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Merck
CN

P5178

Phenobarbital sodium salt

GABAA receptor activator, powder

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
NACRES:
NA.77
PubChem Substance ID:
24898608
UNSPSC Code:
12352202
EC Number:
200-322-3
MDL number:
MFCD00036211
Beilstein/REAXYS Number:
3802044

Key Documents

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Product Name

Phenobarbital sodium salt,

InChI key

WRLGYAWRGXKSKG-UHFFFAOYSA-M

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

SMILES string

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

form

powder

Quality Level

200

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

solubility

H2O: 1 g/mL
ethanol: 100 mg/mL

originator

Bayer

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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.

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 crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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

Lot/Batch Number
0000477396
0000477396
0000469698
0000469698
0000454058

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Effective, easy to use and affordable?the discovery and use of phenobarbital
Bryan J
Pharmaceut. Res., 289(7728), 443-443 (2012)
Shui-Chuan Huang et al.
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
P R Territo et al.
Journal of veterinary pharmacology and therapeutics, 30(6), 508-515 (2007-11-10)
The development and validation of the maximal electro-shock (MES) model using phenobarbital (Pb) as the positive control is described. This approach builds on previous work in rodent model systems, and has been adapted to dogs as a tool for pharmaceutical
Liana M Yates et al.
Frontiers in veterinary science, 7, 86-86 (2020-03-11)
Phenobarbital is a common drug used to manage epilepsy in goats. However, the recommended dose and dosing frequency are based on studies in dogs and horses. Studies describing the pharmacokinetics of phenobarbital when administered orally and assessing changes in behavior
Tisp40 deficiency attenuates renal ischemia reperfusion injury induced apoptosis of tubular epithelial cells
Qin C, et al.
Experimental Cell Research, 359(1), 138 -1144 (2017)
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