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
PubChem	5193
DrugBank	APRD00497
Chemical data
Formula	C₁₂H₁₈N₂O₃
Mol. mass	238.283
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Half life	?
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	D (USA)
Legal status	Schedule II (USA)
Routes	Oral

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

1 Indications
2 Availability
- 2.1 Secobarbital sodium
3 Side effects
4 Withdrawal
5 Recreational Use
6 Use as a lethal injection
7 References
8 External links

[edit] Indications

Secobarbital is indicated for:

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

[edit] 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.

[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

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

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

Insomnia
REM rebound
Anxiety
Tremors
Seizures
Lack of appetite

[edit] 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" (it was originally packaged in red capsules). Another common nickname is "seccies". 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 Charles Boyer

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

[edit] 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.

[edit] 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 1.5-grain Seconal capsules.^[1]

[edit] 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 Secobarbital tablets after a night of drinking wine and was later found dead in his London apartment. Hendrix' death was caused by asphyxiation, after Hendrix presumably vomited in his sleep as a result of the mixture of the excessive Secobarbital dose and alcohol.

[edit] Role in Death of Anissa Jones

Her 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.

[edit] Cause of Death Carol Landis

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

[edit] Cause of Death of Marilyn Monroe

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

[edit] 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.