Flunitrazepam

Flunitrazepam
Clinical data
Pronunciation/ˌflnɪˈtræzɪpæm/
Trade namesRohypnol
Other namesroofies, floonies
Pregnancy
category
  • AU: C
Addiction
liability
High[1]
Routes of
administration
Oral
Drug classBenzodiazepine
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability64–77% (by mouth)
50% (suppository)
MetabolismLiver
Metabolites7-aminoflunitrazepam, desmethylflunitrazepam and 3-hydroxydesmethylflunitrazepam
Elimination half-life18–26 hours
ExcretionKidney
Identifiers
  • 5-(2-fluorophenyl)-1-methyl-7-nitro-1H-benzo[e][1,4]diazepin-2(3H)-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.015.089 Edit this at Wikidata
Chemical and physical data
FormulaC16H12FN3O3
Molar mass313.288 g·mol−1
3D model (JSmol)
Melting point170–172 °C (338–342 °F)
  • CN1C(=O)CN=C(c2ccccc2F)c2cc([N+](=O)[O-])ccc21
  • InChI=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 checkY
  • Key:PPTYJKAXVCCBDU-UHFFFAOYSA-N checkY
  (verify)

Flunitrazepam, sold under the brand name Rohypnol among others,[3] is a benzodiazepine used to treat severe insomnia and assist with anesthesia.[4] As with other hypnotics, flunitrazepam has been advised to be prescribed only for short-term use or by those with chronic insomnia on an occasional basis.[4]

It was patented in 1962 and came into medical use in 1974.[5] Flunitrazepam, nicknamed "roofies" or "floonies", is widely known for its use as a date rape drug.[6][7]

  1. ^ Ries RK (2009). Principles of addiction medicine (4 ed.). Philadelphia: Wolters Kluwer/Lippincott Williams & Wilkins. p. 106. ISBN 978-0-7817-7477-2. Archived from the original on September 8, 2017.
  2. ^ Anvisa (March 31, 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published April 4, 2023). Archived from the original on August 3, 2023. Retrieved August 16, 2023.
  3. ^ Cite error: The named reference generics was invoked but never defined (see the help page).
  4. ^ a b "Prescribing of Benzodiazepines Alprazolam and Flunitrazepam" (PDF). Pharmaceutical Services Branch. New South Wales Health. November 2013. Archived (PDF) from the original on June 23, 2014.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 53X. ISBN 9783527607495.
  6. ^ Schwartz RH, Milteer R, LeBeau MA (June 2000). "Drug-facilitated sexual assault ('date rape')". Southern Medical Journal. 93 (6): 558–561. doi:10.1097/00007611-200093060-00002. PMID 10881768.
  7. ^ Gautam L, Sharratt SD, Cole MD (February 19, 2014). "Drug facilitated sexual assault: detection and stability of benzodiazepines in spiked drinks using gas chromatography-mass spectrometry". PLOS ONE. 9 (2): e89031. Bibcode:2014PLoSO...989031G. doi:10.1371/journal.pone.0089031. PMC 3929633. PMID 24586489.

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