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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12FN3O3
Molecular Weight 313.2832
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUNITRAZEPAM

SMILES

CN1C2=CC=C(C=C2C(=NCC1=O)C3=CC=CC=C3F)[N+]([O-])=O

InChI

InChIKey=PPTYJKAXVCCBDU-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C16H12FN3O3
Molecular Weight 313.2832
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://en.pharmacodia.com/yaodu/html/v1/chemicals/f0782c53cab465685c663c70eb6d85e5.html | https://www.drugs.com/illicit/rohypnol.html

Flunitrazepam is an intermediate-acting benzodiazepine with general properties similar to those of diazepam. It is generally intended to be for short-term treatment for chronic or severe insomniacs who are unresponsive to other hypnotics. The main pharmacological effects of Flunitrazepam are the enhancement of GABA at the GABAA receptor. The physical effects of Flunitrazepam include sedation, muscle relaxation, decreased anxiety, and prevention of convulsions. It causes partial amnesia; individuals are unable to remember certain events that they experience while under the influence of the drug. Chronic use of Flunitrazepam can result in physical dependence and the appearance of a withdrawal syndrome 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 is a particular concern as both central nervous system depressants potentiate each other's toxicity.

Originator

Curator's Comment: # Hoffmann La Roche

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2095172
Sources: DOI: 10.1111/j.1440-1681.2008.04946.x
0.45 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Rohypnol

Approved Use

Rohypnol is generally intended to be for short-term treatment for chronic or severe insomniacs who are unresponsive to other hypnotics.

Launch Date

1982
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
21.7 ng/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
10.2 ng/mL
2 mg 1 times / day multiple, oral
dose: 2 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
FLUNITRAZEPAM blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
12.2 ng/mL
2 mg 1 times / day steady-state, oral
dose: 2 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUNITRAZEPAM blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
12.9 ng/mL
2 mg 1 times / day steady-state, oral
dose: 2 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUNITRAZEPAM blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
47.5 ng/mL
2 mg single, intravenous
dose: 2 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
11.5 ng/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
25 ng/mL
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
12.9 ng/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
13.1 ng/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
9.2 ng/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
203 ng × h/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
232.8 ng × h/mL
2 mg single, intravenous
dose: 2 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
116.7 ng × h/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
240.2 ng × h/mL
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
21.2 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
24 h
2 mg single, intravenous
dose: 2 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.8 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.2 h
4 mg single, oral
dose: 4 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
22.5 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
25.3 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
20.2 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUNITRAZEPAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
20.4%
FLUNITRAZEPAM plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
8 mg 1 times / day multiple, oral
Highest studied dose
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Other AEs: Drowsiness, Hypotonia...
Other AEs:
Drowsiness
Hypotonia
Sources:
1.3 mg/kg single, intravenous
Highest studied dose
Dose: 1.3 mg/kg
Route: intravenous
Route: single
Dose: 1.3 mg/kg
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Other AEs: Respiratory depression...
Other AEs:
Respiratory depression
Sources:
AEs

AEs

AESignificanceDosePopulation
Drowsiness
8 mg 1 times / day multiple, oral
Highest studied dose
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Hypotonia
8 mg 1 times / day multiple, oral
Highest studied dose
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Respiratory depression
1.3 mg/kg single, intravenous
Highest studied dose
Dose: 1.3 mg/kg
Route: intravenous
Route: single
Dose: 1.3 mg/kg
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Synergistic protection of allopregnanolone and phenobarbital against maximal electroshock seizures in mice.
2001 Apr
Semiautomated high-performance liquid chromatographic method for the determination of benzodiazepines in whole blood.
2001 Apr
High-performance liquid chromatography determination of flunitrazepam and its metabolites in plasma by use of column-switching technique: comparison of two extraction columns.
2001 Apr 25
[Clonidine combined with flunitrazepam before carotid endarterectomy decreases cerebrovascular CO2 reactivity].
2001 Aug
Flunitrazepam abuse and personality characteristics in male forensic psychiatric patients.
2001 Aug 5
Losigamone. Dr Willmar Schwabe.
2001 Dec
Density and distribution of hippocampal neurotransmitter receptors in autism: an autoradiographic study.
2001 Dec
Mercury interaction with the GABA(A) receptor modulates the benzodiazepine binding site in primary cultures of mouse cerebellar granule cells.
2001 Dec
Simultaneous determination of fifteen low-dosed benzodiazepines in human urine by solid-phase extraction and gas chromatography-mass spectrometry.
2001 Dec 25
Binding of [3H]CB 34, a selective ligand for peripheral benzodiazepine receptors, to rat brain membranes.
2001 Dec 7
Activation of GABA(A) receptors in subthalamic neurons in vitro: properties of native receptors and inhibition mechanisms.
2001 Jul
Drug-facilitated date rape.
2001 Jul 10
Olanzapine-induced retarded ejaculation: role of paroxetine comedication? A case report.
2001 Jul-Aug
Atrial flutter in fetuses and early childhood: a report of eight cases.
2001 Jun
Drug-facilitated sexual assault.
2001 Jun
Patient information. Date rape drugs: what parents should know.
2001 Jun
Differential sensitivity to the anxiolytic effects of ethanol and flunitrazepam in PKCgamma null mutant mice.
2001 May-Jun
Pharmacodynamic and receptor binding changes during chronic lorazepam administration.
2001 May-Jun
Influence of membrane cholesterol on modulation of the GABA(A) receptor by neuroactive steroids and other potentiators.
2001 Nov
Flunitrazepam: an evaluation of use, abuse and toxicity.
2001 Nov 1
Modulation of rate of onset and intensity of drug effects reduces abuse potential in healthy males.
2001 Nov 1
Determination of benzodiazepines in human hair by on-line high-performance liquid chromatography using a restricted access extraction column.
2001 Nov 15
Evidence for the formation of functionally distinct alphabetagammaepsilon GABA(A) receptors.
2001 Nov 15
Characterization of [3H]flunitrazepam binding to melanin.
2001 Nov 15
3Alpha-hydroxy-5alpha-pregnan-20-one levels and GABA(A) receptor-mediated 36Cl(-) flux across development in rat cerebral cortex.
2001 Nov 26
Serum and urine concentrations of flunitrazepam and metabolites, after a single oral dose, by immunoassay and GC-MS.
2001 Nov-Dec
[Tetraplegia in the course of coma from drug intoxication].
2001 Oct
[Clinical aspects of abuse drugs mainly used by adolescents].
2001 Oct
Pressure-sensitive and -insensitive coupling in gamma-aminobutyric acid(A) receptors.
2001 Oct
3H-nicotine, 3H-flunitrazepam, and 3H-cocaine incorporation into melanin: a model for the examination of drug-melanin interactions.
2001 Oct
Mutagenesis of the GABA(A) receptor alpha1 subunit reveals a domain that affects sensitivity to GABA and benzodiazepine-site ligands.
2001 Oct
Evidence for a role for GABA(A) and NMDA receptors in ethanol inhibition of long-term potentiation.
2001 Oct 19
Deposition of 7-aminoflunitrazepam and flunitrazepam in hair after a single dose of Rohypnol.
2001 Sep
Lack of allosteric modulation of striatal GABA(A) receptor binding and function after cocaine sensitization.
2001 Sep
Distinct signal transduction pathways for GABA-induced GABA(A) receptor down-regulation and uncoupling in neuronal culture: a role for voltage-gated calcium channels.
2001 Sep
Sensitive method for the detection of 22 benzodiazepines by gas chromatography-ion trap tandem mass spectrometry.
2002 Apr 19
[Clonidine vs. Midazolam for premedication - comparison of the anxiolytic effect by using the STAI-test].
2002 Feb
Mechanism of alpha-subunit selectivity of benzodiazepine pharmacology at gamma-aminobutyric acid type A receptors.
2002 Feb 15
Modulation of radioligand binding to the GABA(A)-benzodiazepine receptor complex by a new component from Cyperus rotundus.
2002 Jan
Role of the histidine residue at position 105 in the human alpha 5 containing GABA(A) receptor on the affinity and efficacy of benzodiazepine site ligands.
2002 Jan
Gamma-aminobutyric acidA and benzodiazepine receptor alterations in the rat brain after unilateral 6-hydroxydopamine lesions of the medial forebrain bundle.
2002 Jan
Buprenorphine prescription by general practitioners in a French region.
2002 Jan 1
Binding and neuropharmacological profile of zaleplon, a novel nonbenzodiazepine sedative/hypnotic.
2002 Jan 2
Psychological stress, but not physical stress, causes increase in diazepam binding inhibitor (DBI) mRNA expression in mouse brains.
2002 Jul 15
Club drugs: methylenedioxymethamphetamine, flunitrazepam, ketamine hydrochloride, and gamma-hydroxybutyrate.
2002 Jun 1
Coordinate release of ATP and GABA at in vitro synapses of lateral hypothalamic neurons.
2002 Jun 15
Simultaneous analysis of flunitrazepam and its major metabolites in human plasma by high performance liquid chromatography tandem mass spectrometry.
2002 Jun 15
Drugged and sexually assaulted.
2002 Mar
Plasticity of GABA(a) system during ageing: focus on vestibular compensation and possible pharmacological intervention.
2002 Mar 1
Citalopram in fatal poisoning cases.
2002 Mar 28
Patents

Sample Use Guides

Usual dose 0.5 - 1mg; in exceptional circumstances the dose may be increased to 2mg.
Route of Administration: Oral
The binding affinity for [3H]flunitrazepam was most affected in the hippocampus where there was a significant drug ×time interaction (F4,49= 4.6, p<0.01).
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:46:03 GMT 2025
Edited
by admin
on Mon Mar 31 17:46:03 GMT 2025
Record UNII
620X0222FQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ROHYPNOL
Preferred Name English
FLUNITRAZEPAM
EP   HSDB   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
FLUNITRAZEPAM [USAN]
Common Name English
FLUNITRAZEPAM [EP MONOGRAPH]
Common Name English
2H-1,4-BENZODIAZEPIN-2-ONE, 5-(2-FLUOROPHENYL)-1,3-DIHYDRO-1-METHYL-7-NITRO-
Systematic Name English
RO-54200
Code English
5-(O-FLUOROPHENYL)-1,3-DIHYDRO-1-METHYL-7-NITRO-2H-1,4-BENZODIAZEPIN-2-ONE
Common Name English
Flunitrazepam [WHO-DD]
Common Name English
FLUNITRAZEPAM [MI]
Common Name English
FLUNITRAZEPAM [HSDB]
Common Name English
FLUNITRAZEPAM [JAN]
Common Name English
flunitrazepam [INN]
Common Name English
FLUNITRAZEPAM [MART.]
Common Name English
RO-5-4200
Code English
RO 5-4200
Code English
N05CD03
Code English
Classification Tree Code System Code
WHO-VATC QN05CD03
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
DEA NO. 2763
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
NCI_THESAURUS C1012
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
WHO-ATC N05CD03
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
Code System Code Type Description
IUPHAR
4193
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
FDA UNII
620X0222FQ
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
MERCK INDEX
m5447
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL13280
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
DRUG CENTRAL
1202
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
CAS
1622-62-4
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PRIMARY
EPA CompTox
DTXSID7023065
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
SMS_ID
100000092658
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
CHEBI
31622
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
HSDB
6960
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
PUBCHEM
3380
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
RXCUI
4460
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY RxNorm
WIKIPEDIA
FLUNITRAZEPAM
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
INN
2951
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
DRUG BANK
DB01544
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
MESH
D005445
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
NCI_THESAURUS
C87672
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
ECHA (EC/EINECS)
216-597-8
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
EVMPD
SUB07710MIG
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
LACTMED
Flunitrazepam
Created by admin on Mon Mar 31 17:46:03 GMT 2025 , Edited by admin on Mon Mar 31 17:46:03 GMT 2025
PRIMARY
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