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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
The flunitrazepam abuse prevention program at a general hospital in Taiwan: a descriptive study.
2002-08
Synthesis and preliminary pharmacological evaluation of new (+/-) 1,4-naphthoquinones structurally related to lapachol.
2002-08
Psychological stress, but not physical stress, causes increase in diazepam binding inhibitor (DBI) mRNA expression in mouse brains.
2002-07-15
Coordinate release of ATP and GABA at in vitro synapses of lateral hypothalamic neurons.
2002-06-15
Simultaneous analysis of flunitrazepam and its major metabolites in human plasma by high performance liquid chromatography tandem mass spectrometry.
2002-06-15
Detection of flunitrazepam and 7-aminoflunitrazepam in oral fluid after controlled administration of rohypnol.
2002-06-11
[Fatal outcome of poisoning with the benzodiazepines flunitrazepam and diazepam].
2002-06-05
Club drugs: methylenedioxymethamphetamine, flunitrazepam, ketamine hydrochloride, and gamma-hydroxybutyrate.
2002-06-01
More on Rohypnol.
2002-06
Tolterodine-associated acute mixed liver injury.
2002-05
Sensitive method for the detection of 22 benzodiazepines by gas chromatography-ion trap tandem mass spectrometry.
2002-04-19
Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines.
2002-04
Further comment on abnormally pigmented organs presenting at autopsy.
2002-04
Citalopram in fatal poisoning cases.
2002-03-28
Plasticity of GABA(a) system during ageing: focus on vestibular compensation and possible pharmacological intervention.
2002-03-01
Drugged and sexually assaulted.
2002-03
Flunitrazepam-membrane non-specific binding and unbinding: two pathways with different energy barriers.
2002-02-19
Mechanism of alpha-subunit selectivity of benzodiazepine pharmacology at gamma-aminobutyric acid type A receptors.
2002-02-15
[Acute ischemia of the leg in a drug addict].
2002-02
[Clonidine vs. Midazolam for premedication - comparison of the anxiolytic effect by using the STAI-test].
2002-02
Serum and urine concentrations of flunitrazepam and metabolites, after a single oral dose, by immunoassay and GC-MS.
2002-01-05
Binding and neuropharmacological profile of zaleplon, a novel nonbenzodiazepine sedative/hypnotic.
2002-01-02
Buprenorphine prescription by general practitioners in a French region.
2002-01-01
Modulation of radioligand binding to the GABA(A)-benzodiazepine receptor complex by a new component from Cyperus rotundus.
2002-01
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.
2002-01
Gamma-aminobutyric acidA and benzodiazepine receptor alterations in the rat brain after unilateral 6-hydroxydopamine lesions of the medial forebrain bundle.
2002-01
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
A novel approach to the prevention of postoperative delirium in the elderly after gastrointestinal surgery.
2002
[Crime under the influence of psychoactive drugs: the problem of the duration of detection].
2002
Acrylamide disturbs the subcellular distribution of GABAA receptor in brain neurons.
2002
Simultaneous determination of fifteen low-dosed benzodiazepines in human urine by solid-phase extraction and gas chromatography-mass spectrometry.
2001-12-25
Binding of [3H]CB 34, a selective ligand for peripheral benzodiazepine receptors, to rat brain membranes.
2001-12-07
Losigamone. Dr Willmar Schwabe.
2001-12
Density and distribution of hippocampal neurotransmitter receptors in autism: an autoradiographic study.
2001-12
Mercury interaction with the GABA(A) receptor modulates the benzodiazepine binding site in primary cultures of mouse cerebellar granule cells.
2001-12
3Alpha-hydroxy-5alpha-pregnan-20-one levels and GABA(A) receptor-mediated 36Cl(-) flux across development in rat cerebral cortex.
2001-11-26
Determination of benzodiazepines in human hair by on-line high-performance liquid chromatography using a restricted access extraction column.
2001-11-15
Evidence for the formation of functionally distinct alphabetagammaepsilon GABA(A) receptors.
2001-11-15
Characterization of [3H]flunitrazepam binding to melanin.
2001-11-15
Flunitrazepam: an evaluation of use, abuse and toxicity.
2001-11-01
Modulation of rate of onset and intensity of drug effects reduces abuse potential in healthy males.
2001-11-01
Influence of membrane cholesterol on modulation of the GABA(A) receptor by neuroactive steroids and other potentiators.
2001-11
Olanzapine-induced retarded ejaculation: role of paroxetine comedication? A case report.
2001-10-27
Evidence for a role for GABA(A) and NMDA receptors in ethanol inhibition of long-term potentiation.
2001-10-19
[Tetraplegia in the course of coma from drug intoxication].
2001-10
[Clinical aspects of abuse drugs mainly used by adolescents].
2001-10
Pressure-sensitive and -insensitive coupling in gamma-aminobutyric acid(A) receptors.
2001-10
3H-nicotine, 3H-flunitrazepam, and 3H-cocaine incorporation into melanin: a model for the examination of drug-melanin interactions.
2001-10
Mutagenesis of the GABA(A) receptor alpha1 subunit reveals a domain that affects sensitivity to GABA and benzodiazepine-site ligands.
2001-10
Synergistic protection of allopregnanolone and phenobarbital against maximal electroshock seizures in mice.
2001-04
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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