U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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=C(C=C(C=C2)[N+]([O-])=O)C(=NCC1=O)C3=C(F)C=CC=C3

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.

CNS Activity

Originator

Hoffman-La Roche
143
Curator's Comment: # Hoffmann La Roche

Approval Year

Unknown
134361
Targets

Targets

Primary TargetPharmacologyConditionPotency
Positive Allosteric Modulator
179
GABA-A receptor; alpha-1/beta-2/gamma-2
27
Target ID: CHEMBL2095172
Sources: DOI: 10.1111/j.1440-1681.2008.04946.x
Positive Allosteric Modulator
179
 0.45 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
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

3.92515191E11
PubMed

PubMed

TitleDatePubMed
Synergistic protection of allopregnanolone and phenobarbital against maximal electroshock seizures in mice.
2001 Apr
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
Olanzapine-induced retarded ejaculation: role of paroxetine comedication? A case report.
2001 Jul-Aug
Differential sensitivity to the anxiolytic effects of ethanol and flunitrazepam in PKCgamma null mutant mice.
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
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
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
Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines.
2002 Apr
Further comment on abnormally pigmented organs presenting at autopsy.
2002 Apr
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
[Acute ischemia of the leg in a drug addict].
2002 Feb
[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
Flunitrazepam-membrane non-specific binding and unbinding: two pathways with different energy barriers.
2002 Feb 19
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
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
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
[Fatal outcome of poisoning with the benzodiazepines flunitrazepam and diazepam].
2002 Mar-Apr
Tolterodine-associated acute mixed liver injury.
2002 May
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 Jul 05 22:37:26 UTC 2023
Edited
by admin
on Wed Jul 05 22:37:26 UTC 2023
Record UNII
620X0222FQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
ROHYPNOL
Brand 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 Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
DEA NO. 2763
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
NCI_THESAURUS C1012
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
WHO-ATC N05CD03
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
Code System Code Type Description
IUPHAR
4193
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
FDA UNII
620X0222FQ
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
MERCK INDEX
M5447
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL13280
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
DRUG CENTRAL
1202
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
CAS
1622-62-4
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
EPA CompTox
DTXSID7023065
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
SMS_ID
100000092658
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
CHEBI
31622
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
HSDB
6960
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
PUBCHEM
3380
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
RXCUI
4460
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
FLUNITRAZEPAM
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
INN
2951
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
DRUG BANK
DB01544
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
MESH
D005445
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
NCI_THESAURUS
C87672
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
ECHA (EC/EINECS)
216-597-8
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
EVMPD
SUB07710MIG
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
LACTMED
Flunitrazepam
Created by admin on Wed Jul 05 22:37:26 UTC 2023 , Edited by admin on Wed Jul 05 22:37:26 UTC 2023
PRIMARY
Related Record Type Details
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Structure of FLUNITRAZEPAM HYDROCHLORIDE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
GAMMA-AMINOBUTYRIC ACID RECEPTOR SUBUNIT ALPHA-6
TARGET -> ACTIVATOR
Related Record Type Details
Structure of 7-AMINOFLUNITRAZEPAM
METABOLITE -> PARENT
Structure of NORFLUNITRAZEPAM
METABOLITE -> PARENT
MAJOR
URINE
Structure of 3-HYDROXYFLUNITRAZEPAM
METABOLITE -> PARENT
MAJOR
Related Record Type Details
Structure of 2′-Fluoro-2-methylamino-5-nitrobenzophenone
IMPURITY -> PARENT
Structure of 3-amino-4-(2-fluorophenyl)-1-methyl-6-nitroquinolin-2(1H)-one
IMPURITY -> PARENT
Structure of 7-Aminodemethylflunitrazepam
IMPURITY -> PARENT
Structure of NORFLUNITRAZEPAM
IMPURITY -> PARENT
not more than the area of principal peak in the chromatogram obtained with reference solution (a) (0.1 per cent)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of FLUNITRAZEPAM
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966