-mesyloxy-nefiracetam

Conditions

Conditions	Yield
With bis(methanesulfonyl)peroxide at 23℃; for 24h; Inert atmosphere; Schlenk technique; Overall yield = 65%; Overall yield = 112 mg;	A 39 %Spectr. B 26 %Spectr.

: 77191-36-7
nefiracetam

: C19H22N4O2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic anhydride / acetonitrile / 6 h / -40 - 25 °C / Schlenk technique 2: [(2-di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 16 h / 70 °C / Inert atmosphere; Glovebox; Sealed tube View Scheme

: 77191-36-7
nefiracetam

: C22H21N3O4

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic anhydride / acetonitrile / 6 h / -40 - 25 °C / Schlenk technique 2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; tetrakis(acetonitrile)copper(I)tetrafluoroborate; tetramethyl ammoniumhydroxide / acetonitrile; dimethyl sulfoxide / 8 h / 15 °C / Inert atmosphere; Irradiation View Scheme

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Specification

The Nefiracetam is an organic compound with the formula C₁₄H₁₈N₂O₂. The IUPAC name of this chemical is N-(2,6-dimethylphenyl)-2-(2-oxopyrrolidin-1-yl)acetamide. With the CAS registry number 77191-36-7, it is also named as 2-(2-Oxo-1-pyrrolidinyl)-N-(2,6-dimethylphenyl)acetamide. The product's classification codes are Central nervous system agents; Drug / Therapeutic Agent; Neuroprotective Agents; Nootropic agents; Protective Agents; Psychotropic drugs; Reproductive Effect. Besides, its cytoprotective actions are mediated by enhancement of GABAergic, cholinergic, and monoaminergic neuronal systems that give antiamnesia effects to the Alzheimer's type and cerebrovascular type of dementia.

Physical properties about Nefiracetam are: (1)ACD/LogP: 1.53; (2)ACD/LogD (pH 5.5): 1.53; (3)ACD/LogD (pH 7.4): 1.53; (4)ACD/BCF (pH 5.5): 8.53; (5)ACD/BCF (pH 7.4): 8.53; (6)ACD/KOC (pH 5.5): 161.45; (7)ACD/KOC (pH 7.4): 161.47; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 40.62 Å²; (12)Index of Refraction: 1.593; (13)Molar Refractivity: 70.33 cm³; (14)Molar Volume: 207.3 cm³; (15)Polarizability: 27.88×10^-24cm³; (16)Surface Tension: 51.6 dyne/cm; (17)Density: 1.187 g/cm³; (18)Flash Point: 231.1 °C; (19)Enthalpy of Vaporization: 71.88 kJ/mol; (20)Boiling Point: 458.5 °C at 760 mmHg; (21)Vapour Pressure: 1.36E-08 mmHg at 25°C.

Preparation: this chemical can be prepared by 1 - (hydroxy methyl) -2-- pyrrolidine ketone and 2,6 - dimethylaniline. The yield is about 76%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2N(CC(=O)Nc1c(cccc1C)C)CCC2
(2)InChI: InChI=1/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)
(3)InChIKey: NGHTXZCKLWZPGK-UHFFFAOYAF
(4)Std. InChI: 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)
(5)Std. InChIKey: NGHTXZCKLWZPGK-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	oral	> 500mg/kg (500mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Arzneimittel-Forschung. Drug Research. Vol. 44, Pg. 211, 1994.
mouse	LD50	intravenous	421mg/kg (421mg/kg)		United States Patent Document. Vol. #4341790,
mouse	LD50	oral	1766mg/kg (1766mg/kg)		United States Patent Document. Vol. #4341790,
rat	LD50	oral	1182mg/kg (1182mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Arzneimittel-Forschung. Drug Research. Vol. 44, Pg. 211, 1994.