Structure via PubChem · Public domain (PubChem)
secobarbital
Sign in to saveAlso known as 5-(1-methylbutyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione, 5-allyl-5-(1-methylbutyl)barbituric acid, 5-allyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione, 5-allyl-5-(1-methylbutyl)pyrimidine-2,4,6(1H,3H,5H)-trione, quinalbarbitone, (+-)-secobarbital, secobarbitone, (±)-secobarbital
Secobarbital, sold under the brand name Seconal among others, is a short-acting barbiturate drug originally used for the treatment of insomnia. It was patented by Eli Lilly and Company in 1934 in the United States. It possesses anesthetic, anticonvulsant, anxiolytic, sedative, and hypnotic properties. In the United Kingdom, it was known as quinalbarbitone. Secobarbital is considered to be an obsolete sedative-hypnotic (sleeping pill) and has largely been replaced by the benzodiazepine family. It was widely abused, known on the street as "red devils" or "reds." Among barbiturates, secobarbital
Key facts
- Drug.N
- 2
- Drug.O
- 3
- Drug.Watchedfields
- changed
- Drug.class
- Barbiturate
- Drug.verifiedrevid
- 458777042
- Drug.IUPAC_name
- (RS)-5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
- Drug.image
- Secobarbital.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 150
- Drug.image2
- Secobarbital 3D xtal ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 210
- Drug.tradename
- Seconal, others
- Drug.MedlinePlus
- a682386
- Drug.pregnancy_category
- D (United States)
- Drug.legal_BR
- B1
- Drug.legal_CA
- Schedule IV
- Drug.legal_DE
- Anlage III
via Wikipedia infobox
Chemical data
- Formula
- C12H18N2O3
- Molecular weight
- 238.28 g/mol
- IUPAC name
- 5-pentan-2-yl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
- SMILES
- CCCC(C)C1(C(=O)NC(=O)NC1=O)CC=C
- InChIKey
- KQPKPCNLIDLUMF-UHFFFAOYSA-N
- XLogP
- 2
- Polar surface area
- 75.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
894 papers- Secobarbital burns.A.M.A. archives of otolaryngology · 1953
- Interaction of secobarbital with warfarin pseudoracemates.Clinical pharmacology and therapeutics · 1980
- Intra-arterial secobarbital.The New England journal of medicine · 1973
- Effects of marihuana combined with secobarbital.Clinical pharmacology and therapeutics · 1975
- Influence of cannabidiol on secobarbital effects and plasma kinetics.Clinical pharmacology and therapeutics · 1976
via PubMed
Wikidata facts
- Mass
- 238.132
Show 5 more facts
- defined daily dose
- 0.1
- chemical formula
- C₁₂H₁₈N₂O₃
- canonical SMILES
- CCCC(C)C1(C(=O)NC(=O)NC1=O)CC=C
- World Health Organisation international non-proprietary name
- secobarbital
- Commons category
- Secobarbital
via Wikidata · CC0
~7 min read
Article
11 sectionsContents
- Uses
- Medical
- Recreational and lethal use
- Assisted dying
- Adverse effects
- Withdrawal
- Availability
- Secobarbital sodium
- See also
- References
- External links
Secobarbital, sold under the brand name Seconal among others, is a short-acting barbiturate drug originally used for the treatment of insomnia. It was patented by Eli Lilly and Company in 1934 in the United States. It possesses anesthetic, anticonvulsant, anxiolytic, sedative, and hypnotic properties. In the United Kingdom, it was known as quinalbarbitone. Secobarbital is considered to be an obsolete sedative-hypnotic (sleeping pill) and has largely been replaced by the benzodiazepine family. It was widely abused, known on the street as "red devils" or "reds." Among barbiturates, secobarbital carries a particularly high risk of abuse and addiction, which is largely responsible for it falling out of use.
==Uses== ===Medical=== Secobarbital is used for managing symptoms of epilepsy and for short-term treatment of insomnia. It is also used as a preoperative medication to produce anesthesia and anxiolysis for short surgical, diagnostic, or therapeutic procedures which are minimally painful.