Nimetazepam

Nimetazepam
Clinical data
Trade names Erimin
AHFS/Drugs.com International Drug Names
Pregnancy
category
  • X
Routes of
administration

Oral

Addiction liability: High
ATC code N05
Legal status
Legal status
Pharmacokinetic data
Bioavailability 95%
Metabolism Hepatic
Biological half-life 14–30 hours
Excretion Renal
Identifiers
CAS Number 2011-67-8 N
PubChem (CID) 4496
DrugBank ? N
ChemSpider 4340 YesY
UNII 4532264KW6 YesY
KEGG D01593 YesY
ChEBI CHEBI:31912 N
ChEMBL CHEMBL13341 YesY
ECHA InfoCard 100.016.302
Chemical and physical data
Formula C16H13N3O3
Molar mass 295.3 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

Nimetazepam (marketed under brand name Erimin) is an intermediate-acting hypnotic drug which is a benzodiazepine derivative. It was first synthesized by a team at Hoffmann-La Roche in 1962.[1] It possesses hypnotic, anxiolytic, sedative, and skeletal muscle relaxant properties. Nimetazepam is also an anticonvulsant.[2] It is sold in 5 mg tablets known as Erimin. It is generally prescribed for the short-term treatment of severe insomnia in patients who have difficulty falling asleep or maintaining sleep. The sole global manufacturer of Nimetazepam (Sumitomo Japan) has ceased manufacturing Erimin since early November 2015. Patients being prescribed Erimin are being switched to other hypnotics, e.g. etizolam, flunitrazepam, etc.

Pharmacokinetics

Taken orally, nimetazepam has very good bioavailability with nearly 100% being absorbed from the gut. It is among the most rapidly absorbed and quickest acting oral benzodiazepines, and hypnotic effects are typically felt within 15–30 minutes after oral ingestion. The blood level decline of the parent drug was biphasic with the short half-life ranging from 0.5–0.7 hours and the terminal half-life from 8 to 26.5 hours (mean 17.25 hours). It is the N-methylated analogue of nitrazepam (Mogadon, Alodorm), to which it is partially metabolized. Nitrazepam has a long elimination half-life, so effects of repeated dosage tend to be cumulative.

Recreational use

Nimetazepam has a particular reputation in the Malay Peninsula for recreational use, at RM 15 per tab, and is particularly popular among persons addicted to amphetamines or opioids.[3][4]

Nimetazepam is currently a Schedule IV drug under the international Convention on Psychotropic Substances of 1971.[5]

In Singapore, nimetazepam is a class A drug under the Misuse of Drugs Act.[6]

In Hong Kong, nimetazepam is regulated under Schedule 1 of Hong Kong's Chapter 134 Dangerous Drugs Ordinance. Nimetazepam can only be used legally by health professionals and for university research purposes. The substance can be given by pharmacists under a prescription. Anyone who supplies the substance without prescription can be fined $10000 (HKD). The penalty for trafficking or manufacturing the substance is a $5,000,000 (HKD) fine and life imprisonment. Possession of the substance for consumption without license from the Department of Health is illegal with a $1,000,000 (HKD) fine and/or 7 years of jail time.[7]

In Victoria Australia, nimetazepam is regulated under Schedule 11 of "Drugs, Poisons and Controlled substances act 1981". It is deemed to fall under the category of "7-NITRO-1,4-BENZODIAZEPINES not included elsewhere in this Part". .[8]

Toxicity

In a rat study Nimetazepam showed greater damage to the fetus, as did nitrazepam when compared against other benzodiazepines, all at a dosage of 100 mg/kg. Diazepam however showed relatively weak fetal toxicities.[9] The same fetotoxicity of nitrazepam could not be observed in mice and is likely due to the particular metabolism of the drug in the rat.[10]

See also

References

  1. ↑ US patent 3109843, Reeder, E. ; Sternbach, L. H., "Process for preparing 5-phenyl-1,2-dihydro-3H-1,4-benzodiazepines", issued 1963-11-05, assigned to Hoffmann-La Roche
  2. ↑ Fukinaga, M.; Ishizawa, K.; Kamei, C. (1998). "Anticonvulsant properties of 1,4-benzodiazepine derivatives in amygdaloid-kindled seizures and their chemical structure-related anticonvulsant action". Pharmacology. 57 (5): 233–241. doi:10.1159/000028247. PMID 9742288.
  3. ↑ Chong, Y. K.; Kaprawi, M. M.; Chan, K. B. (2004). "The Quantitation of Nimetazepam in Erimin-5 Tablets and Powders by Reverse-Phase HPLC". Microgram Journal. 2 (1–4): 27–33.
  4. ↑ Devaney, M.; Reid, G.; Baldwin, S. (2005). "Situational analysis of illicit drug issues and responses in the Asia-Pacific region" (pdf). ANCD Research Paper 12. Canberra: Australian National Council on Drugs.
  5. ↑ "List of psychotropic substances under international control" (pdf). Green List Annex to the annual statistical report on psychotropic substances (form P) (23rd ed.). International Narcotics Control Board. August 2003. Retrieved 2011-12-06.
  6. ↑ "Misuse of drugs act, chapter 185".
  7. ↑ "Bilingual Laws Information System". The Government of the Hong Kong Special Administrative Region of the People's Republic of China.
  8. ↑ "Victorian Legislation and Parliamentary Documents". The State Government Victoria.
  9. ↑ Saito, H.; Kobayashi, H.; Takeno, S.; Sakai, T. (1984). "Fetal toxicity of benzodiazepines in rats". Research communications in chemical pathology and pharmacology. 46 (3): 437–447. PMID 6151222.
  10. ↑ Takeno, S.; Hirano, Y.; Kitamura, A.; Sakai, T. (1993). "Comparative Developmental Toxicity and Metabolism of Nitrazepam in Rats and Mice". Toxicology and Applied Pharmacology. 121 (2): 233–238. doi:10.1006/taap.1993.1150. PMID 8346540.
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