Structure via PubChem · Public domain (PubChem)
barbital
Sign in to saveAlso known as C₈H₁₂N₂O₃, Barbitone, DEBA, Veronal, 2,4,6(1H,3H,5H)-pyrimidinetrione, 5,5-diethylbarbituric acid, diethylmalonyl urea
Barbital (or barbitone), sold under the brand names Veronal for the pure acid and Medinal for the sodium salt, was the first commercially available barbiturate. It was used as a sleeping aid (hypnotic) from 1903 until the mid-1950s. The chemical names for barbital are diethylmalonyl urea or diethylbarbituric acid; hence, the sodium salt is known also as sodium diethylbarbiturate.
In the Vinony graph
Vinony's link graph records 684 inbound references to barbital, and connects out to benzodiazepine drug, allopregnanolone and isovaleric acid.
It is catalogued under topics including Barbiturates and ECHA InfoCard ID from Wikidata.
Vinony links it to 28 Wikipedia language editions.
Key facts
- Drug.verifiedrevid
- 443412703
- Drug.class
- Barbiturate
- Drug.IUPAC_name
- 5,5-diethylpyrimidine-2,4,6(1H,3H,5H)-trione
- Drug.image
- Barbital.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 120
- Drug.image2
- Barbital ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Veronal, Medinal
- Drug.MedlinePlus
- a682221
- Drug.legal_BR
- B1
- Drug.legal_CA
- Schedule IV
- Drug.legal_US
- Schedule IV
- Drug.legal_DE
- Anlage III
- Drug.routes_of_administration
- By mouth
- Drug.elimination_half life
- 30.3 (± 3.2) hours
- Drug.CAS_number
- 57-44-3
- Drug.ATC_prefix
- N05
via Wikipedia infobox
Chemical data
- Formula
- C8H12N2O3
- Molecular weight
- 184.19 g/mol
- IUPAC name
- 5,5-diethyl-1,3-diazinane-2,4,6-trione
- SMILES
- CCC1(C(=O)NC(=O)NC1=O)CC
- InChIKey
- FTOAOBMCPZCFFF-UHFFFAOYSA-N
- XLogP
- 0.6
- Polar surface area
- 75.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,965 papers- Barbital overdose and abuse.American journal of clinical pathology · 1975
- Continuous administration of barbital by pellet implantation.Journal of pharmacological methods · 1980
- Barbiturates.Oral surgery, oral medicine, and oral pathology · 1949
- AMOBARBITAL.Bulletin. American Pharmaceutical Association. Committee on National Formulary · 1949
- Delirium tremens: a double-blind comparison of diazepam and barbital treatment.Acta psychiatrica Scandinavica · 1978
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Named after
- Verona
- Mass
- 184.084792
Show 4 more facts
- chemical formula
- C₈H₁₂N₂O₃
- canonical SMILES
- CCC1(C(=O)NC(=O)NC1=O)CC
- Commons category
- Barbital
- has characteristic
- bitterness
via Wikidata · CC0
~5 min read
Encyclopedic overview
8 sectionsContents
- Synthesis
- Marketing
- Pharmacology
- pH buffer
- Poisoning
- In fiction
- References
- Further reading
Barbital (or barbitone), sold under the brand names Veronal for the pure acid and Medinal for the sodium salt, was the first commercially available barbiturate. It was used as a sleeping aid (hypnotic) from 1903 until the mid-1950s. The chemical names for barbital are diethylmalonyl urea or diethylbarbituric acid; hence, the sodium salt is known also as sodium diethylbarbiturate.
==Synthesis== Barbital, then called "Veronal", was first synthesized in 1902 by German chemists Emil Fischer and Joseph von Mering, who published their discovery in 1903. Barbital was prepared by condensing diethylmalonic ester with urea in the presence of sodium ethoxide, or by adding at least two molar equivalents of ethyl iodide to the silver salt of malonylurea (barbituric acid) or possibly to a basic solution of the acid. The result was an odorless, slightly bitter, white crystalline powder.
Excerpted from Wikipedia’s “barbital” article, available under the CC BY-SA 4.0 licence.