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Flumazenil

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Name

Flumazenil

EINECS 616-650-9
CAS No. 78755-81-4 Density 1.39 g/cm3
PSA 64.43000 LogP 1.71160
Solubility 128 mg/L in water Melting Point 201-203 °C
Formula C15H14FN3O3 Boiling Point 528 °C at 760 mmHg
Molecular Weight 303.293 Flash Point 273.1 °C
Transport Information N/A Appearance Colourless crystals
Safety 26-27-36/37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 78755-81-4 (Flumazenil) Hazard Symbols IrritantXi
Synonyms

Anexate;Flumazepil;Flumazenil [USAN:BAN:INN];Romazicon;Flumazenilum [Latin];Flumazenil (JAN/USP);Romazicon (TN);4H-Imidazo[1,5-a][1,4]benzodiazepine-3- carboxylic acid,8-fluoro-5,6-dihydro-5- methyl-6-oxo-,ethyl ester;Flumazenilo;Lanexat;Ethyl 8-fluoro-5-methyl-5,6-dihydro-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylate;4H-Imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylic acid, 8-fluoro-5,6-dihydro-5-methyl-6-oxo-, ethyl ester;Ethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylate;

Article Data 12

Flumazenil Synthetic route

428507-28-2

(E)-(dimethylamino-methyleneamino)-acetic acid ethyl ester

193693-31-1

2-chloro-7-fluoro-4-methyl-3,4-dihydrobenzo[e][1,4]diazepin-5-one

78755-81-4

flumazenil

Conditions
ConditionsYield
Stage #1: (E)-(dimethylamino-methyleneamino)-acetic acid ethyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -35℃; for 1.5h;
Stage #2: 2-chloro-7-fluoro-4-methyl-3,4-dihydrobenzo[e][1,4]diazepin-5-one With Dimethyl-p-toluidine In tetrahydrofuran at -40 - -35℃; for 3h;
Stage #3: With acetic acid In tetrahydrofuran for 6h; pH=5 - 7; Heating;
98%
105-56-6

ethyl 2-cyanoacetate

193693-31-1

2-chloro-7-fluoro-4-methyl-3,4-dihydrobenzo[e][1,4]diazepin-5-one

78755-81-4

flumazenil

Conditions
ConditionsYield
With N,N-dimethyl-aniline; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Reagent/catalyst; Solvent;61.3%
658075-93-5

8-amino-5,6-dihydro-5-methyl-6-oxo-4H-imidazol[1,5-a][1,4]benzodiazepine-3-carboxylic acid ethyl ester

78755-81-4

flumazenil

Conditions
ConditionsYield
With pyridine; hydrogen fluoride; sodium nitrite at 20 - 120℃; for 2.5h;51%
Multi-step reaction with 2 steps
1: BF3*Et2O; t-butyl nitrite / CH2Cl2 / -15 - 5 °C
2: 160 mg / 0.67 h / 130 °C
View Scheme
2999-46-4

Ethyl isocyanoacetate

78755-80-3

7-fluoro-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione

78755-81-4

flumazenil

Conditions
ConditionsYield
Multistep reaction;

(dimethylamino-methyleneamino)-(7-fluoro-4-methyl-5-oxo-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-ylidene)-acetic acid ethyl ester

A

78755-81-4

flumazenil

B

(dimethylamino-methyleneamino)-(7-fluoro-4-methyl-5-oxo-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-ylidene)-acetic acid ethyl ester

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran pH=5; Heating;

C15H14N5O3(1+)*BF4(1-)

78755-81-4

flumazenil

Conditions
ConditionsYield
at 130℃; for 0.666667h; Balz-Schiemann reaction;160 mg
2999-46-4

Ethyl isocyanoacetate

78755-81-4

flumazenil

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.79 g / sodium hydride / dimethylformamide; tetrahydrofuran / 18 h
2: 97 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 2 h
3: BF3*Et2O; t-butyl nitrite / CH2Cl2 / -15 - 5 °C
4: 160 mg / 0.67 h / 130 °C
View Scheme
Multi-step reaction with 3 steps
1: N-methyl-acetamide; water; acetic acid; ethyl acetate
2: potassium carbonate / ethanol; water; trifluoroacetic acid
3: N-methyl-acetamide; water
View Scheme
84377-96-8

7-nitro-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5-(1H)-dione

78755-81-4

flumazenil

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hydride; diethyl chlorophosphate / tetrahydrofuran; dimethylformamide / 0.5 h / 0 °C
2: 1.79 g / sodium hydride / dimethylformamide; tetrahydrofuran / 18 h
3: 97 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 2 h
4: BF3*Et2O; t-butyl nitrite / CH2Cl2 / -15 - 5 °C
5: 160 mg / 0.67 h / 130 °C
View Scheme
84377-97-9

8-nitro-5,6-dihydro-5-methyl-6-oxo-4H-imidazol[1,5-a][1,4]benzodiazepine-3-carboxylic acid ethyl ester

78755-81-4

flumazenil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 97 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 2 h
2: BF3*Et2O; t-butyl nitrite / CH2Cl2 / -15 - 5 °C
3: 160 mg / 0.67 h / 130 °C
View Scheme

2-chloro-4-methyl-7-nitro-3,4-dihydro-benzo[e][1,4]diazepin-5-one

78755-81-4

flumazenil

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.79 g / sodium hydride / dimethylformamide; tetrahydrofuran / 18 h
2: 97 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 2 h
3: BF3*Et2O; t-butyl nitrite / CH2Cl2 / -15 - 5 °C
4: 160 mg / 0.67 h / 130 °C
View Scheme

Flumazenil Specification

Flumazenil, with the CAS NO.78755-81-4, has the IUPAC Name of Ethyl 8-fluoro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate. Synonyms of it are 4H-Imidazo(1,5-a)(1,4)benzodiazepine-3-carboxylic acid, 8-fluoro-5,6-dihydro-5-methyl-6-oxo-, ethyl ester; 4H-Imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid, 8-fluoro-5,6-dihydro-5-methyl-6-oxo-, ethyl ester; 8-Fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid ethyl ester; 8-Fluoro-5-méthyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazépine-3-carboxylate d'éthyle. It is a benzodiazepine receptor antagonist available for injection only, and the only benzodiazepine receptor antagonist on the market today.

Physical properties about Flumazenil are: (1)ACD/LogP: 2.151; (2)ACD/LogD (pH 5.5): 2.15; (3)ACD/LogD (pH 7.4): 2.15; (4)ACD/BCF (pH 5.5): 25.41; (5)ACD/BCF (pH 7.4): 25.41; (6)ACD/KOC (pH 5.5): 352.59; (7)ACD/KOC (pH 7.4): 352.60; (8)#H bond acceptors: 6; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.634 ; (11)Molar Refractivity: 77.586 cm3; (12)Molar Volume: 217.075 cm3; (13)Polarizability: 30.757 10-24cm3; (14)Surface Tension: 48.4690017700195 dyne/cm; (15)Density: 1.397 g/cm3; (16)Flash Point: 273.115 °C; (17)Enthalpy of Vaporization: 80.269 kJ/mol; (18)Boiling Point: 527.983 °C at 760 mmHg

Uses of Flumazenil: Flumazenil is used to against the sedative effect and disorientation after use of overdose of benzodiazepine drugs leather, and has anticonvulsant activity and antiepileptic effect. It can also be used after the recovery period and encephalopathy due to cirrhosis of the liver due to alcoholism, unexplained loss of consciousness diagnostic medicine. Besides it is also used to identify the benzodiazepine class and other drug intoxication or brain damage. It is still used as central nervous system stimulant.

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Take off immediately all contaminated clothing;
3. Wear suitable protective clothing, gloves and eye/face protection;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C15H14FN3O3/c1-3-22-15(21)13-12-7-18(2)14(20)10-6-9(16)4-5-11(10)19(12)8-17-13/h4-6,8H,3,7H2,1-2H3;
(2)InChIKey=OFBIFZUFASYYRE-UHFFFAOYSA-N;
(3)Smilesn12c3c(C(=O)N(Cc1c(nc2)C(=O)OCC)C)cc(cc3)F

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous > 30mg/kg (30mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
dog LDLo oral > 640mg/kg (640mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
man LDLo intravenous 5700ng/kg/C (.0057mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

CARDIAC: CHANGE IN RATE
British Medical Journal. Vol. 304, Pg. 1415, 1992.
mouse LD50 intraperitoneal 4gm/kg (4000mg/kg)   Drugs of the Future. Vol. 7, Pg. 402, 1982.
mouse LD50 intravenous 143mg/kg (143mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: REGIDITY
Journal de Toxicologie Clinique et Experimentale. Vol. 7, Pg. 223, 1987.
mouse LD50 oral 1300mg/kg (1300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: REGIDITY

BEHAVIORAL: TREMOR
Journal de Toxicologie Clinique et Experimentale. Vol. 7, Pg. 223, 1987.
mouse LDLo subcutaneous > 1gm/kg (1000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
rabbit LD50 oral 2gm/kg (2000mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: REGIDITY

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal de Toxicologie Clinique et Experimentale. Vol. 7, Pg. 223, 1987.
rat LD50 intraperitoneal 1360mg/kg (1360mg/kg)   Drugs of the Future. Vol. 7, Pg. 402, 1982.
rat LD50 intravenous 85mg/kg (85mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal de Toxicologie Clinique et Experimentale. Vol. 7, Pg. 223, 1987.
rat LD50 oral 4200mg/kg (4200mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: REGIDITY

BEHAVIORAL: TREMOR
Journal de Toxicologie Clinique et Experimentale. Vol. 7, Pg. 223, 1987.
women TDLo intravenous 4ug/kg (.004mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Pediatric Emergency Care. Vol. 11, Pg. 186, 1995.
women TDLo oral 2mg/kg/2D-I (2mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: AGGRESSION

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Lancet. Vol. 339, Pg. 488, 1992.

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