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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12FN3O3
Molecular Weight 313.2838
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUNITRAZEPAM

SMILES

CN1c2ccc(cc2C(=NCC1=O)c3ccccc3F)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 313.2838
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

3.92515191E11
PubMed

PubMed

TitleDatePubMed
Prolonged upper airway instability in the parenteral use of benzodiazepine with levomepromazine.
2000 Feb
Identification of amino acid residues responsible for the alpha5 subunit binding selectivity of L-655,708, a benzodiazepine binding site ligand at the GABA(A) receptor.
2001 Apr
Losigamone. Dr Willmar Schwabe.
2001 Dec
Density and distribution of hippocampal neurotransmitter receptors in autism: an autoradiographic study.
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
Radioligand binding assays in the drug discovery process: potential pitfalls of high throughput screenings.
2001 Feb
Heterogeneity of hippocampal GABA(A) receptors: regulation by corticosterone.
2001 Jan 1
[Plastic bag as the method in suicide and homicide].
2001 Jan-Feb
Honokiol and magnolol selectively interact with GABAA receptor subtypes in vitro.
2001 Jul
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
It's a rave new world: rave culture and illicit drug use in the young.
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
Behavioral effects of flunitrazepam: reinforcing and discriminative stimulus effects in rhesus monkeys and prevention of withdrawal signs in pentobarbital-dependent rats.
2001 Jun 1
Analytical methodology for the detection of benzodiazepine consumption in opioid-dependent subjects.
2001 Mar
[3H]Ro 15-1788 binding sites to brain membrane of the saltwater Mugil cephalus.
2001 Mar
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
Functional pharmacology of GABA(A) receptors containing the chicken brain gamma 4 subunit.
2001 May 4
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
[Clinical aspects of abuse drugs mainly used by adolescents].
2001 Oct
3H-nicotine, 3H-flunitrazepam, and 3H-cocaine incorporation into melanin: a model for the examination of drug-melanin interactions.
2001 Oct
Evidence for a role for GABA(A) and NMDA receptors in ethanol inhibition of long-term potentiation.
2001 Oct 19
Lack of allosteric modulation of striatal GABA(A) receptor binding and function after cocaine sensitization.
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
Sensitive method for the detection of 22 benzodiazepines by gas chromatography-ion trap tandem mass spectrometry.
2002 Apr 19
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
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
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
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
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

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 Fri Jun 25 20:51:08 UTC 2021
Edited
by admin
on Fri Jun 25 20:51:08 UTC 2021
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 [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
FLUNITRAZEPAM [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QN05CD03
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
DEA NO. 2763
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
NCI_THESAURUS C1012
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
WHO-ATC N05CD03
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
Code System Code Type Description
IUPHAR
4193
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
PRIMARY
FDA UNII
620X0222FQ
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
PRIMARY
MERCK INDEX
M5447
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PRIMARY Merck Index
ChEMBL
CHEMBL13280
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PRIMARY
DRUG CENTRAL
1202
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PRIMARY
CAS
1622-62-4
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PRIMARY
EPA CompTox
1622-62-4
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
PRIMARY
HSDB
6960
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
PRIMARY
PUBCHEM
3380
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PRIMARY
RXCUI
4460
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
FLUNITRAZEPAM
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
PRIMARY
INN
2951
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PRIMARY
DRUG BANK
DB01544
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PRIMARY
MESH
D005445
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PRIMARY
NCI_THESAURUS
C87672
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
PRIMARY
ECHA (EC/EINECS)
216-597-8
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
PRIMARY
EVMPD
SUB07710MIG
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
PRIMARY
LACTMED
Flunitrazepam
Created by admin on Fri Jun 25 20:51:08 UTC 2021 , Edited by admin on Fri Jun 25 20:51:08 UTC 2021
PRIMARY
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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
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