Flunitrazepam

Flunitrazepam
Clinical data
Pronunciation	/ˌfluːnɪˈtræzɪpæm/
Trade names	Rohypnol
Other names	roofies, floonies
Pregnancy; category	AU: C;
Addiction; liability	High
Routes of; administration	Oral
Drug class	Benzodiazepine
ATC code	N05CD03 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class B1 (Psychoactive drugs); CA: Schedule I; DE: Anlage III (Special prescription form required); UK: Class C; US: Schedule IV (Schedule I trafficking penalties, however); UN: Psychotropic Schedule III; SE: Förteckning II;
Pharmacokinetic data
Bioavailability	64–77% (by mouth); 50% (suppository)
Metabolism	Liver
Metabolites	7-aminoflunitrazepam, desmethylflunitrazepam and 3-hydroxydesmethylflunitrazepam
Elimination half-life	18–26 hours
Excretion	Kidney
Identifiers
	IUPAC name 5-(2-fluorophenyl)-1-methyl-7-nitro-1H-benzo[e][1,4]diazepin-2(3H)-one;
CAS Number	1622-62-4 ;
PubChem CID	3380;
IUPHAR/BPS	4193;
DrugBank	DB01544 ;
ChemSpider	3263 ;
UNII	620X0222FQ;
KEGG	D01230 ;
ChEBI	CHEBI:31622;
ChEMBL	ChEMBL13280 ;
CompTox Dashboard (EPA)	DTXSID7023065 ;
ECHA InfoCard	100.015.089
Chemical and physical data
Formula	C16H12FN3O3
Molar mass	313.288 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	170–172 °C (338–342 °F)
	SMILES CN1C(=O)CN=C(c2ccccc2F)c2cc([N+](=O)[O-])ccc21;
	InChI 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 ; Key:PPTYJKAXVCCBDU-UHFFFAOYSA-N ;
	(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]

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

^ 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.
^ 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.
^ Cite error: The named reference generics was invoked but never defined (see the help page).
^ ^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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 53X. ISBN 9783527607495.
^ 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.
^ 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.

[Ries-2009-1] 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.

[generics-3] Cite error: The named reference generics was invoked but never defined (see the help page).

[NSW-PSB-4] "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.

[Fis2006-5] 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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