Secobarbital

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Secobarbital

Systematic (IUPAC) name
5-(1-methylbutyl)-5-prop-2-enyl- hexahydropyrimidine-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 (marketed by Eli Lilly and Company 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 1 Indications 2 Availability 2.1 Secobarbital sodium 3 Side effects 4 Withdrawal 5 Recreational use 5.1 Cause of death of Judy Garland 5.2 Cause of death of Alan Wilson 5.3 Cause of Death of Jimi Hendrix 5.4 Cause of Death of Beverley Kenney 5.5 Cause of Death of Carole Landis 6 Use as a lethal injection 7 References 8 External links

[edit] Indications

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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.

[edit] Availability

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Ranbaxy Pharmaceuticals obtained marketing rights to Seconal from Eli Lilly in 1998 and marketed Seconal until September 18, 2008. The rights to Seconal were sold to Marathon Pharmaceuticals (http://marathonpharma.com). Seconal returned to the market last January 2009. It is available as 100 mg capsules. The new NDC number for ordering is: 42998-679-01 Seconal is primarily distributed by Cardinal who supplies companies such as Walgreens, King Soopers, Kroger and others.

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.

[edit] 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

[edit] Side effects

This section does not cite any references or sources. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (August 2008)

Possible side effects of secobarbital include:

• Somnolence
• Impaired motor functions
  • Impaired coordination
  • Impaired balance
  • Dizziness
• Anxiety
• Confusion
• Agitation, irritability, or excitability
• Headache
• Nausea
• Vomiting
• Nightmares
• Increased sensitivity to pain
• Allergic reactions
  • Difficulty breathing
  • Edema
  • Urticaria

[edit] Withdrawal

This section does not cite any references or sources. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (January 2008)

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

[edit] Recreational use

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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, "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 but is now rarely prescribed due to problems with abuse and overdose.

[edit] Cause of death of Judy Garland

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]

[edit] Cause of death of Alan Wilson

Alan Wilson, vocalist and founding member of Canned Heat, was found dead at age 27 in 1970, from a self-induced overdose of seconal. ^[3]

[edit] Cause of Death of Jimi Hendrix

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.

[edit] Cause of Death of Beverley Kenney

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.

[edit] Cause of Death of Carole Landis

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.

[edit] Use as a lethal injection

Secobarbital overdose was the most common method of implementing physician assisted suicide 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 PAD. Ranbaxy Laboratories Limited previously experienced approval issues in their attempts to produce 100 mg secobarbital capsules. Currently, Marathon Pharmaceuticals is the sole producer of the drug in the United States.

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

[edit] References

[edit] External links

• Marathon Pharmaceuticals - Seconal Full prescribing information for the United States.
• Drugs.com - Secobarbital
• RxList.com - Secobarbital Consumer information.

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