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Flunitrazepam

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Flunitrazepam chemical structure
Flunitrazepam

6-(2-fluorophenyl)-2-methyl-9-nitro-
2,5-diazabicyclo[5.4.0]undeca-
5,8,10,12-tetraen-3-one

IUPAC name
CAS number
1622-62-4
ATC code

N05CD03

PubChem
3380
DrugBank
none
Chemical formula {{{chemical_formula}}}
Molecular weight 313.3
Bioavailability 50%
Metabolism Hepatic
Elimination half-life 18-26 hours
Excretion Renal
Pregnancy category  ?
Legal status Class A in Norway
Routes of administration Oral


Flunitrazepam (formerly marketed under the trade name Rohypnol in North America, IPA: [ˌfluːnaɪˈtræzəpæm]) is a powerful hypnotic drug that is a benzodiazepine derivative. It has powerful hypnotic, sedative, anxiolytic, and skeletal muscle relaxant properties. The drug is sometimes used as a date rape drug (commonly referred to in street slang as a "roofie".)

HistoryEdit

Flunitrazepam was first synthesized in the early 1970s by Roche and was used in hospitals when deep sedation was needed. It first entered the commercial market in Europe, in 1975 and in the 1980s it began to be available in other countries. It first appeared in the U.S. in the early 1990s.

It originally came in 1 mg, 2 mg, and 5 mg doses, but due to its potency and potential for abuse the higher doses were soon taken off the market and it is now only available in 1 mg.

PharmacologyEdit

Like other benzodiazepines, flunitrazepam's pharmacological effects include sedation, muscle relaxation, reduction in anxiety, and prevention of convulsions. However, flunitrazepam's effects are approximately 7 to 10 times more potent than diazepam. The effects of flunitrazepam appear approximately 15 to 20 minutes after oral administration, and last for approximately four to six hours. Some residual effects can persist up to 12 hours or more after administration. While 80% of flunitrazepam that is taken orally is absorbed, bioavailability in suppository form is closer to 50%.[1]

Medical usesEdit

  • In the United States, the drug has not been approved by the Food and Drug Administration for medical use, and is considered to be an illegal drug[2][3][4].
  • In the United Kingdom, the drug is available only by private prescription [5]. Though Rohypnol was discontinued in 1986, Rohypnol use is still present in modern culture; among other uses, it is used in some hospitals to sedate patients undergoing colonoscopy.
  • In Australia, prescription is restricted as a Schedule 8 medicine [6][7]. It is used primarily for the treatment of severe insomnia that has not responded to other treatments. In some states, it is also manufactured in generic form by Alphapharm under the name Hypnodorm. As a Schedule 8 medicine, it is illegal to have this drug in possession without an authority prescription from a registered doctor.
  • In South Africa, Rohypnol is classified as a schedule 6 drug.[8] It is available by prescription only, and restricted to 1 mg doses. Travelers from South Africa to the United States are limited to a 30-day supply. The drug must be declared to US Customs upon arrival. If a valid prescription cannot be produced, the drug may be subject to Customs search and seizure, and the traveler may face criminal charges or deportation.
  • In Norway, the brand Rohypnol has been withdrawn from market because of its reputation, but the drug is still available under the brand-name Flunipam.
  • In Sweden, the brand Rohypnol has been withdrawn from the domestic market. Instead it is marketed under the brand-name Flunitrazepam.
  • In Mexico, Rohypnol is approved for medical use[9], however there has been many cases of trafficking of Rohypnol to the United States and other developed nations, most of it originating from Mexico[10].
  • In Germany, flunitrazepam is available as the Roche-Brand Rohypnol 1 mg Film-Coated Tablets and several generic 1 mg tablets (e.g. Fluninoc, Flunitrazepam ratiopharm, Flunitrazepam neuraxpharm). The prescription of flunitrazepam as a hypnotic is generally tended to be for short-term treatment of severe insomnias, that are not responsive to other hypnotics (though some physicians prescribe this preparate as the ultimate high-potency hypnotic in severe cases of insomnia even as first-line option), especially in inpatients. It is considered the most potent benzodiazepine hypnotic (rather on effect than on dose basis; i.e., its hypnotic effect is being considered the most strongly pronounced of all benzodiazepine hypnotics available). Abuse of flunitrazepam among drug addicts is considerable and any possession of flunitrazepam without a valid prescription is illegal.

Abuse potentialEdit

Rohypnol2
Rohypnol
PhloxBotAdded by PhloxBot

Despite the fact that flunitrazepam is a Schedule IV controlled substance, it is not commercially available in the United States. Currently the DEA is recommending that Rohypnol be reclassified to Schedule I.

Drug-facilitated sexual assaultEdit

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. This effect is particularly dangerous when flunitrazepam is used to aid in the commission of sexual assault; victims may not be able to clearly recall the assault, the assailant, or the events surrounding the assault.

It is difficult to estimate just how many flunitrazepam-facilitated rapes have occurred in the past. Very often, biological samples are taken from the victim at a time when the effects of the drug have already passed and only residual amounts remain in the body fluids. These residual amounts are difficult, and sometimes impossible, to detect using standard screening assays available in the United States. If flunitrazepam exposure is to be detected at all, urine samples need to be collected within 72 hours and subjected to sensitive analytical tests. The problem is compounded by the onset of amnesia after ingestion of the drug, which causes the victim to be uncertain about the facts surrounding the rape. This uncertainty may lead to critical delays or even reluctance to report the rape and provide appropriate biological samples for testing. If a person suspects that he or she is the victim of a flunitrazepam-facilitated rape, he or she should get laboratory testing for flunitrazepam as soon as possible. In recent news it has been discovered that scientists can now detect flunitrazepam and related compounds in urine at least up to 5 days after administration of a single dose of Rohypnol and up to a month in hair. [1]

It must be noted that an inability to remember events, including sexual encounters, is not conclusive evidence of having consumed a drugged drink: Drunkenness itself causes blackouts, sleepiness, and a reduction in inhibitions. Only a timely screening for flunitrazepam can demonstrate its use. It has been shown that alcohol alone is the substance used in the vast majority of cases of date-rape. A recent study conducted by doctors in the U.K. found that none of the subjects reporting spiked drinks had any traces of flunitrazepam or other medications popularly believed to be associated with rape such as GHB. The study claims that binge drinking was to blame. [2]

Drug-facilitated robberyEdit

In the United Kingdom, the use of flunitrazepam and other date rape drugs has been connected to stealing from sedated victims. One expert quoted in a British tabloid estimated that up to 2,000 individuals are robbed each year after being spiked with powerful sedatives [3], making drug-assisted robbery a more common problem than drug-assisted rape.

Criminals sometimes use flunitrazepam before committing robbery as it has a calming and anti-emotive effect. This allows the criminal to perform the robbery without becoming anxious. Flunitrazepam is also known to induce anterograde amnesia making police interrogations more difficult.[11][12][13]


Recreational drugEdit

Although flunitrazepam has become widely known in USA for its use as a date-rape drug, it is used more frequently as a recreational drug. It is used by high school and college students, rave party attendees, and heroin and cocaine users (who call a dose of flunitrazepam a "roofie") for recreational purposes, including:

  • To produce profound intoxication (Kurt Cobain overdosed on a mixture of flunitrazepam and champagne several weeks before his death)
  • To boost the high produced by heroin, or ease the anxiety and/or sleeplessness of withdrawal
  • To counteract the side effects of stimulants (e.g. insomnia, paranoia, jitteriness)
  • To "soften" the so-called "crash" which follows heavy usage of stimulants, such as cocaine or methamphetamine
  • To improve sex drive and appetite.[How to reference and link to summary or text]

Flunitrazepam is usually consumed orally, and is often combined with alcohol. It is also occasionally insufflated (i.e. tablets are crushed into powder and snorted). In some European countries, there was an alcohol solution of flunitrazepam (Darkene), taken by injection, with very strong effects.

Side effectsEdit

Flunitrazepam is considered to be one of the most addictive of the benzodiazepines, along with clonazepam, bromazepam, alprazolam, and particularily, temazepam, nitrazepam, and nimetazepam. Its use causes several notable side effects, including:

Long-term use of flunitrazepam can result in psychological and physical dependence and the appearance of withdrawal symptoms when the drug is discontinued. Flunitrazepam impairs cognitive and psychomotor functions, affecting reaction time and driving skill. The use of this drug in combination with alcohol potentiates these side effects, and can lead to toxicity.

Legal statusEdit

Flunitrazepam is currently a Schedule III drug under the international Convention on Psychotropic Substances of 1971 [4]; in the United States, it is on Schedule IV

According to FDA Associate Director for Domestic and International Drug Control Nicholas Reuter[5]:

Flunitrazepam was "temporarily controlled in Schedule IV pursuant to a treaty obligation under the 1971 Convention on Psychotropic Substances. At the time flunitrazepam was placed temporarily in Schedule IV . . . there was no evidence of abuse or trafficking of the drug in the United States."

Rohypnol is currently under consideration to be rescheduled to Schedule I, and is already considered such in the States of Florida, Idaho, Minnesota, New Hampshire, New Mexico, North Dakota, Oklahoma, and Pennsylvania.

21 U.S.C. § 841

and 21 U.S.C. § 952
provide for stiff prison terms for the possession of flunitrazepam; penalties for use or distribution include life in prison, should death or serious injury occur.

In Australia, flunitrazepam is a schedule 8 drug, along with amphetamines and narcotic analgesics. All other benzodiazepines are schedule 4 drugs. Unauthorized possession of certain quantities of the drug is punishable by criminal sanctions in New South Wales under Schedule 1 of the Drug Misuse and Trafficking Act 1985.

Street termsEdit

Street names for Rohypnol include rophy, rufflels, roofies, ruffies, ruff up, rib, roach 2, R2, R2-Do-U, roche, rope, ropies, circles, circes, forget it, forget-me-pill, forget-me-now, Baptist Communion, and Mexican Valium.[14]

See also Edit

ReferencesEdit

  • Inchem - Retrieved 2007-2-27

FootnotesEdit

  1. Cano, J. P., Soliva, M.; Hartmann, D.; Ziegler, W. H.; Amrein, R. (1977). Bioavailability from various galenic formulations of flunitrazepam. Arzneimittelforschung 27 (12): 2383-8.. rohypnol.
  2. http://www.usdoj.gov/dea/pubs/rohypnol/rohypnol.htm
  3. http://www.usdoj.gov/ndic/pubs6/6074/index.htm
  4. http://www.4woman.gov/faq/rohypnol.htm
  5. includeonly>"UK Rohypnol: The date rape drug", BBC News Online, Thursday, May 20, 1999. Retrieved on 2006-03-13.
  6. (13 August 2004). Authorisation to Supply or Prescribe Drugs of Addiction: Flunitrazepam. Statutory Medical Notifications. Department of Health, Government of Western Australia. URL accessed on 2006-03-13.
  7. (August 2000). Guidelines for the Prescribing of Flunitrazepam. (PDF) Pharmaceutical Services Branch. New South Wales Health. URL accessed on 2006-03-13.
  8. (11 October 2006). Drug Wars - About Drugs.
  9. http://www.4woman.gov/faq/rohypnol.htm
  10. http://www.dea.gov/pubs/states/texas.html
  11. includeonly>"Bankrånare stärkte sig med Rohypnol?", DrugNews.
  12. includeonly>"Mijailovic var påverkad av våldsdrog", Sydsvenskan.
  13. includeonly>"Mijailovic var påverkad av våldsdrog", Expressen.
  14. Rohypnol fact sheet at About.com Teen Advice

External links Edit


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