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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.

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

1982
PubMed

PubMed

TitleDatePubMed
A puzzling case of seizures and visual hallucinations during clomipramine treatment with a high dose but causing a low serum concentration.
1999 May
Mimicking gene defects to treat drug dependence.
2000
Convulsive status epilepticus following abrupt high-dose benzodiazepine discontinuation.
2000 Apr 1
Neocortical hyperexcitability after GABA withdrawal in vitro.
2000 Mar
Semiautomated high-performance liquid chromatographic method for the determination of benzodiazepines in whole blood.
2001 Apr
Unsulfated and sulfated neurosteroids differentially modulate the binding characteristics of various radioligands of GABA(A) receptors following chronic ethanol administration.
2001 Apr
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
Nutmeg (myristicin) poisoning--report on a fatal case and a series of cases recorded by a poison information centre.
2001 Apr 15
[Clonidine combined with flunitrazepam before carotid endarterectomy decreases cerebrovascular CO2 reactivity].
2001 Aug
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
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
Synthesis and preliminary pharmacological evaluation of coumestans with different patterns of oxygenation.
2001 Feb 12
[Drugs and drug abusers].
2001 Feb 17
Evaluation of native GABA(A) receptors containing an alpha 5 subunit.
2001 Feb 9
Heterogeneity of hippocampal GABA(A) receptors: regulation by corticosterone.
2001 Jan 1
Drug-facilitated date rape.
2001 Jul 10
Olanzapine-induced retarded ejaculation: role of paroxetine comedication? A case report.
2001 Jul-Aug
Atrial flutter in fetuses and early childhood: a report of eight cases.
2001 Jun
Drug-facilitated sexual assault.
2001 Jun
It's a rave new world: rave culture and illicit drug use in the young.
2001 Jun
Allosteric modulation in spontaneously active mutant gamma-aminobutyric acidA receptors.
2001 Jun 1
Observation of psychoactive substance consumption: methods and results of the French OPPIDUM programme.
2001 Mar
Analytical methodology for the detection of benzodiazepine consumption in opioid-dependent subjects.
2001 Mar
Regional distribution of benzodiazepine binding sites in the human newborn and infant hypothalamus. A quantitative autoradiographic study.
2001 Mar 23
Synaptically released neurotransmitter fails to desensitize postsynaptic GABA(A) receptors in cerebellar cultures.
2001 May
Pharmacodynamic and receptor binding changes during chronic lorazepam administration.
2001 May-Jun
Modulation of rate of onset and intensity of drug effects reduces abuse potential in healthy males.
2001 Nov 1
Characterization of [3H]flunitrazepam binding to melanin.
2001 Nov 15
[Tetraplegia in the course of coma from drug intoxication].
2001 Oct
Mutagenesis of the GABA(A) receptor alpha1 subunit reveals a domain that affects sensitivity to GABA and benzodiazepine-site ligands.
2001 Oct
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
The flunitrazepam abuse prevention program at a general hospital in Taiwan: a descriptive study.
2002 Aug
[Acute ischemia of the leg in a drug addict].
2002 Feb
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
Citalopram in fatal poisoning cases.
2002 Mar 28
[Fatal outcome of poisoning with the benzodiazepines flunitrazepam and diazepam].
2002 Mar-Apr
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 Dec 15 15:05:22 GMT 2023
Edited
by admin
on Fri Dec 15 15:05:22 GMT 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 Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
DEA NO. 2763
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
NCI_THESAURUS C1012
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
WHO-ATC N05CD03
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
Code System Code Type Description
IUPHAR
4193
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
PRIMARY
FDA UNII
620X0222FQ
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
PRIMARY
MERCK INDEX
m5447
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
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
DTXSID7023065
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
PRIMARY
SMS_ID
100000092658
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
PRIMARY
CHEBI
31622
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PRIMARY
HSDB
6960
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PRIMARY
PUBCHEM
3380
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PRIMARY
RXCUI
4460
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
FLUNITRAZEPAM
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
PRIMARY
INN
2951
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PRIMARY
DRUG BANK
DB01544
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
PRIMARY
MESH
D005445
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
PRIMARY
NCI_THESAURUS
C87672
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
PRIMARY
ECHA (EC/EINECS)
216-597-8
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
PRIMARY
EVMPD
SUB07710MIG
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
PRIMARY
LACTMED
Flunitrazepam
Created by admin on Fri Dec 15 15:05:22 GMT 2023 , Edited by admin on Fri Dec 15 15:05:22 GMT 2023
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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