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nimetazepam

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nimetazepam

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Also known as 1-methyl-7-nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one, 1,3-dihydro-1-methyl-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one, 1-methyl-5-phenyl-7-nitro-1,3-dihydro-2H-1,4-benzodiazepin-2-one, Ro 5-3453, methylnitrazepam, 1-methylnitrazepam

Nimetazepam (marketed under brand name Erimin and Lavol) is an intermediate-acting hypnotic drug which is a benzodiazepine derivative. It was first synthesized by a team at Hoffmann-La Roche in 1964. It possesses powerful hypnotic, anxiolytic, sedative, and skeletal muscle relaxant properties. Nimetazepam is also a particularly potent anticonvulsant. It is marketed in 5 mg tablets known as Erimin, which is the brand name manufactured and marketed by the large Japanese corporation Sumitomo. Japan is the sole manufacturer of nimetazepam in the world. Outside of Japan, Erimin is available in

Chemical data

Formula
C16H13N3O3
Molecular weight
295.29 g/mol
IUPAC name
1-methyl-7-nitro-5-phenyl-3H-1,4-benzodiazepin-2-one
SMILES
CN1C(=O)CN=C(C2=C1C=CC(=C2)[N+](=O)[O-])C3=CC=CC=C3
InChIKey
GWUSZQUVEVMBPI-UHFFFAOYSA-N
XLogP
2.2
Polar surface area
78.5 Ų
H-bond donors
0
H-bond acceptors
4
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Phase 2
Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Mass
295.096
Show 5 more facts
Commons category
Nimetazepam
chemical formula
C₁₆H₁₃N₃O₃
canonical SMILES
CN1C(=O)CN=C(C2=C1C=CC(=C2)[N+](=O)[O-])C3=CC=CC=C3
World Health Organisation international non-proprietary name
nimetazepam
MCN code
2933.91.61
Sources (2)

via Wikidata · CC0

~8 min read

Encyclopedic overview

7 sections
Contents
  • Pharmacokinetics
  • Recreational use
  • Drug misuse
  • Legal status
  • Toxicity
  • See also
  • References

Nimetazepam (marketed under brand name Erimin and Lavol) is an intermediate-acting hypnotic drug which is a benzodiazepine derivative. It was first synthesized by a team at Hoffmann-La Roche in 1964. It possesses powerful hypnotic, anxiolytic, sedative, and skeletal muscle relaxant properties. Nimetazepam is also a particularly potent anticonvulsant. It is marketed in 5 mg tablets known as Erimin, which is the brand name manufactured and marketed by the large Japanese corporation Sumitomo. Japan is the sole manufacturer of nimetazepam in the world. Outside of Japan, Erimin is available in much of East and Southeast Asia and was widely prescribed for the short-term treatment of severe insomnia in patients who have difficulty falling asleep or maintaining sleep. Sumitomo has ceased manufacturing Erimin since November 2015. It is still available as a generic drug or as Lavol.

Nimetazepam was widely prescribed in the 1980s and 1990s, particularly in Japan, Malaysia, Brunei, the Philippines, Thailand, Indonesia, Hong Kong and Singapore. Prescriptions for the drug have decreased dramatically since 2005 due to rampant misuse and addiction. It is primarily used as an anticonvulsant in children. It is also still used in the most severe and debilitating cases of insomnia in an inpatient setting or in short term outpatient treatment. Hypnotic benzodiazepines estazolam and nitrazepam are used more frequently than nimetazepam for this purpose. Antidepressants such as trazodone and mirtazapine or Z-drugs like zopiclone and zolpidem are first line treatment for insomnia.

Excerpted from Wikipedia’s “nimetazepam” article, available under the CC BY-SA 4.0 licence.