Nimetazepam

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 Structure
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)
pkapKa 2.53(EtOH/H2O,t =25,Iundefined) (Uncertain)
form Solid
color Light Yellow to Dark Yellow
CAS DataBase Reference2011-67-8(CAS DataBase Reference)
NIST Chemistry ReferenceNimetazepam(2011-67-8)
Safety Information
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
ToxicityLD50 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 SubstancesCSCN: 2837
CSA SCH: Schedule IV
NARC: No
MSDS Information
Nimetazepam Usage And Synthesis
Chemical PropertiesDark yellow Solid
OriginatorErimin,Sumitomo,Japan,1977
UsesSedative, hypnotic. Controlled substance.
DefinitionChEBI: 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 ProcessTo 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 FunctionTranquilizer
Nimetazepam Preparation Products And Raw materials
Raw materialsHydrochloric acid-->Boron trifluoride diethyl etherate-->Chromium(VI) oxide
Motrazepam 3-hydroxyflunitrazepam [N-METHYL-3H]FLUNITRAZEPAM Clonazepam FLUNITRAZEPAM-(N-METHYL-D3) FLUNITRAZEPAM, [METHYL-3H] FLUNITRAZEPAM Nimetazepam Kresoxim-methyl DBU PHENYL VALERATE Thiophanate-methyl Trimethylphenylammonium chloride Pyrrolo(3,2,1-jk)(1,4)benzodiazepin-4(3H)-one, 6,7-dihydro-9-nitro-1-p henyl- Methyl acetate Methyl bromide 1-(2,6-Dimethylphenoxy)-2-propanamine METHYL CLONAZEPAM

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