Nimetazepam
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| Systematic (IUPAC) name | |
| 2-methyl-9-nitro-6-phenyl- 2,5-diazabicyclo[5.4.0]undeca-5,8,10,12-tetraen-3-one |
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| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
| Pregnancy cat. | X |
| Legal status | Prohibited (S9) (AU) Schedule IV (US) IV (International) |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | 95% |
| Metabolism | Hepatic |
| Half-life | 14-30 hours |
| Excretion | Renal |
| Identifiers | |
| CAS number | 2011-67-8  |
| ATC code | N05 |
| PubChem | CID 4496 |
| DrugBank | ? |
| ChemSpider | 4340  |
| UNII | 4532264KW6 |
| KEGG | D01593 |
| ChEMBL | CHEMBL13341 |
| Chemical data | |
| Formula | C16H13N3O3 |
| Mol. mass | 295.3 |
| SMILES | eMolecules & PubChem |
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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 treatment of short-term severe insomnia in patients who have difficulty falling asleep or maintaining sleep.
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[edit] 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 8–26.5 hours (mean 17.25 hours).[citation needed] It is the N-methylated analogue of nitrazepam (Mogadon, Alodorm), to which it is partially metabolised. Nitrazepam has a long elimination half-life, so effects of repeated dosage tend to be cumulative.
[edit] Recreational use
Nimetazepam has a reputation in Malaysia for being particularly subject to abuse especially by persons addicted to amphetamines or opiates.[3][4]
[edit] Legal status
Nimetazepam is currently a Schedule IV drug under the international Convention on Psychotropic Substances of 1971.[5]
In Singapore, nimetazepam is a class C 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]
[edit] 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 100mg/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]
[edit] See also
[edit] References
- ^ 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
- ^ 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.
- ^ 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. http://www.justice.gov/dea/programs/forensicsci/microgram/journal2004/page27.html.
- ^ 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. http://www.ancd.org.au/images/PDF/Researchpapers/rp12_asia_pacific.pdf?phpMyAdmin=rGQ2XkOOsKjMp24r2sFwuVc5ibb.
- ^ "List of psychotropic substances under international control" (pdf). Green List Annex to the annual statistical report on psychotropic substances (form P). International Narcotics Control Board. August 2003. http://www.incb.org/pdf/e/list/green.pdf. Retrieved 2011-12-06.
- ^ "Misuse of drugs act, chapter 185". http://statutes.agc.gov.sg/non_version/cgi-bin/cgi_retrieve.pl?actno=REVED-185.
- ^ "Bilingual Laws Information System". The Government of the Hong Kong Special Administrative Region of the People's Republic of China. http://www.legislation.gov.hk/eng/index.htm.
- ^ "Victorian Legislation and Parliamentary Documents". The State Government Victoria. http://www.legislation.vic.gov.au/domino/Web_Notes/LDMS/PubLawToday.nsf/imgPDF.
- ^ 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.
- ^ 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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