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=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
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 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11393809 \| https://www.ncbi.nlm.nih.gov/pubmed/9914279	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

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108 Sources: http://www.medicines.ie/printfriendlydocument.aspx?documentid=1048&companyid=264	Primary		Approved 8429	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

Title	Date	PubMed
Mimicking gene defects to treat drug dependence.	2000	10911933
Synergistic protection of allopregnanolone and phenobarbital against maximal electroshock seizures in mice.	2001 Apr	11742590
Unsulfated and sulfated neurosteroids differentially modulate the binding characteristics of various radioligands of GABA(A) receptors following chronic ethanol administration.	2001 Apr	11311894
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
Simultaneous determination of fifteen low-dosed benzodiazepines in human urine by solid-phase extraction and gas chromatography-mass spectrometry.	2001 Dec 25	11767312
[Drugs and drug abusers].	2001 Feb 17	11252979
Drug-facilitated date rape.	2001 Jul 10	11468961
Atrial flutter in fetuses and early childhood: a report of eight cases.	2001 Jun	11529363
Designer drugs. Assess & manage patients intoxicated with ecstasy, GHB or rohypnol--the three most commonly abused designer drugs.	2001 Jun	11409205
It's a rave new world: rave culture and illicit drug use in the young.	2001 Jun	11405616
The association between intravenous haloperidol and prolonged QT interval.	2001 Jun	11386487
GABA(A) receptor gene expression in rat cortex: differential effects of two chronic diazepam treatment regimes.	2001 Jun 15	11398186
[3H]Ro 15-1788 binding sites to brain membrane of the saltwater Mugil cephalus.	2001 Mar	11255103
[3H]Flunitrazepam binding to recombinant alpha1beta2gamma2S GABAA receptors stably expressed in HEK 293 cells.	2001 May	11393809
Synaptically released neurotransmitter fails to desensitize postsynaptic GABA(A) receptors in cerebellar cultures.	2001 May	11353001
Pharmacodynamic and receptor binding changes during chronic lorazepam administration.	2001 May-Jun	11420062
3Alpha-hydroxy-5alpha-pregnan-20-one levels and GABA(A) receptor-mediated 36Cl(-) flux across development in rat cerebral cortex.	2001 Nov 26	11718833
3H-nicotine, 3H-flunitrazepam, and 3H-cocaine incorporation into melanin: a model for the examination of drug-melanin interactions.	2001 Oct	11599608
Lack of allosteric modulation of striatal GABA(A) receptor binding and function after cocaine sensitization.	2001 Sep	11566142
[Crime under the influence of psychoactive drugs: the problem of the duration of detection].	2002	11974439
Acrylamide disturbs the subcellular distribution of GABAA receptor in brain neurons.	2002	11967996
[Acute ischemia of the leg in a drug addict].	2002 Feb	11951700
Gamma-aminobutyric acidA and benzodiazepine receptor alterations in the rat brain after unilateral 6-hydroxydopamine lesions of the medial forebrain bundle.	2002 Jan	11783749
Psychological stress, but not physical stress, causes increase in diazepam binding inhibitor (DBI) mRNA expression in mouse brains.	2002 Jul 15	12117556
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
Citalopram in fatal poisoning cases.	2002 Mar 28	11955823
Tolterodine-associated acute mixed liver injury.	2002 May	11978158

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 `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

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Name

Type

Language

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

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