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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 short-term treatment of severe insomnia in patients who have difficulty falling asleep or maintaining sleep.

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.

Recreational use

Nimetazepam has a reputation in Malaysia especially Kuala Perlis for being particularly subject to recreational use especially by persons addicted to amphetamines or opioids.^[3]^[4]

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]

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]

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. edit
^ 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.
^ 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.
^ "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.
^ "Misuse of drugs act, chapter 185".
^ "Bilingual Laws Information System". The Government of the Hong Kong Special Administrative Region of the People's Republic of China.
^ "Victorian Legislation and Parliamentary Documents". The State Government Victoria.
^ 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. edit
^ 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. edit

English Journal

PMID 23085494

Determination of nimetazepam and 7-aminonimetazepam in human urine by using liquid chromatography-tandem mass spectrometry.

Wang KC1, Cheng MC, Hsieh CL, Hsu JF, Wu JD, Lee CK.Author information 1School of Pharmacy, Taipei Medical University, 250 Wu-Hsing Street, Taipei 110, Taiwan, ROC.AbstractWe report determination of metabolites of popular drugs of abuse, including nimetazepam and nitrazepam, in urine by using liquid chromatography/mass spectrometry. Nimetazepam and its metabolites, 7-aminonimetazepam and nitrazepam, were extracted by solid-phase extraction using a DAU cartridge. An ammonium acetate buffer solution (pH 4) and a Luna polar-RP column were selected as the mobile and stationary phase, respectively, for liquid chromatography. Mass spectrometry was used for analysis and was optimized for operation in the positive mode for all analytes. The urine specimens were screened for the presence of nimetazepam and its metabolites nitrazepam and 7-aminonimetazepam at a concentration of 0.1ng/mL. Presence of 7-aminonimetazepam in the urine was an indicator of the subject being a probable abuser of nimetazepam.
Forensic science international.Forensic Sci Int.2013 Jan 10;224(1-3):84-9. doi: 10.1016/j.forsciint.2012.11.001. Epub 2012 Dec 12.
We report determination of metabolites of popular drugs of abuse, including nimetazepam and nitrazepam, in urine by using liquid chromatography/mass spectrometry. Nimetazepam and its metabolites, 7-aminonimetazepam and nitrazepam, were extracted by solid-phase extraction using a DAU cartridge. An am
PMID 23245766

Muscle relaxants for pain management in rheumatoid arthritis.

Richards BL1, Whittle SL, Buchbinder R.Author information 1Institute of Rheumatology and Orthopedics, Royal Prince Alfred Hospital, Camperdown, Australia.brichard@med.usyd.edu.au.AbstractBACKGROUND: Pain management is a high priority for patients with rheumatoid arthritis (RA). Muscle relaxants include drugs that reduce muscle spasm (for example benzodiazepines such as diazepam (Valium), alprazolam (Xanax), lorazepam (Ativan) and non-benzodiazepines such as metaxalone (Skelaxin) or a combination of paracetamol and orphenadrine (Muscol)) and drugs that prevent increased muscle tone (baclofen and dantrolene). Despite a paucity of evidence supporting their use, antispasmodic and antispasticity muscle relaxants have gained widespread clinical acceptance as adjuvants in the management of patients with chronic musculoskeletal pain.
The Cochrane database of systematic reviews.Cochrane Database Syst Rev.2012 Jan 18;1:CD008922. doi: 10.1002/14651858.CD008922.pub2.
BACKGROUND: Pain management is a high priority for patients with rheumatoid arthritis (RA). Muscle relaxants include drugs that reduce muscle spasm (for example benzodiazepines such as diazepam (Valium), alprazolam (Xanax), lorazepam (Ativan) and non-benzodiazepines such as metaxalone (Skelaxin) or
PMID 22258993

Japanese Journal

分散液液マイクロ抽出/ガスクロマトグラフィー/質量分析法による向精神薬の定量

分析化学 = Japan analyst 58(8), 661-665, 2009-08-05
NAID 10025979820

直浸固相ミクロ抽出/ガスクロマトグラフィーによる尿中ベンゾジアゼピン系薬剤の検出

1997-01-31
NAID 120005314025

The Solid Dispersion of Benzodiazepins with Phosphatidylcholine. The Effect of Substituents of Benzodiazepins on the Formation of Solid Dispersions

Chemical & pharmaceutical bulletin 39(11), 3013-3017, 1991-11-25
NAID 110003629007

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リンク元

「ニメタゼパム」

Nimetazepam
Systematic (IUPAC) name
	2-methyl-9-nitro-6-phenyl-; 2,5-diazabicyclo[5.4.0]undeca-5,8,10,12-tetraen-3-one
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy; category	X;
Legal status	AU: Prohibited (S9); US: Schedule IV; UN: Psychotropic Schedule IV;
Routes of; administration	Oral
Pharmacokinetic data
Bioavailability	95%
Metabolism	Hepatic
Biological half-life	14-30 hours
Excretion	Renal
Identifiers
CAS Registry Number	2011-67-8
ATC code	N05
PubChem	CID: 4496
DrugBank	?
ChemSpider	4340
UNII	4532264KW6
KEGG	D01593
ChEBI	CHEBI:31912
ChEMBL	CHEMBL13341
Chemical data
Formula	C16H13N3O3
Molecular mass	295.3
	SMILES [O-][N+](C1=CC2=C(C=C1)N(C)C(CN=C2C3=CC=CC=C3)=O)=O ;
	InChI InChI=1S/C16H13N3O3/c1-18-14-8-7-12(19(21)22)9-13(14)16(17-10-15(18)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3 ; Key:GWUSZQUVEVMBPI-UHFFFAOYSA-N ;
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英: nimetazepam
商: エリミン

[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. edit

[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. edit

[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. edit

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nimetazepam