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F9261

Sigma-Aldrich

Flunitrazepam

Synonym(s):

5-(2-Fluorophenyl)-1-methyl-7-nitro-3H-1,4-benzodiazepin-2(1H)-one, Ro 5-4200

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About This Item

Empirical Formula (Hill Notation):
C16H12FN3O3
CAS Number:
1622-62-4
Molecular Weight:
313.28
EC Number:
216-597-8
MDL number:
MFCD00057906
UNSPSC Code:
12352200
PubChem Substance ID:
24894993
NACRES:
NA.77

drug control

USDEA Schedule IV; Home Office Schedule 3; psychotrope (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IIC (Portugal)

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1 mg/mL
DMF: soluble
ethanol: soluble

originator

Roche

SMILES string

CN1C(=O)CN=C(c2ccccc2F)c3cc(ccc13)[N+]([O-])=O

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

InChI key

PPTYJKAXVCCBDU-UHFFFAOYSA-N

Gene Information

human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562) , GABRD(2563) , GABRE(2564) , GABRG1(2565) , GABRG2(2566) , GABRG3(2567) , GABRP(2568) , GABRQ(55879)
rat ... Gabra2(29706)

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Biochem/physiol Actions

Hypnotic; anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GABAA Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H336,H412

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R M McKernan et al.
Molecular pharmacology, 54(1), 33-43 (1998-07-11)
Photoincorporation of ligands into the benzodiazepine site of native gamma-aminobutyric acidA (GABAA) receptors provides useful information about the nature of the benzodiazepine (BZ) binding site. Photoincorporation of flunitrazepam into a single population of GABAA receptors, recombinant human alpha1beta3gamma2, was investigated
Danni Harris et al.
Journal of medicinal chemistry, 51(13), 3788-3803 (2008-06-10)
Ligands that bind to the benzodiazepine binding site on the GABA A receptor can attenuate or potentiate cognition. To investigate this property, the chemical determinants favoring selective binding or selective activation of the alpha5beta2gamma2 and alpha1beta2gamma2 GABA A receptor isoforms
Virpi Laukkanen et al.
Alcohol (Fayetteville, N.Y.), 47(2), 103-108 (2013-01-22)
Ethanol modulates the GABA(A) receptor to cause sedative, anxiolytic and hypnotic effects that are qualitatively similar to benzodiazepines and barbiturates. The aim of this study was to explore if GABA(A) receptor density is altered in post-mortem brains of anxiety-prone Cloninger
Mari Takeuchi et al.
Annals of surgical oncology, 19(12), 3963-3970 (2012-06-16)
Postoperative delirium is a common complication after major surgery and is characterized by acute confusion with fluctuating consciousness. The aim of this study was to investigate the incidence and risk factors of postoperative delirium in patients with esophageal cancer. We
Shiuan-Woei LinWu et al.
Biochemical pharmacology, 83(12), 1690-1699 (2012-03-27)
Nitrobenzodiazepine (NBDZ) is an addictive drug of the abused substances that causes severe neurological effects and even death. Bacterial type I nitroreductase NfsB (EC 1.5.1.34) has been reported to catalyze NBDZ into inactive metabolite 7-amino-benzodiazepine (7ABDZ) with promising activity, so
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