Flunitrazepam

Flunitrazepam

Clinical data
Pronunciation	/ˌfluːnᵻˈtræzᵻpæm/
Trade names	Rohypnol
Pregnancy category	AU: C
Dependence liability	Very high
Routes of administration	Oral (tablets)
ATC code	N05CD03 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage III (Prescription only) UK: Class C US: Schedule IV UN: Psychotropic Schedule III
Pharmacokinetic data
Bioavailability	64–77% (oral) 50% (suppository)
Metabolism	Hepatic
Biological half-life	18–26 hours
Excretion	Renal
Identifiers
IUPAC name 5-(2-fluorophenyl)-1-methyl-7-nitro-1H-benzo[e][1,4]diazepin-2(3H)-one
CAS Number	1622-62-4 Y
PubChem CID	3380
IUPHAR/BPS	4193
DrugBank	DB01544 Y
ChemSpider	3263 Y
UNII	620X0222FQ
KEGG	D01230 Y
ChEMBL	CHEMBL13280 Y
ECHA InfoCard	100.015.089
Chemical and physical data
Formula	C16H12FN3O3
Molar mass	313.3 g/mol
3D model (Jmol)	Interactive image
SMILES [O-][N+](C1=CC2=C(C=C1)N(C)C(CN=C2C3=CC=CC=C3F)=O)=O
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 Y Key:PPTYJKAXVCCBDU-UHFFFAOYSA-N Y

Flunitrazepam, also known as Rohypnol among other names, is an intermediate acting benzodiazepine used in some countries to treat severe insomnia and in fever, early in anesthesia. Just as with other hypnotics, flunitrazepam should be strictly used only on a short-term basis or by those with chronic insomnia on an occasional basis. Flunitrazepam has been referred to as a date rape drug even though its incidence is very rare in cases that have been reported. Along with GHB, MDMA and ketamine, Rohypnol is considered to be a club drug, due to its recreational use by dancers at raves, nightclubs and electronic dance music festivals.

In countries where the drug is still used, it is used for treatment of insomnia, and in some countries to begin anesthesia as well; these were also the indications in which it was originally studied.

Adverse 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.

Flunitrazepam as with other benzodiazepines can lead to drug dependence and benzodiazepine withdrawal syndrome.

Discontinuation may result in the appearance of withdrawal symptoms when the drug is discontinued. Abrupt withdrawal may lead to a benzodiazepine withdrawal syndrome characterised by seizures, psychosis, insomnia, and anxiety. Rebound insomnia, worse than baseline insomnia, typically occur after discontinuation of flunitrazepam even after short-term single nightly dose therapy.