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Merck

D0899

Diazepam

≥98% (TLC), powder, GABAA receptor ligand

Synonym(s):

7-Chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2(1H)-one, Ro 5-2807

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About This Item

Empirical Formula (Hill Notation):
C16H13ClN2O
CAS Number:
439-14-5
Molecular Weight:
284.74
NACRES:
NA.77
PubChem Substance ID:
24893306
UNSPSC Code:
12352200
EC Number:
207-122-5
MDL number:
MFCD00057323

Product Name

Diazepam,

InChI

1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3

InChI key

AAOVKJBEBIDNHE-UHFFFAOYSA-N

SMILES string

CN1C(=O)CN=C(c2ccccc2)c3cc(Cl)ccc13

form

powder

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); 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 ... Gabra1(29705), Gabra2(29706)

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.6 mg/mL
DMF: soluble
H2O: slightly soluble
ethanol: soluble

originator

Roche

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Application

Diazepam has been used:
  • as an anxiolyte in pilocarpine protocol.
  • in multi-electrode array (MEA) technology
  • as a marker for human serum albumin

Biochem/physiol Actions

Anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.
Diazepam is a benzodiazepine anxiolytic agent. It serves as a prototype ligand for the GABAA receptor benzodiazepine modulatory site.
Diazepam is often used as a sedative. Its metabolism involves cytochrome P450 (CYP) 2C19 and 3A4. Diazepam has immediate action upon administration.

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

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000452482
0000452482
0000319655
0000319654
059H0821

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Anna D Manis et al.
JCI insight, 6(1) (2020-11-25)
Kir5.1 is an inwardly rectifying potassium (Kir) channel subunit abundantly expressed in the kidney and brain. We previously established the physiologic consequences of a Kcnj16 (gene encoding Kir5.1) knockout in the Dahl salt-sensitive rat (SSKcnj16-/-), which caused electrolyte/pH dysregulation and
Drain's PeriAnesthesia Nursing - E-Book: A Critical Care Approach, 270-270 (2012)
CYP2C19 genotype affects diazepam pharmacokinetics and emergence from general anesthesia.
Inomata S, et al.
Clinical Pharmacology and Therapeutics, 78(6), 647-655 (2005)
Barbara Taferner et al.
Journal of medicinal chemistry, 54(15), 5349-5361 (2011-06-28)
A series of 31 analogues of the neolignan honokiol (a major constituent of Magnolia officinalis) was synthesized, and their effects on GABA(A) receptors expressed in Xenopus oocytes were investigated. Honokiol enhanced chloride currents (I(GABA)) through GABA(A) receptors of seven different
FDG-PET and NeuN-GFAP immunohistochemistry of hippocampus at different phases of the pilocarpine model of temporal lobe epilepsy
Zhang L, et al.
International Journal of Medical Sciences, 12(3), 288-288 (2015)
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