Secobarbital

Secobarbital (as the sodium salt, originally marketed by Eli Lilly and Company for the treatment of insomnia, and subsequently by other companies as described below, under the brand name Seconal) is a short-acting barbiturate derivative drug that was patented in 1934 in the United States. It possesses anaesthetic, anticonvulsant, anxiolytic, sedative, and hypnotic properties. In the United Kingdom, it was known as quinalbarbitone. It is the most frequently used drug in physician-assisted suicide within the United States. Secobarbital is considered to be an obsolete sedative-hypnotic (sleeping pill), and as a result, it has largely been replaced by the benzodiazepine family. Seconal was widely abused, known on the street as "red devils" or "reds".

Secobarbital
Clinical data
Trade namesSeconal
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa682386
Pregnancy
category
  • D (United States)
Routes of
administration
Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability?
Protein binding45-60%
MetabolismHepatic
Elimination half-life15-40 hours
ExcretionRenal
Identifiers
  • (RS)-5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.894
Chemical and physical data
FormulaC12H18N2O3
Molar mass238.287 g·mol−1
3D model (JSmol)
  • O=C1NC(NC(C1(CC=C)C(CCC)C)=O)=O
  • InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17) Y
  • Key:KQPKPCNLIDLUMF-UHFFFAOYSA-N Y
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