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| {{Drugbox|
| | #REDIRECT [[Amobarbital sodium]] |
| | IUPAC_name = ''5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione''
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| | image =
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| | width = 150
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| | CAS_number = 57-43-2
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| | CAS_supplemental = 64-43-7 (sodium salt)
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| | ATC_prefix = N05
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| | ATC_suffix = CA02
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| | ATC_supplemental =
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| | PubChem = 2164
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| | DrugBank = none
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| | chemical_formula =
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| | C = 11 | H = 18 | N = 2 | O = 3
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| | molecular_weight = 226.272
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| | bioavailability = ?
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| | metabolism = [[Hepatic]]
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| | elimination_half-life = 8-42 hours
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| | excretion = [[Renal]]
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| | pregnancy_category = ?
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| | legal_US =
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| | legal_CA = Schedule IV
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| | legal_status = [[Schedule II]]/[[Schedule III]] ([[United States|US]])
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| | routes_of_administration = Oral, [[IM]], [[IV]], Rectal
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| }}
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| {{SI}}
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| ==Overview==
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| '''Amobarbital''' (formerly known as amylobarbitone) is a drug that is a [[barbiturate]] derivative. It has [[sedative]]-[[hypnotic]] and [[analgesic]] properties. It is a white crystalline powder with no odor and a slightly bitter taste. If amobarbital is taken for extended periods of time, physical and psychological dependence can develop.
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| ==Pharmacology==
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| According to an ''[[in vitro]]'' study conducted at the University of British Columbia, amobarbital works by activating [[GABA A receptor|GABA<sub>A</sub> receptor]]s, which decreases input resistance, depresses [[action potential|burst]] and [[action potential|tonic firing]], especially in [[thalamus|ventrobasal]] and [[thalamus|intralaminar]] [[neuron]]s, while at the same time increasing burst duration and mean [[conductance]] at individual [[chloride channel]]s; this increases both the amplitude and decay time of [[postsynaptic]] [[current (electricity)|current]]s.<ref name=mechanism>Kim HS, Wan X, Mathers DA, Puil E. [http://www.nature.com/bjp/journal/v143/n4/full/0705974a.html "Selective GABA-receptor actions of amobarbital on thalamic neurons."] ''British Journal of Pharmacology.'' 2004 Oct;143(4):485-94. Epub 2004 Sep 20. PMID 15381635</ref>
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| It has an [[LD50|LD<sub>50</sub>]] in mice of 212 mg/kg s.c.
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| ==Metabolism==
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| Amobarbital undergoes both [[hydroxylation]] to form 3'-hydroxyamobarbital,<ref name=hydroxy>Maynert EW. "The alcoholic metabolites of pentobarbital and amobarbital in man." ''Journal of Pharmacology and Experimental Therapeutics.'' 1965 Oct;150(1):118-21. PMID 5855308</ref> which has both [[levorotatory]] and [[dextrorotatory]] [[isomer]]s<ref name=hydroxy-isomer>[http://ctd.mdibl.org/voc.go?voc=chem&termUI=3'-hydroxyamobarbital Chemicals: 3'-hydroxyamobarbital] The Comparative Toxicology Database.</ref> and [[glucoside|N-glucosidation]]<ref name=N-glucoside-formation>Tang BK, Kalow W, Grey AA. "Amobarbital metabolism in man: N-glucoside formation." ''Research Communications in Chemical Pathology and Pharmacology.'' 1978 Jul;21(1):45-53. PMID 684279</ref> to form 1-(beta-D-glucopyranosyl)amobarbital.<ref name=N-glucoside-name>Soine PJ, Soine WH. "High-performance liquid chromatographic determination of the diastereomers of 1-(beta-D-glucopyranosyl)amobarbital in urine." ''Journal of Chromatography.'' 1987 Nov 27;422:309-14. PMID 3437019</ref> | |
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| ==Indications==
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| ====Approved====
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| * [[Anxiety]]
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| * [[Insomnia]]
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| * [[Epilepsy]]
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| ====Unapproved/Off-Label====
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| * Sodium amobarbital has a reputation for having activity as a truth serum, where the person under the influence of the drug will submit to almost any request given by another person. It has been used to convict murderers such as Andres English-Howard, who strangled his girlfriend to death but claimed innocence. He was surreptitiously administered the drug, by his attorney, and under the influence of it he revealed why he strangled her and under which circumstances. A year later he confessed, on the stand, and was convicted on the basis of these statements; he later committed suicide in his cell.<ref name=CBS>[http://www.cbsnews.com/stories/2003/04/07/60II/main548221.shtml Truth Serum: A Possible Weapon], ''60 Minutes'', April 23, 2003.</ref> The use of amobarbital as a truth serum has lost credibility due to the discovery that the subject can be coerced into having a '[[false memory]]' of the event. In controlled doses, it is used in the [[Narco Analysis]] test to trace crime and criminals in modern [[forensics]].
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| * [[catatonia|Catatonic]] [[Speech disorder|mutism]], sometimes combined with [[caffeine]] to combat [[somnolence]].<ref name=amobarbmutcaff>McCall WV. "The addition of intravenous caffeine during an amobarbital interview." ''Journal of Psychiatry & Neuroscience.'' 1992 Nov;17(5):195-7. PMID 1489761</ref>
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| * It was also used in the Battle of the Bulge as a healing pill to send people back to the front.<ref>[http://www.pbs.org/wgbh/amex/bulge/filmmore/pt.html Use of sodium amytal during WWII]</ref>
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| ==Contraindications==
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| The following drugs should be avoided when taking amobarbital:
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| * [[ethyl alcohol|Alcohol]]
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| * [[Caffeine]]
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| * [[Chloramphenicol]]
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| * [[Chlorpromazine]]
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| * [[Cyclophosphamide]]
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| * [[Ciclosporin]]
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| * [[Digitoxin]]
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| * [[Doxorubicin]]
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| * [[Doxycycline]]
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| * [[Methoxyflurane]]
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| * [[Metronidazole]]
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| * [[Quinine]]
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| * [[Theophylline]]
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| * [[Warfarin]]
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| * [[Benzodiazepine]]s, such as [[diazepam]], [[clonazepam]] or [[nitrazepam]]
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| * [[Antiepileptic]]s, such as [[phenobarbital]] or [[carbamazepine]]
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| * [[Antihistamine]]s, such as [[doxylamine]] and [[clemastine]]
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| * [[Narcotic]] [[analgesic]]s, such as [[morphine]] and [[oxycodone]]
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| * [[Steroid]]s, such as [[prednisone]] and [[cortisone]]
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| * [[Antidepressant]]s
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| * [[Antihypertensive]]s, such as [[atenolol]] and [[propranolol]]
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| * [[Antiarrhythmic]]s, such as [[verapamil]] and [[digoxin]]
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| Amobarbital has been known to decrease the effects of hormonal birth control, sometimes to the point of uselessness. Being chemically related to [[phenobarbital]], it might also do the same thing to [[digitoxin]], a [[cardiac glycoside]].
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| In 1988, Miller et al reported that amobarbital increases benzodiazepine receptor binding ''[[in vivo]]'' with less potency than [[secobarbital]] and [[pentobarbital]] (in descending order), but greater than phenobarbital and [[barbital]] (in ascending order).<ref name=not_with_benzos>{{cite journal | author=Miller LG, Deutsch SI, Greenblatt DJ, Paul SM, Shader RI | title=Acute barbiturate administration increases benzodiazepine receptor binding in vivo | journal=Psychopharmacology (Berl) | volume=96 | issue=3 | year=1988 | pages=385-90}} PMID 2906155</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). Death can be a result.
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| ==See also==
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| * [[Depressants]]
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| * [[Barbiturates]]
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| * [[Wada test]]
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| ==References and End Notes==
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| {{Reflist}}
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| # [http://www.deadiversion.usdoj.gov/schedules/listby_sched/sched2.htm Controlled Substances in Schedule II] Office of Diversion Control, Drug Enforcement Administration.
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| # [http://www.deadiversion.usdoj.gov/schedules/listby_sched/sched3.htm Controlled Substances in Schedule III] Office of Diversion Control, Drug Enforcement Administration.
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| ==External links==
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| {{Barbiturates}}
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| {{Hypnotics and sedatives}}
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| [[de:Amobarbital]]
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| [[gl:Amobarbital]]
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| [[ja:アモバルビタール]]
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| [[ru:Эстимал]]
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| [[sl:Amobarbiton]]
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| [[fi:Amobarbitaali]]
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| [[sv:Amobarbital]]
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| [[zh:异戊巴比妥]]
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| [[Category:Drugs]]
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