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Secobarbital
Systematic (IUPAC) name
5-[(2R)-pentan-2-yl]-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
Identifiers
CAS number 76-73-3
ATC code N05CA06 QN51AA02
PubChem 5193
DrugBank APRD00497
ChemSpider 5005
Chemical data
Formula C12H18N2O3 
Mol. mass 238.283
Pharmacokinetic data
Bioavailability  ?
Protein binding 45-60%[1]
Metabolism Hepatic
Half life 15-40 hours[1]
Excretion Renal
Therapeutic considerations
Pregnancy cat. D (USA)
Legal status Schedule II (US)
Routes Oral
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Secobarbital Sodium (marketed by Eli Lilly and Company, and subsequently by other companies as described below, under the brand name Seconal) is a barbiturate derivative drug that was first synthesized in 1928. It possesses anaesthetic, anticonvulsant, sedative and hypnotic properties. In the United Kingdom, it was known as Quinalbarbitone.

Contents

Indications

Secobarbital is indicated for:

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

Availability

Secobarbital DOJ.jpg

Ranbaxy Pharmaceuticals, an India-based company now predominantly owned by the Japanese company Daiichi Sankyo, obtained the rights to market Seconal from Eli Lilly in 1998 and did so until September 18, 2008. The rights to market Seconal were then sold to Marathon Pharmaceuticals (http://marathonpharma.com), the current marketer. Seconal returned to the market in January 2009.[citation needed] It is available as 100 mg. capsules, either as a free acid or a sodium salt. The free acid is a white amorphous powder that is slightly soluble in water and very soluble in ethanol. The salt is a white hygroscopic powder that is soluble in water and ethanol.

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:

Withdrawal

Secobarbital is a fairly addictive drug, and withdrawal symptoms can occur if long-term usage is abruptly ended. Withdrawal symptoms can include:

  • Anxiety
  • Insomnia
  • Lack of appetite
  • Seizures
  • Tremors
  • Death as a result of withdrawl

Recreational use

Secobarbital began to be widely misused in the 1960s and 1970s, although with the advent of benzodiazepines, they have become less commonly used. Secobarbital has acquired many nicknames, the most common being reds, "red devils", or "red dillies" (it was originally packaged in red capsules). Another common nickname is "seccies". Another common nickname is "red hearts" according to the Wegman's School of Pharmacy curriculum. 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. Another popular brand of barbiturate pill Tuinal contained a combination of secobarbital and amobarbital. Tuinal, also previously an Eli Lilly product, has not been manufactured by any company with rights to market the drug in the United States since 1998. However, as of January 30, 2009, Marathon Pharmaceuticals also began marketing Amytal (amobarbital sodium) in single-unit packaging. If a person were prescribed Seconal, and also given Amytal, the person would be taking the generic equivalent of Tuinal, provided the Seconal and Amytal were taken at the same time and in equal quantities.

Famous deaths related to use

  • Judy Garland was found dead in her bathroom by her husband Mickey Deans on June 22, 1969. The stated exact cause of death by coroner Gavin Thursdon was accidental overdose of barbiturates; her blood contained the equivalent of 10 Seconal 100 mg capsules.[2]
  • Jimi Hendrix (musician), musician and vocalist died while at girlfriend's Monika Dannemann hotel room in London. It is uncertain how he died, but the coroner said that he had taken at least nine of his girlfriend's pills. He died September 18, 1970.
  • Beverly Kenney (January 29, 1932, Harrison, New Jersey - April 13, 1960, New York City) was an American jazz singer. Kenney committed suicide through a combination of alcohol and Seconal. She was 28.
  • Carole Landis was a popular actress of the 1940s who committed suicide on an overdose of Seconal in her Brentwood Heights, California home on July 5, 1948. She was 29 years old.
  • Tennessee Williams was reported to have died of "Acute Seconal Intolerance" at the Hotel Elysee in New York City in 1983. Reports at the time indicated he had choked on a bottle cap however later reports indicated the seconal connection.[3]
  • Alan Wilson, vocalist and founding member of Canned Heat, was found dead at age 27 in 1970, from a self-induced overdose of seconal. [4]

Use in physician-assisted suicide

Secobarbital overdose was the most common method of implementing physician assisted suicide in Oregon for many years. Subsequently, pentobarbital has dominated in Oregon PAD. Ranbaxy Laboratories Limited previously experienced various issues in their attempts to produce 100 mg secobarbital capsules. Currently, Marathon Pharmaceuticals is the sole marketer of the drug in the United States, although the drug remains manufactured by Ohm Laboratories.

It is a component in the veterinary drug Somulose, used for euthanasia of horses and cattle.

References

  1. ^ a b Lexi-Comp. "Secobarbital". http://www.merck.com/mmpe/lexicomp/secobarbital.html. 
  2. ^ Thomson, David,Film Studies: She couldn't act for toffee - until she burst into song; The Independent; 2004-06-27; Retrieved on 2007-01-26
  3. ^ Tennessee Williams' death myth - New York Post - February 15, 2010
  4. ^ De la Parra, Adolfo "Fito" (2000). Living the Blues: Canned Heat's Story of Music, Drugs, Death, Sex and Survival. Canned Heat Music. ISBN 0967644909. 

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