| | Nimetazepam Basic information |
| Product Name: | Nimetazepam | | Synonyms: | 1-methyl-7-nitro-5-phenyl-1h-1,4-benzodiazepin-2(3h)-one;N-Methylmogadon;1-methyl-7-nitro-5-phenyl-3H-1,4-benzodiazepin-2-one;1,3-dihydro-1-methyl-7-nitro-5-phenyl-2h-1,4-benzodiazepin-2-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 | | CAS: | 2011-67-8 | | MF: | C16H13N3O3 | | MW: | 295.29 | | EINECS: | 217-931-5 | | Product Categories: | Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 2011-67-8.mol |  |
| | Nimetazepam Chemical Properties |
| 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) |
| 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 |
| | Nimetazepam Usage And Synthesis |
| 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 |
| | Nimetazepam Preparation Products And Raw materials |
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