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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12FN3O3.ClH
Molecular Weight 349.744
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUNITRAZEPAM HYDROCHLORIDE

SMILES

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

InChI

InChIKey=ABHSFYRSFUICJR-UHFFFAOYSA-N
InChI=1S/C16H12FN3O3.ClH/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;1H

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
Molecular Formula ClH
Molecular Weight 36.461
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.

CNS Activity

Originator

Hoffman-La Roche
135
Curator's Comment: # Hoffmann La Roche

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Positive Allosteric Modulator
186
GABA-A receptor; alpha-1/beta-2/gamma-2
28
Target ID: CHEMBL2095172
Sources: DOI: 10.1111/j.1440-1681.2008.04946.x
Positive Allosteric Modulator
186
 0.45 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
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
OTHER GOV'T
https://www.info.pmda.go.jp/go/interview/1/170033_1124008F1024_1_020_1F.pdf#page=18
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
OTHER GOV'T
https://www.info.pmda.go.jp/go/interview/1/170033_1124008F1024_1_020_1F.pdf#page=18 | https://www.jstage.jst.go.jp/article/jscpt1970/9/3/9_3_251/_article/-char/en
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
OTHER GOV'T
https://www.info.pmda.go.jp/go/interview/1/170033_1124008F1024_1_020_1F.pdf#page=18 | https://www.jstage.jst.go.jp/article/jscpt1970/9/3/9_3_251/_article/-char/en
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
OTHER GOV'T
https://www.info.pmda.go.jp/go/interview/1/170033_1124008F1024_1_020_1F.pdf#page=18 | https://www.jstage.jst.go.jp/article/jscpt1970/9/3/9_3_251/_article/-char/en
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
EXPERIMENT
https://www.jstage.jst.go.jp/article/jscpt1970/9/3/9_3_251/_article/-char/en
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
EXPERIMENT
https://www.jstage.jst.go.jp/article/jscpt1970/9/3/9_3_251/_article/-char/en
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
EXPERIMENT
https://www.jstage.jst.go.jp/article/jscpt1970/9/3/9_3_251/_article/-char/en
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2096104/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2096104/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2096104/
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
OTHER GOV'T
https://www.info.pmda.go.jp/go/interview/1/170033_1124008F1024_1_020_1F.pdf#page=18
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
EXPERIMENT
https://www.jstage.jst.go.jp/article/jscpt1970/9/3/9_3_251/_article/-char/en
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
EXPERIMENT
https://www.jstage.jst.go.jp/article/jscpt1970/9/3/9_3_251/_article/-char/en
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
EXPERIMENT
https://www.jstage.jst.go.jp/article/jscpt1970/9/3/9_3_251/_article/-char/en
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
OTHER GOV'T
https://www.info.pmda.go.jp/go/interview/1/170033_1124008F1024_1_020_1F.pdf#page=18
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
EXPERIMENT
https://www.jstage.jst.go.jp/article/jscpt1970/9/3/9_3_251/_article/-char/en
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
EXPERIMENT
https://www.jstage.jst.go.jp/article/jscpt1970/9/3/9_3_251/_article/-char/en
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
EXPERIMENT
https://www.jstage.jst.go.jp/article/jscpt1970/9/3/9_3_251/_article/-char/en
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2096104/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2096104/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2096104/
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%
OTHER GOV'T
https://www.info.pmda.go.jp/go/interview/1/170033_1124008F1024_1_020_1F.pdf#page=19
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:
https://link.springer.com/article/10.1007/BF00429228
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://link.springer.com/article/10.1007/BF00429228
Other AEs: Drowsiness, Hypotonia...
Other AEs:
Drowsiness
Hypotonia
Sources:
https://link.springer.com/article/10.1007/BF00429228
1.3 mg/kg single, intravenous
Highest studied dose
Dose: 1.3 mg/kg
Route: intravenous
Route: single
Dose: 1.3 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8214408/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/8214408/
Other AEs: Respiratory depression...
Other AEs:
Respiratory depression
Sources:
https://pubmed.ncbi.nlm.nih.gov/8214408/
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:
https://link.springer.com/article/10.1007/BF00429228
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://link.springer.com/article/10.1007/BF00429228
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:
https://link.springer.com/article/10.1007/BF00429228
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://link.springer.com/article/10.1007/BF00429228
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:
https://pubmed.ncbi.nlm.nih.gov/8214408/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/8214408/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946
substrate
1193
substrate
1388

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2B6
776

CYP2E1
729

P-gp
2052

CYP2C19
1119

CYP1A2
1197

CYP2A6
626

CYP2C8
810
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1946
 major [Km 155 uM]
CYP2B6
776
 minor [Km 101 uM]
CYP2A6
626
 minor [Km 1921 uM]
CYP2C9
1193
 minor [Km 50 uM]
CYP2C19
1119
 minor [Km 60 uM]
P-gp
2052
 no
CYP1A2
1197
 unlikely
CYP2C8
810
 unlikely
CYP2D6
1388
 unlikely
CYP2E1
729
 unlikely
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
Flunitrazepam abuse and personality characteristics in male forensic psychiatric patients.
2001 Aug 5
Mercury interaction with the GABA(A) receptor modulates the benzodiazepine binding site in primary cultures of mouse cerebellar granule cells.
2001 Dec
Radioligand binding assays in the drug discovery process: potential pitfalls of high throughput screenings.
2001 Feb
Molecular modeling and QSAR analysis of the interaction of flavone derivatives with the benzodiazepine binding site of the GABA(A) receptor complex.
2001 Feb
CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam.
2001 Feb
[Rohypnol--a narcotic drug].
2001 Feb 21
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
Atrial flutter in fetuses and early childhood: a report of eight cases.
2001 Jun
Drug-facilitated sexual assault.
2001 Jun
Designer drugs. Assess & manage patients intoxicated with ecstasy, GHB or rohypnol--the three most commonly abused designer drugs.
2001 Jun
The association between intravenous haloperidol and prolonged QT interval.
2001 Jun
Allosteric modulation in spontaneously active mutant gamma-aminobutyric acidA receptors.
2001 Jun 1
GABA(A) receptor gene expression in rat cortex: differential effects of two chronic diazepam treatment regimes.
2001 Jun 15
Observation of psychoactive substance consumption: methods and results of the French OPPIDUM programme.
2001 Mar
[3H]Ro 15-1788 binding sites to brain membrane of the saltwater Mugil cephalus.
2001 Mar
[3H]Flunitrazepam binding to recombinant alpha1beta2gamma2S GABAA receptors stably expressed in HEK 293 cells.
2001 May
Synaptically released neurotransmitter fails to desensitize postsynaptic GABA(A) receptors in cerebellar cultures.
2001 May
In ovo chronic neurosteroid treatment affects the function and allosteric interactions of GABA(A) receptor modulatory sites.
2001 May 25
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
Determination of benzodiazepines in human hair by on-line high-performance liquid chromatography using a restricted access extraction column.
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
Deposition of 7-aminoflunitrazepam and flunitrazepam in hair after a single dose of Rohypnol.
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
Violent behavior, impulsive decision-making, and anterograde amnesia while intoxicated with flunitrazepam and alcohol or other drugs: a case study in forensic psychiatric patients.
2002
Sensitive method for the detection of 22 benzodiazepines by gas chromatography-ion trap tandem mass spectrometry.
2002 Apr 19
The flunitrazepam abuse prevention program at a general hospital in Taiwan: a descriptive study.
2002 Aug
Synthesis and preliminary pharmacological evaluation of new (+/-) 1,4-naphthoquinones structurally related to lapachol.
2002 Aug
[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
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
More on Rohypnol.
2002 Jun
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
Plasticity of GABA(a) system during ageing: focus on vestibular compensation and possible pharmacological intervention.
2002 Mar 1
Detection of flunitrazepam and 7-aminoflunitrazepam in oral fluid after controlled administration of rohypnol.
2002 May-Jun
Patents

Patents

03989681
3
JP2004269485A
5
US3116203
2
US3203990
2

Sample Use Guides

In Vivo Use Guide
Usual dose 0.5 - 1mg; in exceptional circumstances the dose may be increased to 2mg.
Route of Administration: Oral
In Vitro Use Guide
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 Wed Apr 02 12:16:40 GMT 2025
Edited
by admin
on Wed Apr 02 12:16:40 GMT 2025
Record UNII
8L46R3P7MF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2H-1,4-BENZODIAZEPIN-2-ONE, 5-(2-FLUOROPHENYL)-1,3-DIHYDRO-1-METHYL-7-NITRO-, HYDROCHLORIDE (1:1)
Preferred Name English
FLUNITRAZEPAM HYDROCHLORIDE
Common Name English
2H-1,4-BENZODIAZEPIN-2-ONE, 5-(2-FLUOROPHENYL)-1,3-DIHYDRO-1-METHYL-7-NITRO-, MONOHYDROCHLORIDE
Systematic Name English
Code System Code Type Description
FDA UNII
8L46R3P7MF
Created by admin on Wed Apr 02 12:16:40 GMT 2025 , Edited by admin on Wed Apr 02 12:16:40 GMT 2025
PRIMARY
PUBCHEM
156028042
Created by admin on Wed Apr 02 12:16:40 GMT 2025 , Edited by admin on Wed Apr 02 12:16:40 GMT 2025
PRIMARY
CAS
88280-25-5
Created by admin on Wed Apr 02 12:16:40 GMT 2025 , Edited by admin on Wed Apr 02 12:16:40 GMT 2025
PRIMARY
Related Record Type Details
Structure of FLUNITRAZEPAM
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of FLUNITRAZEPAM
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