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Secobarbital information


Secobarbital
Clinical data
Trade namesSeconal
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa682386
Pregnancy
category
  • D (United States)
Routes of
administration
Oral
ATC code
  • N05CA06 (WHO) QN51AA02 (WHO)
Legal status
Legal status
  • BR: Class B1 (Psychoactive drugs)[1]
  • CA: Schedule IV
  • DE: Anlage III (Special prescription form required)
  • UK: Class B
  • US: Schedule II except when combined in a dosage unit with another active drug (in which case Schedule III)
  • UN: Psychotropic Schedule II
Pharmacokinetic data
Bioavailability?
Protein binding45-60%[2]
MetabolismHepatic
Elimination half-life15-40 hours[2]
ExcretionRenal
Identifiers
IUPAC name
  • (RS)-5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
CAS Number
  • 76-73-3 checkY
PubChem CID
  • 5193
IUPHAR/BPS
  • 7615
DrugBank
  • DB00418 checkY
ChemSpider
  • 5005 checkY
UNII
  • 1P7H87IN75
KEGG
  • D00430 checkY
ChEBI
  • CHEBI:9073 checkY
ChEMBL
  • ChEMBL447 checkY
CompTox Dashboard (EPA)
  • DTXSID6044145 Edit this at Wikidata
ECHA InfoCard100.000.894 Edit this at Wikidata
Chemical and physical data
FormulaC12H18N2O3
Molar mass238.287 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C1NC(NC(C1(CC=C)C(CCC)C)=O)=O
InChI
  • 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) checkY
  • Key:KQPKPCNLIDLUMF-UHFFFAOYSA-N checkY
  (verify)

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.[3] 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 Secobarbital is considered to be an obsolete sedative-hypnotic (sleeping pill), and as a result, it has largely been replaced by the benzodiazepine family.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".[4] Among the barbiturates, secobarbital carries a particularly high risk of abuse and addiction, largely responsible for its falling out of use.

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ a b Lexi-Comp. "Secobarbital". Archived from the original on 2007-12-02.
  3. ^ US patent 1954429, Shonle HA, "Propyl-Methyl Carbinyl Allyl Barbituric Acid and its Salts", issued 1934-04-10, assigned to Eli Lilly 
  4. ^ Dembosky A (23 March 2016). "Drug Company Jacks Up Cost Of Aid-In-Dying Medication". NPR. Archived from the original on 2016-03-23. Retrieved 2016-03-24.

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of a discontinued combination drug composed of two barbiturate salts (secobarbital sodium and amobarbital sodium) in equal proportions. Tuinal was introduced...

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Eli Lilly and Company

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manufactured Secobarbital, a barbiturate derivative with anaesthetic, anticonvulsant, sedative and hypnotic properties. Lilly marketed Secobarbital under the...

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Amobarbital

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as well as Tuinal, a combination drug containing equal quantities of secobarbital and amobarbital, were both manufactured by Eli Lilly until the late-1990s...

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Brallobarbital

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as part of a combination product called Vesparax, composed of 150 mg secobarbital, 50 mg brallobarbital and 50 mg hydroxyzine. The long half-life of this...

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Schedule X

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Methylphenidate Methylphenobarbital Pentobarbital Phencyclidine Phenmetrazine Secobarbital Preparations containing the above substances are also covered by this...

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Mebutamate

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comparable to those of barbiturates such as secobarbital, but is only around 1/3 the potency of secobarbital as a sedative. Side effects include dizziness...

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Thiamylal

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effects from other anaesthetics. It is the thiobarbiturate analogue of secobarbital. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes...

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Pentobarbital

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Australian Broadcasting Corporation. Retrieved 22 September 2021. Both secobarbital capsules and pentobarbital (usually known as the brand name, Nembutal)...

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Somnolence

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nitrazepam (Mogadon) and the barbiturates, such as amobarbital (Amytal) or secobarbital (Seconal) Other agents impacting the central nervous system in sufficient...

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used compared to better known barbiturates such as phenobarbital and secobarbital, although it saw more use in some European countries such as Bulgaria...

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September 25, 1972, she died by suicide after ingesting an overdose of secobarbital. Her work has influenced generations of authors in Latin America. Flora...

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Sodium salts

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Sedative

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Trazodone

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Sodium thiopental

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Chlordiazepoxide

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Reds

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(film), a 1981 American film starring and directed by Warren Beatty Secobarbital, a barbiturate derivative drug Red Arrows or The Reds, the Royal Air...

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the scene at age 39. An autopsy later showed a lethal combination of secobarbital and amobarbital, prescriptions for her insomnia and diet, which contributed...

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Methaqualone

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Cannabis

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Butabarbital

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of action gives butabarbital an abuse potential slightly lower than secobarbital. Butabarbital can be hydrolyzed to valnoctamide. Butabarbital is also...

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