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Amobarbital

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Amobarbital
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administration		Oral,IM,IV,Rectal
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Legal status
Pharmacokineticdata
MetabolismHepatic
Eliminationhalf-life8–42 hours
ExcretionRenal
Identifiers
  • 5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione
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ECHA InfoCard100.000.300Edit this at Wikidata
Chemical and physical data
FormulaC11H18N2O3
Molar mass226.276g·mol−1
3D model (JSmol)
  • O=C1NC(=O)NC(=O)C1(CCC(C)C)CC
  • InChI=1S/C11H18N2O3/c1-4-11(6-5-7(2)3)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)checkY
  • Key:VIROVYVQCGLCII-UHFFFAOYSA-NcheckY
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Amobarbital(formerly known asamylobarbitoneorsodium amytalas the soluble sodium salt) is a drug that is abarbituratederivative. It hassedative-hypnoticproperties. It is a white crystalline powder with no odor and a slightly bitter taste. It was first synthesized inGermanyin 1923. It is considered a short to intermediate acting barbiturate.[citation needed]

If amobarbital is taken for extended periods of time, physiological andpsychological dependencecan develop. Amobarbital withdrawal mimicsdelirium tremensand may be life-threatening. Amobarbital was manufactured byEli Lilly and Companyin the US under the brand name Amytal in bright blue bullet shaped capsules (known as Pulvules) or pink tablets (known as Diskets)[2]containing 50, 100, or 200 milligrams of the drug. The drug was also manufactured generically.

Amobarbital was widely misused, known as "Blue Heavens" on the street. Amytal, as well as Tuinal, a combination drug containing equal quantities ofsecobarbitaland amobarbital, were both manufactured by Eli Lilly until the late-1990s. However, as the popularity of benzodiazepines increased, prescriptions for these medications became increasingly rare beginning in the mid to late-1980s.

Pharmacology[edit]

In anin vitrostudy in rat thalamic slices, amobarbital worked by activatingGABAAreceptors,which decreased input resistance, depressedburst and tonic firing,especially inventrobasal and intralaminarneurons,while at the same time increasing burst duration and meanconductanceat individualchloride channels;this increased both the amplitude and decay time ofinhibitorypostsynapticcurrents.[3]

Amobarbital has been used in a study to inhibit mitochondrial electron transport in the rat heart in an attempt to preserve mitochondrial function followingreperfusion.[4]

A 1988 study found that amobarbital increasesbenzodiazepine receptorbindingin vivowith less potency than secobarbital andpentobarbital(in descending order), but greater thanphenobarbitalandbarbital(in descending order).[5](Secobarbital > pentobarbital >amobarbital> phenobarbital > barbital)

It has anLD50in mice of 212mg/kg s.c.[citation needed]

Metabolism[edit]

Amobarbital undergoes bothhydroxylationto form 3'-hydroxyamobarbital,[6]andN-glucosidation[7]to form 1-(beta-D-glucopyranosyl)-amobarbital.[8]

Indications[edit]

Approved[edit]

Unapproved/off-label[edit]

When given slowly by an intravenous route, sodium amobarbital has a reputation for acting as a so-calledtruth serum.Under the influence, a person will divulge information that under normal circumstances they would block. This was most likely due to loss of inhibition. As such, the drug was first employed clinically byWilliam Bleckwennat the University of Wisconsin to circumvent inhibitions in psychiatric patients.[9]The use of amobarbital as a truth serum has lost credibility due to the discovery that a subject can be coerced into having a "false memory"of the event.[10]

The drug may be used intravenously to interview patients withcatatonicmutism,sometimes combined withcaffeineto prevent sleep.[11]

It was used by theUnited States armed forcesduringWorld War IIin an attempt to treatshell shockand return soldiers to thefront-lineduties.[12]This use has since been discontinued as the powerful sedation, cognitive impairment, and dis-coordination induced by the drug greatly reduced soldiers' usefulness in the field. Amobarbital was once manufactured in the US by Eli Lilly Pharmaceuticals under the brand name Amytal in capsule form. It was discontinued in the early 80s, largely replaced by the benzodiazepine family of drugs. Amobarbital was also widely abused, known on the streets as "blue heavens" because of their blue capsule.

Contraindications[edit]

Avialof Amytal sodium

The following drugs should be avoided when taking amobarbital:

Interactions[edit]

Amobarbital has been known to decrease the effects of hormonal birth control.[13]

Overdose[edit]

Some side effects of overdose include confusion (severe); decrease in or loss of reflexes; drowsiness (severe); fever; irritability (continuing); low body temperature; poor judgment; shortness of breath or slow or troubled breathing; slow heartbeat; slurred speech; staggering; trouble in sleeping; unusual movements of the eyes; weakness (severe). Severe overdose may result in death without intervention.

Chemistry[edit]

Amobarbital (5-ethyl-5-isoamylbarbituric acid), like all barbiturates, is synthesized by reactingmalonic acidderivatives withureaderivatives. In particular, in order to make amobarbital, α-ethyl-α-isoamylmalonic ester is reacted with urea (in the presence ofsodium ethoxide).[14][15]

Society and culture[edit]

It has been used to convict alleged murderers such asAndres English-Howard,who strangled his girlfriend to death but claimed innocence. He was surreptitiously administered the drug by his lawyer, and under the influence of it he revealed why he strangled her and under what circumstances.[16]

On the night of August 28, 1951, the housekeeper of actorRobert Walkerfound him to be in an emotional state. She called Walker's psychiatrist who arrived and administered amobarbital for sedation. Walker was allegedly drinking prior to his emotional outburst, and it is believed the combination of amobarbital andalcoholresulted in a severe reaction. As a result, he passed out and stopped breathing, and all efforts to resuscitate him failed. Walker died at 32 years old.

The British actor and comedianTony Hancockkilled himself in Australia in 1968 using the drug in combination with alcohol.

Eli Lilly manufactured amobarbital under the brand name Amytal, it was discontinued in the 1980s replaced largely by the benzodiazepine family of drugs. Amytal was also widely abused. Street names for amobarbital include "blues", "blue angels", "blue birds", "blue devils", and "blue heavens" due to their blue capsule.[17]

Cultural references[edit]

InLen Deighton's 1967 novelAn Expensive Place to Die,a combination of amytal andLSDis used to make the unnamed protagonist respond to questioning about his activities.

InThomas Pynchon's 1973 novelGravity's Rainbow,sodium amytal is used by a military intelligence unit as some kind of truth serum to extract Tyrone Slothrop's (the novel's protagonist) ideas on racism of white Americans against Afro-Americans during the 1930s in his home state of Massachusetts (Chapter 1).

In the 1975Columboepisode "A Deadly State of Mind"the victim Nadia Donner has Amobarbital found in her blood according to the autopsy report.[18][19][20]

In the 1994 comedic action thrillerTrue Lies,the protagonist Harry Tasker (portrayed byArnold Schwarzenegger) is given sodium amytal as a truth serum, when questioned by terrorists.

In 2001, theLaw & Order: Special Victims Unitepisode "Repression" (Season 3, Episode 1), a therapist (Shirley Knight) treats her patient with "sodium amytal". The character Dr.George Huang(BD Wong) claims that the drug leaves a patient so susceptible tosuggestion,that the therapist is able to implant false memories in the patient.

In 2003, the animated seriesSealab 2021season 3, episode 7, "Tourist Season", Dr. Quentin Q. Quinn, voiced by Brett Butler, uses "sodium amytal" to induce amnesia in a group of tourists, in order to prevent them from taking action against Sealab as a result of a hare-brained scheme by Capt. Murphy. He gives the dose in a free alcoholic beverage as a parting gift before the tourists leave, and in quantities he describes that could "make an elephant forget".

In the 2005 movie,Hellraiser: Hellworld,the main antagonist uses "sodium amytal" to secretly anesthetize the people he believes were responsible for his son's death, and induce extreme hallucinations in them.

In 2016, television dramaA Fist Within Four Wallsepisode 14, Man Zeun (portrayed by Princeton Lock) uses sodium amytal in an attempt to force gambling addict Lee Fat into paying debts.

In 2022, in "Diophantine Pseudonym", Episode 06 ofDan Brown'sThe Lost Symbol,sodium amytal is used by the CIA as a truth serum.

See also[edit]

Notes[edit]

  1. ^Anvisa(2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União(published 2023-04-04).Archivedfrom the original on 2023-08-03.Retrieved2023-08-16.
  2. ^Winek, Charles L. (1965-02-01)."Dosage Form Names and Product Identification".American Journal of Health-System Pharmacy.22(2): 84.doi:10.1093/ajhp/22.2.82.ISSN1079-2082.
  3. ^Kim HS, Wan X, Mathers DA, Puil E (October 2004)."Selective GABA-receptor actions of amobarbital on thalamic neurons".British Journal of Pharmacology.143(4): 485–94.doi:10.1038/sj.bjp.0705974.PMC1575418.PMID15381635.
  4. ^Stewart S, Lesnefsky EJ, Chen Q (May 2009). "Reversible blockade of electron transport with amobarbital at the onset of reperfusion attenuates cardiac injury".Translational Research.153(5): 224–31.doi:10.1016/j.trsl.2009.02.003.PMID19375683.
  5. ^Miller LG, Deutsch SI, Greenblatt DJ, Paul SM, Shader RI (1988). "Acute barbiturate administration increases benzodiazepine receptor binding in vivo".Psychopharmacology.96(3): 385–90.doi:10.1007/BF00216067.PMID2906155.S2CID29934652.
  6. ^Maynert EW (October 1965). "The alcoholic metabolites of pentobarbital and amobarbital in man".The Journal of Pharmacology and Experimental Therapeutics.150(1): 118–21.PMID5855308.
  7. ^Tang BK, Kalow W, Grey AA (July 1978). "Amobarbital metabolism in man: N-glucoside formation".Research Communications in Chemical Pathology and Pharmacology.21(1): 45–53.PMID684279.
  8. ^Soine PJ, Soine WH (November 1987). "High-performance liquid chromatographic determination of the diastereomers of 1-(beta-D-glucopyranosyl)amobarbital in urine".Journal of Chromatography.422:309–14.doi:10.1016/0378-4347(87)80468-1.PMID3437019.
  9. ^Bleckwenn WJ (1930). "Sodium amytal in certain nervous and mental conditions".Wisconsin Medical Journal.29:693–696.
  10. ^Stocks JT (September 1998). "Recovered memory therapy: a dubious practice technique".Social Work.43(5): 423–36.doi:10.1093/sw/43.5.423.PMID9739631.(subscription required)
  11. ^McCall WV (November 1992)."The addition of intravenous caffeine during an amobarbital interview".Journal of Psychiatry & Neuroscience.17(5): 195–7.PMC1188455.PMID1489761.
  12. ^"Use of sodium amytal during WWII".Battle of the Bulge - program transcript.PBS.Archivedfrom the original on 2009-03-14.Retrieved2017-08-24.Ben Kimmelman, Captain, 28th Infantry: The assumptions were that this would have some kind of cathartic effect, the sodium amytal, which the men calledblue 88's.You know, the most effective artillery piece of the Germans was the 88 and this wasblue 88s,because the sodium amytal was a blue tablet.
  13. ^"Amobarbital | Memorial Sloan Kettering Cancer Center".
  14. ^GB patent 191008,Layraud E, "The manufacture of unsymmetrical c.c.-dialkylbarbituric acids", issued 1923-10-25
  15. ^US patent 1856792,Shonle HA, "Anhydrous alkali salts of 5,5-di-aliphatic-substituted barbituric acids and processes of producing them", issued 1932-05-03
  16. ^Leung R (February 11, 2009)."Truth Serum: A Possible Weapon".60 Minutes.CBS News.Archivedfrom the original on April 5, 2005.RetrievedDecember 4,2005.
  17. ^"blue devils (amobarbital) - Memidex dictionary/thesaurus".memidex.
  18. ^Hart, Harvey (1975-04-27),A Deadly State of Mind,Columbo, Peter Falk, George Hamilton, Lesley Ann Warren,retrieved2024-01-11
  19. ^A Deadly State of Mind | Echoes of Columbo,retrieved2024-01-11
  20. ^"Episode review: Columbo A Deadly State of Mind".THE COLUMBOPHILE BLOG.2018-11-18.Retrieved2024-01-11.
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