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Merck
CN

F9261

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
NACRES:
NA.77
PubChem Substance ID:
24894993
UNSPSC Code:
12352200
EC Number:
216-597-8
MDL number:
MFCD00057906

Key Documents

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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

SMILES string

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

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); Pszichotróp anyag / Psychotropic Substance (Hungary), 78/2022. (XII. 28.) BM rendelet, kontrollierte Droge in Deutschland

Quality Level

200

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)

solubility

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

originator

Roche

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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.

Legal Information

German
Dieses Produkt fällt unter das Betäubungsmittelgesetz (BtMG). Für eine Bestellung dieses Produktes ist eine Erlaubnis nach § 3 BtMG zwingend erforderlich, es sei denn, es greift eine Ausnahme von der Erlaubnispflicht nach § 4 oder § 26 BtMG.

English
This product is subject to the German Narcotics Act. A permit under Section 3 of the German Narcotics Act is mandatory for ordering this product unless an exemption from the permit requirement under Section 4 or Section 26 of the German Narcotics Act applies.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Central nervous system

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

监管及禁止进口产品
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Certificates of Analysis (COA)

Lot/Batch Number
056F0685

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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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