| Identification | More | [Name]
Nimetazepam | [CAS]
2011-67-8 | [Synonyms]
1,3-dihydro-1-methyl-7-nitro-5-phenyl-2h-1,4-benzodiazepin-2-one
1-methyl-7-nitro-5-phenyl-1h-1,4-benzodiazepin-2(3h)-one
NIMETAZEPAM
1,3-dihydro-1-methyl-7-nitro-5-phenyl-2h-4-benzodiazepin-2-one
1-Methyl-5-phenyl-7-nitro-1,3-dihydro-2H-1,4-benzodiazepin-2-one
1-Methyl-7-nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
1-Methylnitrazepam
2H-1,4-Benzodiazepin-2-one, 1,3-dihydro-1-methyl-7-nitro-5-phenyl-
Elimin
Hypnon
Nimetazam
Nitrazepam, methylated
ro5-3453
S 1530
N-Methylmogadon | [EINECS(EC#)]
217-931-5 | [Molecular Formula]
C16H13N3O3 | [MDL Number]
MFCD00242916 | [Molecular Weight]
295.29 | [MOL File]
2011-67-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
156.5-157.5° | [Boiling point ]
436.98°C (rough estimate) | [density ]
1.1952 (rough estimate) | [refractive index ]
1.6500 (estimate) | [Fp ]
9℃ | [storage temp. ]
-20°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
pKa 2.53(EtOH/H2O,t =25,Iundefined) (Uncertain) | [color ]
Light Yellow to Dark Yellow | [CAS DataBase Reference]
2011-67-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Nimetazepam(2011-67-8) |
| Safety Data | Back Directory | [Hazard Codes ]
F,T | [Risk Statements ]
11-23/24/25-39/23/24/25 | [Safety Statements ]
16-36/37-45 | [RIDADR ]
UN1230 - class 3 - PG 2 - Methanol, solution | [WGK Germany ]
1 | [Toxicity]
LD50 in male, female mice, rats (mg/kg): 910, 750, 1150, 970 orally; 970, 840, 970, 980 i.p.; 1500, 1500, 1000, 1000 s.c. (Sakai) | [DEA Controlled Substances]
CSCN: 2837
CSA SCH: Schedule IV
NARC: No |
| Hazard Information | Back Directory | [Chemical Properties]
Dark yellow Solid | [Originator]
Erimin,Sumitomo,Japan,1977 | [Uses]
Sedative, hypnotic.
Controlled substance. | [Definition]
ChEBI: A nitrazepam which is substituted at positions 1 by a methyl groups. It is used as an anticonvulsant and as a hypnotic for the short-term management of insomnia. | [Manufacturing Process]
To a suspension of 73.9 g of 1-methyl-5-nitro-3-phenylindole-2-carbonitrile in
1.5 liters of dry tetrahydrofuran is added dropwise a solution of 126 g of
boron trifluoride etherate in 220 ml of dry tetrahydrofuran with stirring for 2
hours. After addition, stirring is continued for an additional 3 hours. To the reaction mixture is added dropwise 370 ml of water and then 370 ml of
concentrated hydrochloric acid with stirring under ice-cooling.
The resulting precipitate is collected by filtration, washed with water followed
by ethanol, and dried to give 56.3 g of crude 2-aminomethyl-1-methyl-5-
nitro-3-phenylindole hydrochloride, melting point 263°C to 267°C.
To a suspension of 6.5 g of 2-aminomethyl-1-methyl-5-nitro-3-phenylindole in
65 ml of glacial acetic acid is added dropwise a solution of 6.5 g of chromic
anhydride in 6.5 ml of water at 20°C with stirring. The mixture is stirred at
room temperature overnight and thereto is added 195 ml of water. To the
mixture is added dropwise 100 ml of 28% ammonia water with stirring under
cooling. The resultant precipitate is collected by filtration, washed with water
and dried to give 5.9 g of a crude product having melting point 135°C to
140°C. Fractional recrystallization from ethanol gives 3.8 g of 1-methyl-7-
nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepine-2-one as yellow plates,
melting point 153°C to 156°C. Further recrystallization from the same solvent
gives pale yellow plates having melting point 156°C to 156.5°C. | [Therapeutic Function]
Tranquilizer |
|