Structure via PubChem · Public domain (PubChem)
nimetazepam
Sign in to saveAlso 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
Research
42 papers- Quantification of nimetazepam and its metabolite in human hair samples using liquid chromatography-tandem mass spectrometry: Case report.Legal medicine (Tokyo, Japan) · 2023
- Determination of nimetazepam and 7-aminonimetazepam in human urine by using liquid chromatography-tandem mass spectrometry.Forensic science international · 2013
- Comparative metabolic study of nimetazepam and its desmethyl derivative (nitrazepam) in rats.Xenobiotica; the fate of foreign compounds in biological systems · 1975
- Vortex-assisted dispersive liquid-liquid microextraction-gas chromatography (VADLLME-GC) determination of residual ketamine, nimetazepam, and xylazine from drug-spiked beverages appearing in liquid, droplet, and dry forms.Journal of forensic sciences · 2022
- Simultaneous quantification of urine flunitrazepam, nimetazepam and nitrazepam by using liquid chromatography tandem mass spectrometry.Clinica chimica acta; international journal of clinical chemistry · 2013
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- 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 sectionsContents
- 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.