Secobarbital

Source: Wikipedia, the free encyclopedia.
Secobarbital
Clinical data
Trade namesSeconal
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa682386
Pregnancy
category
  • D (United States)
QN51AA02 (WHO)
Legal status
Legal status
Renal
Identifiers
  • (RS)-5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
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) checkY
  • Key:KQPKPCNLIDLUMF-UHFFFAOYSA-N checkY
  (verify)

Secobarbital (as the

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 Secobarbital is considered to be an obsolete sedative-hypnotic (sleeping pill), and as a result, it has largely been replaced by the benzodiazepine family.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]

Indications

Secobarbital is indicated for:

  • Treatment of epilepsy
  • Temporary treatment of insomnia
  • Use as a preoperative medication to produce
    anxiolysis
    in short surgical, diagnostic, or therapeutic procedures which are minimally painful.

Availability

Secobarbital sodium, 100mg

hygroscopic
powder that is soluble in water and ethanol.

While generic versions of the drug were in existence after Eli Lilly's patent of the name Seconal expired, currently there are no companies that manufacture the drug generically in the United States. Until 2020, Valeant was the sole marketer of Seconal in the United States.[4] As of 2021, Valeant discontinued the product, and Bausch Health became the sole supplier of Seconal. Bausch Health stopped manufacturing the product in January 2022.[8]

Secobarbital sodium

The sodium salt of secobarbital is classified separately from the free acid, as follows:

  • CAS number: 309-43-3
  • Chemical formula: C12H18N2NaO3
  • Molecular weight: 260.265

Side effects

Possible side effects of secobarbital include:

  • Somnolence[9]
  • Impaired motor functions
  • Anxiety
  • Confusion
  • Agitation, irritability, or excitability
  • Headache[9]
  • Hunger
  • Nausea
  • Vomiting
  • Nightmares
  • Increased sensitivity to pain
  • Allergic reactions

Withdrawal

Secobarbital may produce psychological addiction and produces physical dependence if used for an extended period of time.[12] Withdrawal symptoms may occur if long-term use is abruptly ended and can include:

  • Anxiety
  • Insomnia
  • Lack of appetite
  • Seizures[13]
  • Tremors
  • Possible death as a result of withdrawal

Recreational and lethal use

Secobarbital was widely abused for recreational purposes in the 1960s, 1970s, and 1980s, and accidental overdose was associated with the drug. Lilly's Seconal came in a bright orange/red bullet shaped capsule known as a Pulvule. Prescription use of secobarbital decreased beginning in the early 1980s by which time

benzodiazepines had become increasingly common. Secobarbital has acquired many nicknames, the most common being "reds," "red devils," or "red dillies" (because of the color of the capsules). Other common nicknames are "seccies," "Cardinals," "ruby slippers," and, according to the Wegman's School of Pharmacy curriculum, "red hearts". A less common nickname is "dolls"; this was partly responsible for the title of Jacqueline Susann's novel Valley of the Dolls, whose main characters use secobarbital and other such drugs. Actresses Carole Landis, Judy Garland, playwright Tennessee Williams, and journalist Dorothy Kilgallen allegedly either died by suicide or of accidentally overdosing on secobarbital.[14] Seconal was used to induce Fred Hampton into docility before he was then killed in his bed in the early hours of December 4, 1969.[15]

In 1978, 1000 pills of Seconal were recovered in Jonestown, along with substantial quantities of Valium, Thorazine, Talwin, Demerol, and other sedatives, hypnotics, and analgesics.[16]

Use in animal and human euthanasia

In the

thiopental or 1 gram of propofol administered intravenously by a doctor, followed by a muscle relaxant.[17] In recent years only 15% of those who died by euthanasia opted for orally consuming the lethal drug(s), the rest choosing to have the drugs administered intravenously by a doctor instead.[18]

In the United States, secobarbital and pentobarbital are the most common drugs prescribed under

Ranbaxy Laboratories Limited
previously experienced various issues in their attempts to produce 100 mg secobarbital capsules.

In 2017, secobarbital was made available for physician-assisted suicide in Canada.[22]

It is a component in the

Somulose, used for euthanasia of horses and cattle
.

The LD50 of secobarbital has been reported to be between 125 mg/kg (rat, oral) and 267 mg/kg (mouse, oral).[23]

See also

References

  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. ^ a b 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.
  5. ^ "» Seconal Sodium®". Marathonpharma.com. 2013-07-31. Archived from the original on 2012-06-28. Retrieved 2014-03-05.
  6. ^ "Marathon Pharma to Focusing Exclusively on Rare Disease". Marathon Pharmaceuticals, LLC. Archived from the original on 2016-03-29. Retrieved 2016-03-24.
  7. ^ a b "Seconal Sodium - FDA prescribing information, side effects and uses". www.drugs.com. Archived from the original on 2016-04-07. Retrieved 2016-03-24.
  8. ^ "Drug Shortage Detail: Secobarbital Capsules".
  9. ^
    PMID 5338884
    .
  10. S2CID 37714069
    .
  11. PMID 5448377
    .
  12. PMID 13491317
    .
  13. S2CID 38785409
    .
  14. ^ "The dark side of Los Angeles: crime and corruption in Tinseltown – in pictures". The Guardian. 21 February 2018. Archived from the original on 24 April 2018 – via www.theguardian.com.
  15. OCLC 957772989.{{cite book}}: CS1 maint: location missing publisher (link
    )
  16. ^ King P (December 28, 1978). "How Jones Used Drugs". San Francisco Examiner.
  17. ^ unknown; et al. (July 29, 2010). "Hulp bij zelfdoding(Dutch)". Oncoline. Archived from the original on June 29, 2016.
  18. ^ Croonen H (April 1, 2010). "Euthanasiedrank verliest terrein(Dutch)". Medisch contact.
  19. S2CID 23013621
    .
  20. ^ "Oregon's Death with Dignity Act 2013 Report" (PDF). Oregon Health Authority. January 28, 2014. Archived (PDF) from the original on November 18, 2014.
  21. PMID 12621146
    .
  22. ^ Bryden J (November 17, 2017). "Newly Available Drug Secobarbital Could Boost Number of Self-Administered Assisted Deaths". CBC.
  23. ^ NIH. "Secobarbital - Human Health Effects". Archived from the original on 2018-02-22.

External links

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