pentobarbital sodium

Pentobarbital

Systematic (IUPAC) name
5-Ethyl-5-(1-methylbutyl)- 2,4,6(1H,3H,5H)-pyrimidinetrione
Identifiers
CAS number	76-74-4
ATC code	N05CA01 QN51AA01
PubChem	4737
DrugBank	APRD01174
ChemSpider	4575
Chemical data
Formula	C11H18N2O3
Mol. mass	226.27
Pharmacokinetic data
Bioavailability	70-90% oral; 90% rectal
Protein binding	20-45%
Metabolism	Hepatic
Half life	15-48 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	D (USA)
Legal status	USA: Schedule II (oral and parenteral); Schedule III (rectal)
Routes	Oral, Intravenous, Intramuscular, Rectal; also Intraperitoneal & Intracardiac (for animal euthanasia)
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Pentobarbital is a short-acting barbiturate that was first synthesized in 1928. Pentobarbital is available as both a free acid and a sodium salt, the former of which is only slightly soluble in water and ethanol.^[1] One trade name for this drug is Nembutal, coined by Dr. John S. Lundy, who started using it in 1930, from the structural formula of the sodium salt—Na (sodium) + ethyl + methyl + butyl + al (common suffix for barbiturates).^[2]

Uses

Approved

Pentobarbital's FDA approved human uses include treatment of seizures and preoperative (and other) sedation; it is also approved as a short-term hypnotic.^[3]

In France and the Netherlands, it is no longer used in the treatment of insomnia, nor as a preanesthetic.^[4]

Unapproved/Investigational/Off-Label

Off-label uses of pentobarbital include reduction of intracranial pressure in Reye's syndrome, traumatic brain injury^[1] and induction of coma in cerebral ischemia patients.^[3]

Veterinary medicine

In veterinary medicine, sodium pentobarbital—traded under names such as Sagatal—is used as an anaesthetic.^[5] Pentobarbital is an ingredient in Equithesin.

Veterinary euthanasia

It is used by itself, or more often in combination with complementary agents such as phenytoin, in commercial animal euthanasia^[6] injectable solutions. Trade names include Euthasol, Euthatal, Euthanal, Euthanyl (in Canada), Beuthanasia-D, and Fatal Plus.

Human euthanasia

Pentobarbital has also been used for physician assisted suicide. It is commonly used in the US state of Oregon for this purpose.^[7], and is also used by the Swiss euthanasia group Dignitas. Pentobarbital was also used for this purpose in the Northern Territory of Australia, prior to euthanasia becoming illegal in that region.

In the Netherlands, a pentobarbital elixir is used as an alternative for patients who wish to take the barbiturate needed for the lethal cocktail themselves, instead of having it administered intravenously, in which case thiopental is used. Pentobarbital has no medical use anymore in the Netherlands, and is only used for euthanasia.

Typically, when orally ingested for euthanasia purposes, an anti-emetic drug is swallowed approximately 30 minutes before the lethal overdose of pentobarbital. This is done because large concentrated doses of pentobarbital may cause vomiting.

In this role, Pentobarbital is highly sought after by people wishing to end their lives but not allowed to do so under their country's laws. It is therefore often smuggled across borders from countries where it is still available over-the-counter such as Mexico, or purchased through illegal mail orders^[8]. It has been described as one of the most peaceful ways to commit suicide.

Death penalty

Sodium pentobarbital is also used for executions by lethal injection in China, not in the United States.

Metabolism

Pentobarbital undergoes first-pass metabolism in the liver and possibly the intestines.^[9]

Drug interactions

Administration of alcohol, opioids, antihistamines, other sedative-hypnotics, and other central nervous system depressants will greatly increase the sedation effects and risk of accidental death caused by pentobarbital.^[3]

Recreational use

Pentobarbital is a drug that has been used recreationally under the slang term "yellow-jacket." Two types of drug use can occur: recreational use, where the drug is taken to achieve a high, or when the drug is continued long term against medical advice.^[10]

References in popular culture

This "In popular culture" section may contain too many minor or trivial references. Please reorganize this content to explain the subject's impact on popular culture rather than simply listing appearances, and remove trivia references. (October 2009)

A pentobarbital suppository was cited in an October 2006 news article^[11] in WorldNetDaily.com as the cause of death of Marilyn Monroe. The Coroners report of Marilyn Monroes death concluded her death was due to a massive overdose of 47 Nembutal capsules.

The Clash makes a reference to it in the song The Right Profile from the album London Calling in which the lyrics read "Nembutal numbs it all, but I prefer... alcohol!"

The song "Yellow Submarine" by The Beatles is rumoured to refer to Nembutal due to the color and shape of the capsules. However, Paul McCartney has denied this, stating that he had written the song as a children's tune.

The song "Cerrado por Derribo" by Joaquín Sabina references Nembutal in its lyrics.

A song by Jets To Brazil references Nembutal in the line "with nembutal bought from some doctor who also was bought to keep those pockets full" in the song Conrad, which confronts the issue of suicide through its lyrics. The song was later covered by the band Cassino (band)

An official autopsy on Jim Jones, famed leader of the cult murder/suicide of over 900 people in Guyana, found very large quantities of Pentobarbital in his system. He probably died by gunshot however.^[12]

In the 1957 novel On the Beach by Nevil Shute, the Australian government mass-distributes Nembutal in red cartons for voluntary euthanasia as radiation sickness spreads south in the final days of mankind following World War III.^[13]

Singer Kristin Hersh references the drug in her song "Sno-Cat" with the lyric: "Snow buries Whitehall / White powdered Nembutol."

The American progressive band The Mars Volta references the drug in the title of the song "Halo of Nembutals" from the 2009 album, Octahedron

A character in Neil Simon's play Barefoot in the Park suggests spiking another character's drink with Nembutol to calm him down.

Pentobarbital is refered to in William S. Burroughs's novel Junky as "Nembutal" "Nembies" and "Goofballs". In the novel it is used to help through heroin withdrawal.

In The Yiddish Policemen's Union by Michael Chabon the main character's (Landsman) father kills himself with an overdose of Nembutal.

References