Secobarbital

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Secobarbital
Clinical data
Pregnancy
category
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability?
Protein binding45-60%[1]
MetabolismHepatic
Elimination half-life15-40 hours[1]
ExcretionRenal
Identifiers
  • 5-(1-methylbutyl)-5-prop-2-enyl-
    hexahydropyrimidine-2,4,6-trione
CAS Number
PubChem CID
DrugBank
CompTox Dashboard (EPA)
ECHA InfoCard100.000.894 Edit this at Wikidata
Chemical and physical data
FormulaC12H18N2O3
Molar mass238.283 g·mol−1

Secobarbital (marketed by Eli Lilly and Company under the brand name Seconal) is a barbiturate derivative drug. It possesses anaesthetic, anticonvulsant, sedative and hypnotic properties. In the United Kingdom, it was known as Quinalbarbitone.

Indications

Secobarbital is indicated for:

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

Availability

It is available as either 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

Recreational use

Secobarbital began to be widely abused 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, 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 but is now rarely prescribed due to problems with abuse and overdose.

Cause of death of Princess Leila Pahlavi

Princess Leila of Iran was found dead in her room in the Leonard Hotel in London, England [June 10, 2001], and was found to have more than five times the lethal dose of quinalbarbitone, a barbiturate, which is used to treat insomnia, in her system. Leila Pahlavi suffered from anorexia nervosa, chronic low self-esteem, and severe depression.

Cause of death of Charles Boyer

Two days after his wife died from cancer in 1978, Charles Boyer committed suicide with an overdose of Seconal.

Cause of death of Bartley Crum

Bartley Crum was the attorney for some of the so-called "Hollywood Ten" who were subpoenaed to appear before the House Un-American Activities Committee in 1947. The FBI tapped Crum's phones, opened his mail, and shadowed him constantly. Labeled as subversive, he ended up losing most of his clients and, unable to cope with stress from the harassment, committed suicide in 1959 by washing down an entire bottle of Seconal with whisky.

Cause of death of Judy Garland

Judy Garland, of "The Wizard of Oz" fame, 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]

Role in death of Jimi Hendrix

Secobarbital played a role in the September 18, 1970 death of legendary rock guitarist Jimi Hendrix, who purportedly took nine Vesperax tablets (a sleeping pill containing secobarbital, brallobarbital and hydroxyzine) after a night of drinking wine and was later found dead in his London apartment. Hendrix' death was caused by asphyxiation, after Hendrix presumably aspirated vomit in his sleep as a result of the mixture of the excessive barbiturate dose and alcohol.

Role in death of Anissa Jones

Anissa Jones' fatal overdose was of a combination of cocaine, PCP, Methaqualone, and Seconal. The San Diego County coroner said it was one of the most severe cases of drug overdose ever seen in San Diego County.

Role in death of Beverly Kenney

Jazz singer Beverly Kenney fatally overdosed on a combination of alcohol and Seconal on April 13, 1960.

Cause of death of Carol Landis

On July 5, 1948, Carole Landis committed suicide by taking an overdose of Seconal in her Brentwood Heights, California home.

Cause of death of Marilyn Monroe

In March 2007, a Los Angeles-based Australian writer and director named Philippe Mora uncovered previously-classified government documents regarding Marilyn Monroe's death. These documents, in turn, cited Seconal as Monroe's barbiturate of choice for her alleged suicide.

Cause of death of Alejandra Pizarnik

Alejandra Pizarnik, an Argentine poetess, reportedly died, in 1972 at the age of 36, from a self-induced overdose of seconal.

Cause of death of Lupe Velez

Lupe Velez, a Mexican actress who starred in many Hollywood films from 1927 to her death in 1944. On December 13, 1944 she committed suicide with an overdose of Seconal. She was 36 years old.

Use as a lethal injection

Secobarbital overdose was the most common method of implementing physician-assisted suicide (PAS) in Oregon until Eli Lilly and Company discontinued manufacturing it in May 2001, leading to a shortage of the drug. Since then, pentobarbital has dominated in Oregon PAS. Ranbaxy Laboratories Limited have experienced approval issues in their attempts to produce 100 mg secobarbital capsules, but there is no longer a shortage as of October 2006.

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

References

  1. ^ a b Lexi-Comp. "Secobarbital".
  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

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Secobarbital&oldid=230719778"