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F103

Sigma-Aldrich

Flurazepam dihydrochloride

solid

Synonym(s):

7-Chloro-1-(diethylamino)ethyl-5-(2-fluorophenyl)-3H-1,4-benzodiazepin-2(1H)-one dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C21H23ClFN3O · 2HCl
CAS Number:
1172-18-5
Molecular Weight:
460.80
EC Number:
214-630-0
MDL number:
MFCD00058189
UNSPSC Code:
12352100
PubChem Substance ID:
24894741
Pricing and availability is not currently available.

form

solid

drug control

USDEA Schedule IV; Home Office Schedule 4.1; psychotrope (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IV (Portugal)

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

color

light yellow

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: <6 mg/mL
H2O: slightly soluble

format

neat

SMILES string

Cl[H].Cl[H].CCN(CC)CCN1C(=O)CN=C(c2ccccc2F)c3cc(Cl)ccc13

InChI

1S/C21H23ClFN3O.2ClH/c1-3-25(4-2)11-12-26-19-10-9-15(22)13-17(19)21(24-14-20(26)27)16-7-5-6-8-18(16)23;;/h5-10,13H,3-4,11-12,14H2,1-2H3;2*1H

InChI key

ZIIJJOPLRSCQNX-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)

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Anxiolytic; anticonvulsant; GABAA receptor benzodiazepine modulatory site ligand.
Benzodiazepine anxiolytic; anticonvulsant; ligand for the GABAA receptor benzodiazepine modulatory site.

Caution

Photosensitive

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H373

Hazard Classifications

Acute Tox. 4 Oral - STOT RE 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
041K1105
SLBG2349V
059H0825

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Stephen I Deutsch et al.
European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology, 19(6), 398-401 (2009-02-05)
Stress induces changes in the endogenous tone of both GABA and NMDA receptor-mediated neurotransmission in the intact mouse. Because changes are observed 24 h after stress, epigenetically-regulated alterations in gene expression may mediate these effects. In earlier work, sodium butyrate
Guofu Shen et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 35(9), 1897-1909 (2010-05-07)
Benzodiazepine withdrawal anxiety is associated with potentiation of alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate receptor (AMPAR) currents in hippocampal CA1 pyramidal neurons attributable to increased synaptic incorporation of GluA1-containing AMPARs. The contribution of calcium/calmodulin-dependent protein kinase II (CaMKII) to enhanced glutamatergic synaptic strength during withdrawal
Marie-Pierre Sylvestre et al.
Statistics in medicine, 28(27), 3437-3453 (2009-08-27)
Many epidemiological studies assess the effects of time-dependent exposures, where both the exposure status and its intensity vary over time. One example that attracts public attention concerns pharmacoepidemiological studies of the adverse effects of medications. The analysis of such studies
K Xiang et al.
Neuroscience, 157(1), 153-163 (2008-09-23)
One week oral flurazepam (FZP) administration in rats results in reduced GABA(A) receptor-mediated synaptic transmission in CA1 pyramidal neurons associated with benzodiazepine tolerance in vivo and in vitro. Since voltage-gated calcium channel (VGCC) current density is enhanced twofold during chronic
M Dao Duong Thi et al.
The Journal of pharmacy and pharmacology, 61(3), 399-406 (2009-02-19)
To measure the metabolism and toxicity of 7-chloro-4-(cyclohexylmethyl)-1-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (BNZ-1) and 4-cyclohexylmethyl-1-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (BNZ-2), two new benzodiazepine analogues found to be effective against Leishmania amastigotes in vitro. The metabolism of BNZ-1 and -2 was investigated in isolated rat hepatocytes and rat liver
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