词条 | Flunitrazepam |
释义 |
|Watchedfields = changed |verifiedrevid = 477167367 |IUPAC_name = 5-(2-fluorophenyl)-1-methyl-7-nitro-1H-benzo[e][1,4]diazepin-2(3H)-one |image = Flunitrazepam structure.svg |width = 222 |image2 = Flunitrazepam-from-xtal-3D-balls.png |pronounce = {{IPAc-en|ˌ|f|l|uː|n|ᵻ|ˈ|t|r|æ|z|ᵻ|p|æ|m}} |tradename = Rohypnol |pregnancy_AU = C |legal_AU = S8 |legal_CA = Schedule I |legal_DE = Anlage III |legal_UK = Class C |legal_US = Schedule IV Sweden schedule II |legal_UN = Psychotropic Schedule III |dependency_liability = Very high |routes_of_administration = By mouth (tablets) |bioavailability = 64–77% (by mouth) 50% (suppository) |metabolism = Liver |elimination_half-life = 18–26 hours |excretion = Kidney |IUPHAR_ligand = 4193 |CAS_number_Ref = {{cascite|correct|??}} |CAS_number = 1622-62-4 |ATC_prefix = N05 |ATC_suffix = CD03 |PubChem = 3380 |DrugBank_Ref = {{drugbankcite|correct|drugbank}} |DrugBank = DB01544 |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID = 3263 |UNII_Ref = {{fdacite|correct|FDA}} |UNII = 620X0222FQ |KEGG_Ref = {{keggcite|correct|kegg}} |KEGG = D01230 |ChEMBL_Ref = {{ebicite|correct|EBI}} |ChEMBL = 13280 |C=16 |H=12 |F=1 |N=3 |O=3 |molecular_weight = 313.3 g/mol |smiles = [O-][N+](C1=CC2=C(C=C1)N(C)C(CN=C2C3=CC=CC=C3F)=O)=O |StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChI = 1S/C16H12FN3O3/c1-19-14-7-6-10(20(22)23)8-12(14)16(18-9-15(19)21)11-4-2-3-5-13(11)17/h2-8H,9H2,1H3 |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey = PPTYJKAXVCCBDU-UHFFFAOYSA-N }}Flunitrazepam, also known as Rohypnol among other names,[1] is an intermediate acting benzodiazepine used in some countries to treat severe insomnia and in fewer, early in anesthesia.[1] As with other hypnotics, flunitrazepam has been advised to be prescribed only on a short-term basis or by those with chronic insomnia on an occasional basis.[1] It was patented in 1962 and came into medical use in 1974.[2] Flunitrazepam has been referred to as a date rape drug, though the percentage of reported rape cases in which it is involved is small.[3] {{TOC limit}}UseIn countries where the drug is used, it is used for treatment of sleeping problems, and in some countries to begin anesthesia.[1][7] These were also the uses for which it was originally studied.[4] Adverse effectsAdverse effects of flunitrazepam include dependence, both physical and psychological; reduced sleep quality resulting in somnolence; and overdose, resulting in excessive sedation, impairment of balance and speech, respiratory depression or coma, and possibly death. Because of the latter, flunitrazepam is commonly used in suicide. When used in pregnancy, it might cause hypotonia. DependenceFlunitrazepam as with other benzodiazepines can lead to drug dependence and benzodiazepine withdrawal syndrome.[9] Discontinuation may result in the appearance of withdrawal symptoms. Abrupt withdrawal may lead to a benzodiazepine withdrawal syndrome characterised by seizures, psychosis, insomnia, and anxiety. Rebound insomnia, worse than baseline insomnia, typically occurs after discontinuation of flunitrazepam even after short-term single nightly dose therapy.[5] Sleep depth{{medical citations needed|section|date=October 2017}}Flunitrazepam produces a decrease in delta wave activity. The effect of benzodiazepine drugs on delta waves, however, may not be mediated via benzodiazepine receptors. Delta activity is an indicator of depth of sleep within non-REM sleep; increased levels of delta sleep reflects better quality of sleep. Thus, flunitrazepam and other benzodiazepines{{Citation needed|date=January 2017}} cause a deterioration in sleep quality. Cyproheptadine may be superior{{Citation needed|date=May 2018}} to benzodiazepines in the treatment of insomnia as it enhances sleep quality based on EEG studies. Paradoxical effectsFlunitrazepam may cause a paradoxical reaction in some individuals causing symptoms including anxiety, aggressiveness, agitation, confusion, disinhibition, loss of impulse control, talkativeness, violent behavior, and even convulsions. Paradoxical adverse effects may even lead to criminal behaviour.[6] Hypotonia{{See also|Hypotonia}}Benzodiazepines such as flunitrazepam are lipophilic and rapidly penetrate membranes and, therefore, rapidly cross over into the placenta with significant uptake of the drug. Use of benzodiazepines including flunitrazepam in late pregnancy, especially high doses, may result in hypotonia, also known as floppy baby syndrome.[7] OtherFlunitrazepam impairs cognitive functions. This may appear as lack of concentration, confusion and anterograde amnesia. It can be described as a hangover-like effect which can persist to the next day.[8] It also impairs psychomotor functions similar to other benzodiazepines and nonbenzodiazepine hypnotic drugs; falls and hip fractures were frequently reported. The combination with alcohol increases these impairments. Partial, but incomplete tolerance develops to these impairments.[9] Other adverse effects include:
Special precautionsBenzodiazepines require special precaution if used in the elderly, during pregnancy, in children, in alcohol- or drug-dependent individuals, and in individuals with comorbid psychiatric disorders.[10] Impairment of driving skills with a resultant increased risk of road traffic accidents is probably the most important adverse effect. This side-effect is not unique to flunitrazepam but also occurs with other hypnotic drugs. Flunitrazepam seems to have a particularly high risk of road traffic accidents compared to other hypnotic drugs. Extreme caution should be exercised by drivers after taking flunitrazepam.[11][12] InteractionsThe use of flunitrazepam in combination with alcoholic beverages synergizes the adverse effects, and can lead to toxicity and death.[3] Overdose{{See also|Benzodiazepine overdose}}Flunitrazepam is a drug that is frequently involved in drug intoxication, including overdose.[13][14] Overdose of flunitrazepam may result in excessive sedation, or impairment of balance or speech. This may progress in severe overdoses to respiratory depression or coma and possibly death. The risk of overdose is increased if flunitrazepam is taken in combination with CNS depressants such as ethanol (alcohol) and opioids. Flunitrazepam overdose responds to the benzodiazepine receptor antagonist flumazenil, which thus can be used as a treatment. DetectionAs of 2016, blood tests can identify flunitrazepam at concentrations of as low as 4 ng/ml; the elimination half life of the drug is 11–25 hours. For urine samples, metabolites can be identified 60 hours to 28 days, depending on the dose and analytical method used. Hair and saliva can also be analyzed; hair is useful when a long time has transpired since ingestion, and saliva for workplace drug tests.[21] Flunitrazepam can be measured in blood or plasma to confirm a diagnosis of poisoning in hospitalized patients, provide evidence in an impaired driving arrest, or assist in a medicolegal death investigation. Blood or plasma flunitrazepam concentrations are usually in a range of 5–20 μg/L in persons receiving the drug therapeutically as a nighttime hypnotic, 10–50 μg/L in those arrested for impaired driving and 100–1000 μg/L in victims of acute fatal overdosage. Urine is often the preferred specimen for routine drug abuse monitoring purposes. The presence of 7-aminoflunitrazepam, a pharmacologically-active metabolite and in vitro degradation product, is useful for confirmation of flunitrazepam ingestion. In postmortem specimens, the parent drug may have been entirely degraded over time to 7-aminoflunitrazepam.[15][16][17] Other metabolites include desmethylflunitrazepam and 3-hydroxydesmethylflunitrazepam. PharmacologyThe main pharmacological effects of flunitrazepam are the enhancement of GABA at various GABA receptors.[3] While 80% of flunitrazepam that is taken orally is absorbed, bioavailability in suppository form is closer to 50%.[18] Flunitrazepam has a long half-life of 18–26 hours, which means that flunitrazepam's effects after nighttime administration persist throughout the next day.[8] Flunitrazepam is lipophilic and is metabolised hepatically via oxidative pathways. The enzyme CYP3A4 is the main enzyme in its phase 1 metabolism in human liver microsomes.[19] ChemistryFlunitrazepam is classed as a nitro-benzodiazepine. It is the fluorinated N-methyl derivative of nitrazepam. Other nitro-benzodiazepines include nitrazepam (the parent compound), nimetazepam (methylamino derivative) and clonazepam (2ʹ-chlorinated derivative).[20] HistoryFlunitrazepam was discovered at Roche as part of the benzodiazepine work led by Leo Sternbach; the patent application was filed in 1962 and it was first marketed in 1974.[21][22] Due to abuse of the drug for date rape and recreation, in 1998 Roche modified the formulation to give lower doses, make it less soluble, and add a blue dye for easier detection in drinks.[23] It was never marketed in the US, and by 2016 had been withdrawn from the markets in Spain, France, Germany, and the UK.[23] Society and cultureRecreational and illegal usesRecreational useA 1989 article in the European Journal of Clinical Pharmacology reports that benzodiazepines accounted for 52% of prescription forgeries, suggesting that benzodiazepines was a major prescription drug class of abuse. Nitrazepam accounted for 13% of forged prescriptions.[24] Flunitrazepam and other sedative hypnotic drugs are detected frequently in cases of people suspected of driving under the influence of drugs. Other benzodiazepines and nonbenzodiazepines (anxiolytic or hypnotic) such as zolpidem and zopiclone (as well as cyclopyrrolones, imidazopyridines, and pyrazolopyrimidines) are also found in high numbers of suspected drugged drivers. Many drivers have blood levels far exceeding the therapeutic dose range, suggesting a high degree of abuse potential for benzodiazepines and similar drugs.[25] SuicideIn studies in Sweden, flunitrazepam was the second most common drug used in suicides, being found in about 16% of cases.[26] In a retrospective Swedish study of 1587 deaths, in 159 cases benzodiazepines were found. In suicides when benzodiazepines were implicated, the benzodiazepines flunitrazepam and nitrazepam were occurring in significantly higher concentrations, compared to natural deaths. In 4 of the 159 cases, where benzodiazepines were found, benzodiazepines alone were the only cause of death. It was concluded that flunitrazepam and nitrazepam might be more toxic than other benzodiazepines.[27][28] Drug-facilitated sexual assault{{Main|Drug facilitated sexual assault}}Flunitrazepam is known to induce anterograde amnesia in sufficient doses; individuals are unable to remember certain events that they experienced while under the influence of the drug, which complicates investigations.[29][30] This effect could be particularly dangerous if flunitrazepam is used to aid in the commission of sexual assault; victims may be unable to clearly recall the assault, the assailant, or the events surrounding the assault.[23] While use of flunitrazepam in sexual assault has been prominent in the media, as of 2015 appears to be fairly rare, and use of alcohol and other benzodiazepine drugs in date rape appears to be a larger but underreported problem.[3] Drug-facilitated robberyIn the United Kingdom, the use of flunitrazepam and other "date rape" drugs have also been connected to stealing from sedated victims. An activist quoted by a British newspaper estimated that up to 2,000 individuals are robbed each year after being spiked with powerful sedatives,[31] making drug-assisted robbery a more commonly reported problem than drug-assisted rape. Regional useFlunitrazepam is a Schedule III drug under the international Convention on Psychotropic Substances of 1971.[32]
NamesFlunitrazepam is marketed under many brand names in the countries where it is legal.[43] It also has many street names, including "roofie" and "ruffie".[42] References1. ^1 2 3 {{cite web|url=http://www.health.nsw.gov.au/pharmaceutical/Documents/guide-flunitraz-alpraz.pdf|format=PDF|title=Prescribing of Benzodiazepines Alprazolam and Flunitrazepam|work=Pharmaceutical Services Branch|publisher=New South Wales Health|date=November 2013}} 2. ^{{cite book |last1=Fischer |first1=Jnos |last2=Ganellin |first2=C. Robin |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=53X |url=https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA53X |language=en}} 3. ^1 2 3 European Monitoring Centre for Drugs and Drug Addiction Benzodiazepines drug profile. Page last updated January 8, 2015 4. ^{{cite journal |last1=Mattila |first1=MA |last2=Larni |first2=HM |title=Flunitrazepam: a review of its pharmacological properties and therapeutic use. |journal=Drugs |date=November 1980 |volume=20 |issue=5 |pages=353-74 |pmid=6108205}} 5. ^{{cite journal |author = Kales A |author2=Scharf MB |author3=Kales JD |author4=Soldatos CR |date = April 20, 1979 |title = Rebound insomnia. 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A study shows interacting factors in fatal cases |journal = Läkartidningen |volume = 90 |issue = 45 |pages = 3954–7 |pmid = 8231567 }} 28. ^{{cite journal |vauthors=Drummer OH, Syrjanen ML, Cordner SM |title=Deaths involving the benzodiazepine flunitrazepam. |journal=The American Journal of Forensic Medicine and Pathology |volume=14 |issue=3 |pages=238–243 |date=September 1993 |pmid=8311057 |doi=10.1097/00000433-199309000-00012}} 29. ^{{cite news|url=http://drugnews.nu/article.asp?id=199|title=Bankrånare stärkte sig med Rohypnol?|publisher=DrugNews}} 30. ^{{cite news|url=http://www.expressen.se/index.jsp?d=737&a=116288|title=Mijailovic var påverkad av våldsdrog|publisher=Expressen}} 31. ^{{cite news| url=https://www.theguardian.com/crime/article/0,2763,1376956,00.html |work=The Guardian |location=London |title='Rape drug' used to rob thousands |first=Tony |last=Thompson |date=December 19, 2004 |accessdate=May 2, 2010}} 32. ^International Narcotics Control Board List of Psychotropic Substances under International Control Green List 26th edition, 2015 33. ^{{cite web| date= August 13, 2004| url= http://www.health.wa.gov.au/notifications/authorisations/drugs/flunitrazepam.cfm| title= Authorisation to Supply or Prescribe Drugs of Addiction: Flunitrazepam| work= Statutory Medical Notifications| publisher= Department of Health, Government of Western Australia| accessdate= 2006-03-13| archiveurl = https://web.archive.org/web/20060828184311/http://www.health.wa.gov.au/notifications/authorisations/drugs/flunitrazepam.cfm |archivedate = August 28, 2006}} 34. ^[https://www.gelbe-liste.de/wirkstoffe/flunitrazepam_2624] 35. ^Irish Statute Book, Statutory Instruments, S.I. No. 342/1993 — Misuse of Drugs (Amendment) Regulations, 1993 36. ^1 {{cite web |url=http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=1051 |title=Kusuri-no-Shiori Drug Information Sheet |date=October 2015 |publisher=RAD-AR Council, Japan |accessdate=2016-06-13}} 37. ^{{cite journal |author=Bramness JG |author2=Skurtveit S |author3=Furu K |author4=Engeland A |author5=Sakshaug S |author6=Rønning M. |title=[Changes in the sale and use of flunitrazepam in Norway after 1999] |journal=Tidsskr nor Laegeforen |volume=126 |issue=5 |pages=589–90 |date= February 23, 2006 |pmid=16505866 }} 38. ^{{cite web| date= October 11, 2006| url= http://www.drugaware.co.za/rohypnol.html| title= Drug Wars – About Drugs}} 39. ^http://www.fass.se/LIF/produktfakta/substance_products.jsp?substanceId=IDE4POCOU9OKGVERT1 40. ^[https://www.gov.uk/government/publications/controlled-drugs-list--2/list-of-most-commonly-encountered-drugs-currently-controlled-under-the-misuse-of-drugs-legislation List of most commonly encountered drugs currently controlled under the misuse of drugs legislation] Published 26 May 2016 41. ^DEA [Lists of Scheduling Actions Controlled Substances Regulated Chemicals May 2016] 42. ^1 2 Center for Substance Abuse Research at the University of Maryland Flunitrazepam (Rohypnol) Last Updated on Tuesday, October 29, 2013 43. ^1 Drugs.com [https://www.drugs.com/international/flunitrazepam.html International brands for Flunitrazepam] Page accessed April 13, 2016 External links{{Commons category|Flunitrazepam}}
8 : GABAA receptor positive allosteric modulators|Glycine receptor antagonists|Hoffmann-La Roche|Lactams|Nitrobenzodiazepines|Fluoroarenes|Drug culture|Rape |
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