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Nimetazepam

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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
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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)
Flash point:
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)
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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
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
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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

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