| Revision as of 09:50, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 464254180 of page Amobarbital for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 05:50, 20 December 2024 edit 2601:c4:ca02:1720:f524:2850:600f:4e70 (talk) →Cultural references: Added contentTags: Mobile edit Mobile web edit |
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{{Short description|Barbiturate}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Infobox drug |
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{{Drugbox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| class = ] |
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| verifiedrevid = 456692007 |
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| verifiedrevid = 464364523 |
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| IUPAC_name = ''5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione'' |
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| IUPAC_name = 5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione |
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| image = Amobarbital.svg |
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| image = Amobarbital.svg |
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| width = 150 |
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| width = 120 |
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| image2 = Amobarbital ball-and-stick.png |
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| width2 = 200 |
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<!--Clinical data--> |
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| tradename = |
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<!--Clinical data-->| tradename = |
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| Drugs.com = {{drugs.com|CONS|amobarbital}} |
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| Drugs.com = {{drugs.com|CONS|amobarbital}} |
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| pregnancy_category = ? |
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| pregnancy_category = |
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| legal_BR = B1 |
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| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref> |
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| legal_CA = Schedule IV |
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| legal_CA = Schedule IV |
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| legal_US = |
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| legal_DE = Anlage III |
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| legal_status = ]/] (US) |
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| legal_US = Schedule II |
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| legal_US_comment = / ] |
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| routes_of_administration = Oral, ], ], Rectal |
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| legal_UK = Class B |
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| legal_UN = P III |
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<!--Pharmacokinetic data--> |
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| legal_status = SE: Förteckning IV |
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| bioavailability = ? |
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| licence_US = Amobarbital |
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| routes_of_administration = ], ], ], ] |
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<!--Pharmacokinetic data-->| bioavailability = |
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| metabolism = ] |
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| metabolism = ] |
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| elimination_half-life = 8-42 hours |
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| elimination_half-life = 8–42 hours |
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| excretion = ] |
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| excretion = ] |
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<!--Identifiers-->| CAS_number_Ref = {{cascite|correct|??}} |
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<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 57-43-2 |
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| CAS_number = 57-43-2 |
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| CAS_supplemental = 64-43-7 (sodium salt) |
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| CAS_supplemental = 64-43-7 (sodium salt) |
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| ATC_prefix = N05 |
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| ATC_prefix = N05 |
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| ATC_suffix = CA02 |
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| ATC_suffix = CA02 |
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| ATC_supplemental = |
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| ATC_supplemental = |
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| PubChem = 2164 |
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| PubChem = 2164 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB01351 |
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| DrugBank = DB01351 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 267894 |
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| ChEMBL = 267894 |
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<!--Chemical data-->| C = 11 |
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| H = 18 |
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<!--Chemical data--> |
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| C=11 | H=18 | N=2 | O=3 |
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| N = 2 |
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| O = 3 |
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| molecular_weight = 226.272 |
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| smiles = O=C1NC(=O)NC(=O)C1(CCC(C)C)CC |
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| smiles = O=C1NC(=O)NC(=O)C1(CCC(C)C)CC |
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| InChI = 1/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) |
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| InChIKey = VIROVYVQCGLCII-UHFFFAOYAO |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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) |
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| StdInChI = 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) |
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| StdInChIKey = VIROVYVQCGLCII-UHFFFAOYSA-N |
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| StdInChIKey = VIROVYVQCGLCII-UHFFFAOYSA-N |
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}} |
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}} |
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'''Amobarbital''' (formerly known as '''amylobarbitone''' or '''sodium amytal''' as the soluble sodium salt) is a drug that is a ] derivative. It has ]-] properties. It is a white crystalline powder with no odor and a slightly bitter taste. It was first synthesized in ] in 1923. It is considered a short to intermediate acting barbiturate. |
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If amobarbital is taken for extended periods of time, physiological and ] can develop. Amobarbital withdrawal mimics ] and may be life-threatening. Amobarbital was manufactured by ] in the United States under the brand name '''Amytal''' in bright blue bullet shaped capsules (known as Pulvules) or pink tablets (known as Diskets)<ref>{{Cite journal|last=Winek|first=Charles L.|date=1965-02-01|title=Dosage Form Names and Product Identification|url=https://academic.oup.com/ajhp/article/22/2/82/5212972|journal=American Journal of Health-System Pharmacy|language=en|volume=22|issue=2|pages=84|doi=10.1093/ajhp/22.2.82|issn=1079-2082}}</ref> containing 50, 100, or 200 milligrams of the drug. The drug was also manufactured generically. |
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Amobarbital was widely misused, known as "Blue Heavens" on the street. Amytal, as well as ], a combination drug containing equal quantities of ] and amobarbital, were both manufactured by Eli Lilly until the late 1990s. However, as the popularity of ] increased, prescriptions for these medications became increasingly rare beginning in the mid to late 1980s. |
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==Pharmacology== |
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In an '']'' study in rat thalamic slices, amobarbital worked by activating ]s, which decreased input resistance, depressed ], especially in ] ]s, while at the same time increasing burst duration and mean ] at individual ]s; this increased both the amplitude and decay time of ] ] ]s.<ref>{{cite journal | vauthors = Kim HS, Wan X, Mathers DA, Puil E | title = Selective GABA-receptor actions of amobarbital on thalamic neurons | journal = British Journal of Pharmacology | volume = 143 | issue = 4 | pages = 485–94 | date = October 2004 | pmid = 15381635 | pmc = 1575418 | doi = 10.1038/sj.bjp.0705974 }}</ref> |
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Amobarbital has been used in a study to inhibit mitochondrial electron transport in the rat heart in an attempt to preserve mitochondrial function following ].<ref>{{cite journal | vauthors = Stewart S, Lesnefsky EJ, Chen Q | title = Reversible blockade of electron transport with amobarbital at the onset of reperfusion attenuates cardiac injury | journal = Translational Research | volume = 153 | issue = 5 | pages = 224–31 | date = May 2009 | pmid = 19375683 | doi = 10.1016/j.trsl.2009.02.003 }}</ref> |
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A 1988 study found that amobarbital increases ] binding '']'' with less potency than secobarbital and ] (in descending order), but greater than ] and ] (in descending order).<ref>{{cite journal | vauthors = Miller LG, Deutsch SI, Greenblatt DJ, Paul SM, Shader RI | title = Acute barbiturate administration increases benzodiazepine receptor binding in vivo | journal = Psychopharmacology | volume = 96 | issue = 3 | pages = 385–90 | year = 1988 | pmid = 2906155 | doi = 10.1007/BF00216067 | s2cid = 29934652 }}</ref> (Secobarbital > pentobarbital > ''amobarbital'' > phenobarbital > barbital) |
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It has an {{LD50}} in mice of 212{{nbsp}}mg/kg s.c.{{Citation needed|date=November 2011}} |
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==Metabolism== |
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Amobarbital undergoes both ] to form 3'-hydroxyamobarbital,<ref>{{cite journal | vauthors = Maynert EW | title = The alcoholic metabolites of pentobarbital and amobarbital in man | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 150 | issue = 1 | pages = 118–21 | date = October 1965 | pmid = 5855308 }}</ref> and ]<ref>{{cite journal | vauthors = Tang BK, Kalow W, Grey AA | title = Amobarbital metabolism in man: N-glucoside formation | journal = Research Communications in Chemical Pathology and Pharmacology | volume = 21 | issue = 1 | pages = 45–53 | date = July 1978 | pmid = 684279 }}</ref> to form 1-(beta-D-glucopyranosyl)-amobarbital.<ref>{{cite journal | vauthors = Soine PJ, Soine WH | title = High-performance liquid chromatographic determination of the diastereomers of 1-(beta-D-glucopyranosyl)amobarbital in urine | journal = Journal of Chromatography | volume = 422 | pages = 309–14 | date = November 1987 | pmid = 3437019 | doi = 10.1016/0378-4347(87)80468-1 }}</ref> |
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==Indications== |
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===Approved=== |
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* ] |
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* ] |
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* ] |
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* ] |
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===Unapproved/off-label=== |
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When given slowly by an intravenous route, sodium amobarbital has a reputation for acting as a so-called ]. 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 by ] at the University of Wisconsin to circumvent inhibitions in psychiatric patients.<ref>{{ cite journal | vauthors = Bleckwenn WJ | year = 1930 | title = Sodium amytal in certain nervous and mental conditions | journal = Wisconsin Medical Journal | volume = 29 | pages = 693–696 }}</ref> The use of amobarbital as a truth serum has lost credibility due to the discovery that a subject can be coerced into having a "]" of the event.<ref name=Stocks>{{cite journal | vauthors = Stocks JT | title = Recovered memory therapy: a dubious practice technique | journal = Social Work | volume = 43 | issue = 5 | pages = 423–36 | date = September 1998 | pmid = 9739631 | doi = 10.1093/sw/43.5.423 }} {{subscription required}}</ref> |
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The drug may be used intravenously to interview patients with ] ], sometimes combined with ] to prevent sleep.<ref>{{cite journal | vauthors = McCall WV | title = The addition of intravenous caffeine during an amobarbital interview | journal = Journal of Psychiatry & Neuroscience | volume = 17 | issue = 5 | pages = 195–7 | date = November 1992 | pmid = 1489761 | pmc = 1188455 }}</ref> |
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It was used by the ] during ] in an attempt to treat ] and return soldiers to the ] duties.<ref>{{cite web |url=https://www.pbs.org/wgbh/amex/bulge/filmmore/pt.html |work=Battle of the Bulge - program transcript |title=Use of sodium amytal during WWII |quote=Ben Kimmelman, Captain, 28th Infantry: The assumptions were that this would have some kind of cathartic effect, the sodium amytal, which the men called ''blue 88's.'' You know, the most effective artillery piece of the Germans was the 88 and this was ''blue 88s'', because the sodium amytal was a blue tablet. |publisher=PBS |access-date=2017-08-24 |archive-url=https://web.archive.org/web/20090314070438/http://www.pbs.org/wgbh/amex/bulge/filmmore/pt.html |archive-date=2009-03-14 |url-status=live }}</ref> 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. |
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==Contraindications== |
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] of Amytal sodium]] |
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The following drugs should be avoided when taking amobarbital: |
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* ]s, such as ] and ] |
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* ]s, such as ] or ] |
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* ]s, such as ] and ] |
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* ]s, such as ] and ] |
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* ] |
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* ]s, such as ], ], ], ], or ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] ]s, such as ] and ] |
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* ] |
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* ]s, such as ] and ] |
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* ] |
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* ] |
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== Interactions == |
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Amobarbital has been known to decrease the effects of hormonal birth control.<ref>{{cite web | url=https://www.mskcc.org/pdf/cancer-care/patient-education/amobarbital-01 | title=Amobarbital | Memorial Sloan Kettering Cancer Center }}</ref> |
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==Overdose== |
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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. |
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==Chemistry== |
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] |
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Amobarbital (5-ethyl-5-isoamylbarbituric acid), like all barbiturates, is synthesized by reacting ] derivatives with ] derivatives. In particular, in order to make amobarbital, α-ethyl-α-isoamylmalonic ester is reacted with urea (in the presence of ]).<ref>{{ cite patent |
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| country = GB |
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| status = patent |
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| number = 191008 |
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| gdate = 1923-10-25 |
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| inventor = Layraud E |
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| title = The manufacture of unsymmetrical c.c.-dialkylbarbituric acids |
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}}</ref><ref>{{ cite patent |
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| country = US |
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| status = patent |
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| number = 1856792 |
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| gdate = 1932-05-03 |
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| inventor = Shonle HA |
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| title = Anhydrous alkali salts of 5,5-di-aliphatic-substituted barbituric acids and processes of producing them |
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}}</ref> |
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==Society and culture== |
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The drug has been used to gain confessions from murderers such as ], 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.<ref name=CBS>{{cite web |url= https://www.cbsnews.com/news/truth-serum-a-possible-weapon/ |title=Truth Serum: A Possible Weapon |publisher=] |work=] |date=February 11, 2009 | first = Rebecca | last = Leung | name-list-style = vanc |access-date=December 4, 2005 |archive-url= https://web.archive.org/web/20050405060256/http://www.cbsnews.com/stories/2003/04/07/60II/main548221.shtml |archive-date=April 5, 2005 |url-status=live }}</ref> |
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On the night of August 28, 1951, the housekeeper of actor ] found 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 and alcohol resulted 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. |
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The British actor and comedian ] killed himself in Australia in 1968 using the drug in combination with alcohol. |
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Eli Lilly manufactured amobarbital under the brand name Amytal until it was discontinued in the 1980s and 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.<ref>{{cite web|url=http://www.memidex.com/blue-devils+amobarbital|title=blue devils (amobarbital) - Memidex dictionary/thesaurus|work=www.memidex.com}}</ref> |
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==Cultural references== |
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In ]'s 1967 novel '']'', a combination of amytal and ] is used to make the unnamed protagonist respond to questioning about his activities. |
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In ]'s 1973 novel '']'', 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). |
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In the 1975 '']'' episode "]" the victim Nadia Donner has Amobarbital found in her blood according to the autopsy report.<ref>{{Citation |last=Hart |first=Harvey |title=A Deadly State of Mind |date=1975-04-27 |url=https://www.imdb.com/title/tt0072801/?ref_=tttrv_ov |access-date=2024-01-11 |series=Columbo |others=Peter Falk, George Hamilton, Lesley Ann Warren}}</ref><ref>{{Citation |title=A Deadly State of Mind {{!}} Echoes of Columbo | date=16 September 2020 |url=https://www.youtube.com/watch?v=wB6hqrBcTdQ |access-date=2024-01-11 |language=en}}</ref><ref>{{Cite web |date=2018-11-18 |title=Episode review: Columbo A Deadly State of Mind |url=https://columbophile.com/2018/11/18/episode-review-columbo-a-deadly-state-of-mind/ |access-date=2024-01-11 |website=THE COLUMBOPHILE BLOG |language=en-US}}</ref> |
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In the 1994 comedic action thriller '']'', the protagonist Harry Tasker (portrayed by ]) is given sodium amytal as a truth serum, when questioned by terrorists. |
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In 2001, the '']'' episode "Repression" (]), a therapist (]) treats her patient with "sodium amytal". The character Dr. ] (]) claims that the drug leaves a patient so susceptible to ], that the therapist is able to implant false memories in the patient. |
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In 2003, the animated series '']'' season 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". |
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In the 2005 movie, '']'', 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. |
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Hannibal s2e4. |
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In 2016, television drama '']'' episode 14, Man Zeun (portrayed by Princeton Lock) uses sodium amytal in an attempt to force gambling addict Lee Fat into paying debts. |
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In 2022, in "Diophantine Pseudonym", Episode 06 of ]'s '']'', sodium amytal is used by the CIA as a truth serum. |
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== See also == |
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* ] |
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* ] |
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* ] |
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== Notes == |
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{{Reflist}} |
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{{Hypnotics and sedatives}} |
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{{GABAAR PAMs}} |
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] |
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] |
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] |
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] |
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] |