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P5178

Sigma-Aldrich

Phenobarbital sodium salt

Synonym(s):

5-Ethyl-5-phenyl-2,4,6-trioxohexahydropyrimidine sodium salt, 5-Ethyl-5-phenylbarbituric acid sodium salt, Luminal sodium salt, Sodium 5-ethyl-5-phenylbarbiturate

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About This Item

Empirical Formula (Hill Notation):
C12H11N2NaO3
CAS Number:
57-30-7
Molecular Weight:
254.22
Beilstein:
3802044
EC Number:
200-322-3
MDL number:
MFCD00036211
UNSPSC Code:
12352202
PubChem Substance ID:
24898608
NACRES:
NA.77

form

powder

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 IV (Portugal)

solubility

H2O: 1 g/mL
ethanol: 100 mg/mL

originator

Bayer

SMILES string

[Na+].CCC1(C(=O)NC([O-])=NC1=O)c2ccccc2

InChI

1S/C12H12N2O3.Na/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16;/h3-7H,2H2,1H3,(H2,13,14,15,16,17);/q;+1/p-1

InChI key

WRLGYAWRGXKSKG-UHFFFAOYSA-M

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Application

Phenobarbital sodium salt has been used:
  • to anesthetize mice for inducing ischemia-reperfusion injury
  • as a positive control for the activation of constitutive androstane receptor (CAR)
  • in bioluminescent yeast bioreporters (BLYAS) assay

Biochem/physiol Actions

Phenobarbital, a substituted barbituric acid is an antileptic drug and is not easily eliminated from circulation. It hyperpolarizes the synaptic neuronal membranes by favoring the activation of neuronal postsynaptic GABAA receptors by γ aminobutyric acid (GABA). Phenobarbital is also effective in treating neonatal seizures and status epilepticus.
Sedative; hypnotic; anticonvulsant; enhances GABAergic activity.

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 Dopamine and Norepinephrine Metabolism and GABAA Receptors pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H317,H351

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2 - Skin Sens. 1

Storage Class Code

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

WGK

WGK 3

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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Mohamed A Farag et al.
Molecules (Basel, Switzerland), 24(18) (2019-09-20)
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Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 42(6), 2492-2506 (2017-08-30)
Aberrant vascular smooth muscle cell (VSMC) proliferation and migration contribute to the development of vascular pathologies, such as atherosclerosis and post-angioplasty restenosis. The aim of this study was to determine whether miR-22-3p plays a role in regulating human artery vascular
Takafumi Yamaguchi et al.
The Journal of toxicological sciences, 44(7), 459-469 (2019-07-05)
Phenobarbital (PB) and Di (2-ethylhexyl) phthalate (DEHP), an anti-epileptic drug and a plasticizer used in flexible polyvinylchloride formulations, respectively, are well-known typical hepatotoxicants. This study investigated the effects of PB (100 mg/kg/day) or DEHP (500 mg/kg/day) on the endocrine system
Jie Meng et al.
Scientific reports, 3, 2655-2655 (2013-09-14)
A novel nanofibrous composite scaffold composed of super-paramagnetic γ-Fe2O3 nanoparticles (MNP), hydroxyapatite nanoparticles (nHA) and poly lactide acid (PLA) was prepared using electrospinning technique. The scaffold well responds extern static magnetic field with typical saturation magnetization value of 0.049 emu/g as
Di Zhao et al.
Innate immunity, 27(7-8), 533-542 (2021-11-19)
Crohn's disease activates the inflammatory reactions to induce intestinal disorders. Enteral nutrition (EN) could exert general immunomodulatory effects. Cecal ligation and perforation (CLP) surgery was utilized to establish Crohn's disease mice models. Survival analysis, hematoxylin-eosin staining, flow cytometry, ELISA, Western
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