FLUNITRAZEPAM

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 Search

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
Sources: http://www.medicines.ie/printfriendlydocument.aspx?documentid=1048&companyid=264
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11393809 \| https://www.ncbi.nlm.nih.gov/pubmed/9914279	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

Condition	Modality	Targets	Highest Phase	Product
Insomnia 111 Sources: http://www.medicines.ie/printfriendlydocument.aspx?documentid=1048&companyid=264	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

C_max

Value	Dose	Analyte	Population
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

Value	Dose	Analyte	Population
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

T_1/2

Value	Dose	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Dose	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2B6 776 CYP2E1 729 P-gp 2052 CYP2C19 1119 CYP1A2 1197 CYP2A6 626 CYP2C8 810

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11159802/	major [Km 155 uM]
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11159802/	minor [Km 101 uM]
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11159802/	minor [Km 1921 uM]
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11159802/	minor [Km 50 uM]
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11159802/	minor [Km 60 uM]
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8647944/	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11159802/	unlikely
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11159802/	unlikely
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11159802/	unlikely
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11159802/	unlikely

PubMed

Title	Date	PubMed
Synergistic protection of allopregnanolone and phenobarbital against maximal electroshock seizures in mice.	2001 Apr	11742590
Semiautomated high-performance liquid chromatographic method for the determination of benzodiazepines in whole blood.	2001 Apr	11327354
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	11339271
[Clonidine combined with flunitrazepam before carotid endarterectomy decreases cerebrovascular CO2 reactivity].	2001 Aug	11530748
Flunitrazepam abuse and personality characteristics in male forensic psychiatric patients.	2001 Aug 5	11472788
Losigamone. Dr Willmar Schwabe.	2001 Dec	11892943
Density and distribution of hippocampal neurotransmitter receptors in autism: an autoradiographic study.	2001 Dec	11814263
Mercury interaction with the GABA(A) receptor modulates the benzodiazepine binding site in primary cultures of mouse cerebellar granule cells.	2001 Dec	11684146
Simultaneous determination of fifteen low-dosed benzodiazepines in human urine by solid-phase extraction and gas chromatography-mass spectrometry.	2001 Dec 25	11767312
Binding of [3H]CB 34, a selective ligand for peripheral benzodiazepine receptors, to rat brain membranes.	2001 Dec 7	11740947
Activation of GABA(A) receptors in subthalamic neurons in vitro: properties of native receptors and inhibition mechanisms.	2001 Jul	11431489
Drug-facilitated date rape.	2001 Jul 10	11468961
Olanzapine-induced retarded ejaculation: role of paroxetine comedication? A case report.	2001 Jul-Aug	11677871
Atrial flutter in fetuses and early childhood: a report of eight cases.	2001 Jun	11529363
Drug-facilitated sexual assault.	2001 Jun	11440338
Patient information. Date rape drugs: what parents should know.	2001 Jun	11405617
Differential sensitivity to the anxiolytic effects of ethanol and flunitrazepam in PKCgamma null mutant mice.	2001 May-Jun	11420074
Pharmacodynamic and receptor binding changes during chronic lorazepam administration.	2001 May-Jun	11420062
Influence of membrane cholesterol on modulation of the GABA(A) receptor by neuroactive steroids and other potentiators.	2001 Nov	11704651
Flunitrazepam: an evaluation of use, abuse and toxicity.	2001 Nov 1	11672967
Modulation of rate of onset and intensity of drug effects reduces abuse potential in healthy males.	2001 Nov 1	11672943
Determination of benzodiazepines in human hair by on-line high-performance liquid chromatography using a restricted access extraction column.	2001 Nov 15	11731192
Evidence for the formation of functionally distinct alphabetagammaepsilon GABA(A) receptors.	2001 Nov 15	11711565
Characterization of [3H]flunitrazepam binding to melanin.	2001 Nov 15	11700981
3Alpha-hydroxy-5alpha-pregnan-20-one levels and GABA(A) receptor-mediated 36Cl(-) flux across development in rat cerebral cortex.	2001 Nov 26	11718833
Serum and urine concentrations of flunitrazepam and metabolites, after a single oral dose, by immunoassay and GC-MS.	2001 Nov-Dec	11765027
[Tetraplegia in the course of coma from drug intoxication].	2001 Oct	11695294
[Clinical aspects of abuse drugs mainly used by adolescents].	2001 Oct	11668269
Pressure-sensitive and -insensitive coupling in gamma-aminobutyric acid(A) receptors.	2001 Oct	11605100
3H-nicotine, 3H-flunitrazepam, and 3H-cocaine incorporation into melanin: a model for the examination of drug-melanin interactions.	2001 Oct	11599608
Mutagenesis of the GABA(A) receptor alpha1 subunit reveals a domain that affects sensitivity to GABA and benzodiazepine-site ligands.	2001 Oct	11595757
Evidence for a role for GABA(A) and NMDA receptors in ethanol inhibition of long-term potentiation.	2001 Oct 19	11597760
Deposition of 7-aminoflunitrazepam and flunitrazepam in hair after a single dose of Rohypnol.	2001 Sep	11569557
Lack of allosteric modulation of striatal GABA(A) receptor binding and function after cocaine sensitization.	2001 Sep	11566142
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	11553685
Sensitive method for the detection of 22 benzodiazepines by gas chromatography-ion trap tandem mass spectrometry.	2002 Apr 19	12058908
[Clonidine vs. Midazolam for premedication - comparison of the anxiolytic effect by using the STAI-test].	2002 Feb	11865386
Mechanism of alpha-subunit selectivity of benzodiazepine pharmacology at gamma-aminobutyric acid type A receptors.	2002 Feb 15	11864636
Modulation of radioligand binding to the GABA(A)-benzodiazepine receptor complex by a new component from Cyperus rotundus.	2002 Jan	11824542
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	11786501
Gamma-aminobutyric acidA and benzodiazepine receptor alterations in the rat brain after unilateral 6-hydroxydopamine lesions of the medial forebrain bundle.	2002 Jan	11783749
Buprenorphine prescription by general practitioners in a French region.	2002 Jan 1	11772481
Binding and neuropharmacological profile of zaleplon, a novel nonbenzodiazepine sedative/hypnotic.	2002 Jan 2	11755161
Psychological stress, but not physical stress, causes increase in diazepam binding inhibitor (DBI) mRNA expression in mouse brains.	2002 Jul 15	12117556
Club drugs: methylenedioxymethamphetamine, flunitrazepam, ketamine hydrochloride, and gamma-hydroxybutyrate.	2002 Jun 1	12063892
Coordinate release of ATP and GABA at in vitro synapses of lateral hypothalamic neurons.	2002 Jun 15	12077176
Simultaneous analysis of flunitrazepam and its major metabolites in human plasma by high performance liquid chromatography tandem mass spectrometry.	2002 Jun 15	12049981
Drugged and sexually assaulted.	2002 Mar	11928291
Plasticity of GABA(a) system during ageing: focus on vestibular compensation and possible pharmacological intervention.	2002 Mar 1	11852033
Citalopram in fatal poisoning cases.	2002 Mar 28	11955823

Patents

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 `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

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Name

Type

Language

ROHYPNOL

Preferred Name

English

FLUNITRAZEPAM

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