Secobarbital

Secobarbital

Systematic (IUPAC) name
5-[(2R)-pentan-2-yl]-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
Clinical data
Trade names	Seconal
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a682386
Pregnancy cat.	D (United States)
Legal status	Schedule II (US)
Routes	Oral
Pharmacokinetic data
Bioavailability	?
Protein binding	45-60%[1]
Metabolism	Hepatic
Half-life	15-40 hours[1]
Excretion	Renal
Identifiers
CAS number	76-73-3 Y
ATC code	N05CA06 QN51AA02
PubChem	CID 5193
DrugBank	APRD00497
ChemSpider	5005 Y
UNII	1P7H87IN75 Y
KEGG	D00430 Y
ChEBI	CHEBI:9073 Y
ChEMBL	CHEMBL447 Y
Chemical data
Formula	C12H18N2O3
Mol. mass	238.283
SMILES	eMolecules & PubChem
InChI 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) Y Key:KQPKPCNLIDLUMF-UHFFFAOYSA-N Y
N(what is this?)  (verify)

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 in Germany. 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
• Use as a preoperative medication to produce anaesthesia and anxiolysis in short surgical, diagnostic, or therapeutic procedures which are minimally painful.

Availability

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, the current marketer. The date of return of 100 mg Seconal capsules can be confirmed by US distributor Cardinal and/or pharmacies such as King Soopers and Walgreens that carry or special order Marathon Seconal since 2009. Seconal returned to the market in January 2009.(see http://www.tititudorancea.com/z/secobarbital.htm) 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:

• 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

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 withdrawal

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.

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 Thurston was accidental overdose of barbiturates; her blood contained the equivalent of 10 Seconal 100 mg capsules.^[2]
• Brian Epstein, the Beatles' manager, died at his house in London on 27 August 1967. The stated exact cause of death by coroner Gavin Thurston was accidental overdose of barbiturates
• 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 but later reports indicated the Seconal connection.^[3]
• Jimi Hendrix, guitarist and vocalist, died while at girlfriend's Monika Dannemann flat in London. The coroner Gavin Thurston accepted that he had probably taken nine of his girlfriend's tablets, after which he vomited and choked to death due to the tablets. He gave an open verdict (not enough evidence to say why he took so many tablets). He died September 18, 1970 aged 27.
• 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]
• Dorothy Kilgallen, an American journalist and television game show panelist, was found dead on November 8, 1965, having apparently succumbed to a fatal combination of alcohol and Seconal, possibly concurrent with a heart attack.
• Dinah Washington, blues, R&B and jazz singer, was found dead at age 39 in 1963, from a lethal combination of secobarbital and amobarbital.^[5]
• 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 Pacific Palisades, California home on July 5, 1948. She was 29.
• Lupe Vélez, a Mexican-born film actress, committed suicide in 1944 with an overdose of Seconal. The story (which gained notoriety when described in Kenneth Anger's Hollywood Babylon and inspired Andy Warhol's film Lupe) that she died with her head jammed down the lavatory after slipping on vomit, is an urban legend.
• Aimee Semple McPherson a Canadian-born evangelist and media celebrity in the 1920s and 1930s was found in a hotel room unconscious on September 26, 1944 after taking Seconal.
• Leila Pahlavi (27 March 1970 – 10 June 2001) Leila Pahlavi was the youngest daughter of the Late Shah of Iran, Mohammad Reza Pahlavi and his wife Empress Farah. On Sunday 10 June 2001, Leila was found dead in her room in the Leonard Hotel in London just before 19:30 BST by her doctor. She was found to have more than five times the lethal dose of secobarbital in her system, along with a nonlethal amount of cocaine.
• Charles Boyer (28 August 1899 – 26 August 1978) was a French actor who appeared in more than 80 films between 1920 and 1976. On 26 August 1978, two days after his wife died from cancer, and two days before his own 79th birthday, Boyer committed suicide with an overdose of Seconal while at a friend's home in Scottsdale.
• Poet Alejandra Pizarnik died in Buenos Aires of a self-induced overdose of Seconal.
• Singer Phyllis Hyman (July 6, 1949 – June 30, 1995) committed suicide by overdosing on pentobarbital and secobarbital in her New York City apartment.

Use as lethal injection

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. 
5. ^ "Queen: The Life and Music of Dinah Washington" Nadine Cohodas 2004

External links

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