Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/03/05 06:53:48」(JST)

wiki en

Amobarbital (formerly known as amylobarbitone or sodium amytal) is a drug that is a barbiturate derivative. It has sedative-hypnotic properties. It is a white crystalline powder with no odor and a slightly bitter taste. It was first synthesized in Germany in 1923. If amobarbital is taken for extended periods of time, physical and psychological dependence can develop. Amobarbital withdrawal mimics delirium tremens and may be life-threatening.

Pharmacology

In an in vitro study in rat thalamic slices amobarbital worked by activating GABA_A receptors, which decreased input resistance, depressed burst and tonic firing, especially in ventrobasal and intralaminar neurons, while at the same time increasing burst duration and mean conductance at individual chloride channels; this increased both the amplitude and decay time of inhibitory postsynaptic currents.^[1]

Amobarbital has been used in a study to inhibit mitochondrial electron transport in the rat heart.^[2]

A 1988 study found 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 descending order).^[3]

It has an LD₅₀ in mice of 212 mg/kg s.c.^{[citation needed]}

Metabolism

Amobarbital undergoes both hydroxylation to form 3'-hydroxyamobarbital,^[4] and N-glucosidation^[5] to form 1-(beta-D-glucopyranosyl)amobarbital.^[6]

Indications

Approved

Anxiety
Epilepsy
Insomnia
Wada test

Unapproved/off-label

When given slowly by an intravenous route, sodium amobarbital has a reputation for acting as a so-called truth serum. Under the influence, a person will divulge information that under normal circumstances they would block. As such, the drug was first employed clinically by Dr. William Bleckwenn at the University of Wisconsin to circumvent inhibitions in psychiatric patients.^[7] 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.^[8]

The drug may be used intravenously to interview patients with catatonic mutism, sometimes combined with caffeine to prevent sleep.^[9]

It was used by the United States armed forces during World War II in an attempt to treat shell shock and return soldiers to the front-line duties.^[10] 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.

Contraindications

A vial of amytal sodium

The following drugs should be avoided when taking amobarbital:

Antiarrhythmics, such as verapamil and digoxin
Antiepileptics, such as phenobarbital or carbamazepine
Antihistamines, such as doxylamine and clemastine
Antihypertensives, such as atenolol and propranolol
Alcohol^{[citation needed]}
Benzodiazepines, such as diazepam, clonazepam or nitrazepam
Caffeine^{[citation needed]}
Chloramphenicol
Chlorpromazine
Cyclophosphamide
Ciclosporin
Digitoxin
Doxorubicin
Doxycycline
Methoxyflurane
Metronidazole
Narcotic analgesics, such as morphine and oxycodone
Quinine
Steroids, such as prednisone and cortisone
Theophylline
Warfarin

Interactions

Amobarbital has been known to decrease the effects of hormonal birth control, sometimes to the point of uselessness.^{[citation needed]} Being chemically related to phenobarbital, it might also do the same thing to digitoxin, a cardiac glycoside.^{[citation needed]}

Overdose

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).

Chemistry

Amobarbital (5-ethyl-5-isoamylbarbituric acid), like all barbiturates, is synthesized by reacting malonic acid derivatives with urea derivatives. In particular, in order to make amobarbital, α-ethyl-α-isoamylmalonic ester is reacted with urea (in the presence of sodium ethoxide).^[11]^[12]

Society and culture

It has been used to convict alleged murderers such as Andres 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. A year later he confessed on the witness stand and was convicted on the basis of these statements. He later committed suicide in his cell.^[13] James Forrestal underwent a psychiatric treatment with sodium amytal.

On the night of August 28, 1951, Robert Walker's housekeeper found the actor 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.

References and end notes

^ Kim, H. -S.; Wan, X.; Mathers, D. A.; Puil, E. (2004). "Selective GABA-receptor actions of amobarbital on thalamic neurons". British Journal of Pharmacology 143 (4): 485–494. doi:10.1038/sj.bjp.0705974. PMC 1575418. PMID 15381635.
^ Stewart, S.; Lesnefsky, E. J.; Chen, Q. (2009). "Reversible blockade of electron transport with amobarbital at the onset of reperfusion attenuates cardiac injury". Translational Research 153 (5): 224–231. doi:10.1016/j.trsl.2009.02.003. PMID 19375683.
^ Miller, L. G.; Deutsch, S. I.; Greenblatt, D. J.; Paul, S. M.; Shader, R. I. (1988). "Acute barbiturate administration increases benzodiazepine receptor binding in vivo". Psychopharmacology 96 (3): 385–390. doi:10.1007/BF00216067. PMID 2906155.
^ Maynert, E. W. (1965). "The alcoholic metabolites of pentobarbital and amobarbital in man". The Journal of Pharmacology and Experimental Therapeutics 150 (1): 118–121. PMID 5855308.
^ Tang, B. K.; Kalow, W.; Grey, A. A. (1978). "Amobarbital metabolism in man: N-glucoside formation". Research communications in chemical pathology and pharmacology 21 (1): 45–53. PMID 684279.
^ Soine, P. J.; Soine, W. H. (1987). "High-performance liquid chromatographic determination of the diastereomers of 1-(beta-D-glucopyranosyl)amobarbital in urine". Journal of chromatography 422: 309–314. doi:10.1016/0378-4347(87)80468-1. PMID 3437019.
^ Bleckwenn, W. J. (1930). "Sodium amytal in certain nervous and mental conditions". Wisconsin Medical Journal 29: 693–696.
^ Stocks, J. T. (1998). "Recovered memory therapy: A dubious practice technique". Social work 43 (5): 423–436. doi:10.1093/sw/43.5.423. PMID 9739631.
^ McCall, W. V. (1992). "The addition of intravenous caffeine during an amobarbital interview". Journal of psychiatry & neuroscience : JPN 17 (5): 195–197. PMC 1188455. PMID 1489761.
^ "Use of sodium amytal during WWII". Battle of the Bulge - program transcript. PBS. 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.
^ GB patent 191008, Layraud, E., "The manufacture of unsymmetrical c.c.-dialkylbarbituric acids", issued 1923-10-25
^ US patent 1856792, Shonle, H. A., "Anhydrous alkali salts of 5,5-di-aliphatic-substituted barbituric acids and processes of producing them", issued 1932-05-03
^ Rebecca Leung (February 11, 2009). "Truth Serum: A Possible Weapon". 60 Minutes. CBS News.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 成人におけるてんかんの外科的治療 surgical treatment of epilepsy in adults
2. 成人における緊張病：疫学、臨床的特徴、評価、および診断 catatonia in adults epidemiology clinical features assessment and diagnosis
3. 痙攣発作およびてんかんの評価における神経画像 neuroimaging in the evaluation of seizures and epilepsy
4. 緊張病：治療および予後 catatonia treatment and prognosis
5. 子癇 eclampsia

English Journal

Resting-State Functional MR Imaging for Determining Language Laterality in Intractable Epilepsy.

DeSalvo MN1, Tanaka N1, Douw L1, Leveroni CL1, Buchbinder BR1, Greve DN1, Stufflebeam SM1.
Radiology.Radiology.2016 Jul 28:141010. [Epub ahead of print]
Purpose To measure the accuracy of resting-state functional magnetic resonance (MR) imaging in determining hemispheric language dominance in patients with medically intractable focal epilepsies against the results of an intracarotid amobarbital procedure (IAP). Materials and Methods This study was a
PMID 27467465

An improved qEEG index for asymmetry detection during the Wada test.

Bogaarts G1, Gommer E2, Hilkman D2, van Kranen-Mastenbroek V2, Reulen J2.
Epilepsy & behavior : E&B.Epilepsy Behav.2016 Jul 20;62:40-46. doi: 10.1016/j.yebeh.2016.06.009. [Epub ahead of print]
The Wada test is commonly used to evaluate language and memory lateralization in candidates for epilepsy surgery. The spatial Brain Symmetry Index (BSI) quantifies inter-hemispheric differences in the EEG. Its application has been shown to be feasible during Wada testing. We developed a method for t
PMID 27450303

Rapid determination of nine barbiturates in human whole blood by liquid chromatography-tandem mass spectrometry.

Zhang X1,2, Lin Z2, Li J3, Huang Z2, Rao Y2, Liang H2, Yan J4, Zheng F1.
Drug testing and analysis.Drug Test Anal.2016 Jul 1. doi: 10.1002/dta.2002. [Epub ahead of print]
A rapid, simple and sensitive liquid chromatography-tandem mass spectrometry (LC-MS/MS) method was developed for the qualitative and quantitative analysis of nine barbiturates (barbital, phenobarbital, pentobarbital, amobarbital, secobarbital, thiopental, butalbital, butabarbital, and hexobarbital)
PMID 27368111

Japanese Journal

Intracarotid sodium amylobarbitone and cerebral dominance for speech and consciousness

SERAFETINIDES EA
Brain 88, 107-130, 1965
NAID 30024510440

The influence of amobabital (amylobarbitone) and methamphetamine on the focus of attention

CALLAWAY E.
Journal of Mental Science 105, 382-392, 1959
NAID 30039177984

Related Pictures

Drawing of Amobarbital (amylobarbitone) barbiturate sedative, chemical csp15019749 Stock Illustration - Amobarbital (amylobarbitone) barbiturate sedative, chemical stru Euthanasia Illustrations and Clipart. 36 euthanasia royalty free illustrations, and 301 Moved Permanently Barbiturate Stock Photos & Barbiturate Stock Images - Alamy Amobarbital; Amylobarbitone; Pentymal Stock Photographs of Amobarbital (amylobarbitone) barbiturate sedative, chemical

★リンクテーブル★

リンク元	「アモバルビタール」

「アモバルビタール」

Amobarbital
Systematic (IUPAC) name
	5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	?;
Routes of; administration	Oral, IM, IV, Rectal
Legal status	CA: Schedule IV; DE: Anlage III; Schedule II/Schedule III (US);
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Biological half-life	8–42 hours
Excretion	Renal
Identifiers
CAS Number	57-43-2 64-43-7 (sodium salt)
ATC code	N05CA02
PubChem	CID 2164
DrugBank	DB01351
ChemSpider	2079
UNII	GWH6IJ239E
KEGG	D00555
ChEBI	CHEBI:2673
ChEMBL	CHEMBL267894
Chemical data
Formula	C11H18N2O3
Molar mass	226.272
	SMILES O=C1NC(=O)NC(=O)C1(CCC(C)C)CC ;
	InChI 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) ; Key:VIROVYVQCGLCII-UHFFFAOYSA-N ;
(verify)

　　[★]

英: amobarbital、amobarbital sodium
ラ: amobarbitalum
同: アミロバルビトン amylobarbitone
商: イソミタール、イソミタールソーダ
関: アモバルビタールナトリウム。アミタール

[1] Kim, H. -S.; Wan, X.; Mathers, D. A.; Puil, E. (2004). "Selective GABA-receptor actions of amobarbital on thalamic neurons". British Journal of Pharmacology 143 (4): 485–494. doi:10.1038/sj.bjp.0705974. PMC 1575418. PMID 15381635.

[2] Stewart, S.; Lesnefsky, E. J.; Chen, Q. (2009). "Reversible blockade of electron transport with amobarbital at the onset of reperfusion attenuates cardiac injury". Translational Research 153 (5): 224–231. doi:10.1016/j.trsl.2009.02.003. PMID 19375683.

[3] Miller, L. G.; Deutsch, S. I.; Greenblatt, D. J.; Paul, S. M.; Shader, R. I. (1988). "Acute barbiturate administration increases benzodiazepine receptor binding in vivo". Psychopharmacology 96 (3): 385–390. doi:10.1007/BF00216067. PMID 2906155.

[4] Maynert, E. W. (1965). "The alcoholic metabolites of pentobarbital and amobarbital in man". The Journal of Pharmacology and Experimental Therapeutics 150 (1): 118–121. PMID 5855308.

[5] Tang, B. K.; Kalow, W.; Grey, A. A. (1978). "Amobarbital metabolism in man: N-glucoside formation". Research communications in chemical pathology and pharmacology 21 (1): 45–53. PMID 684279.

[6] Soine, P. J.; Soine, W. H. (1987). "High-performance liquid chromatographic determination of the diastereomers of 1-(beta-D-glucopyranosyl)amobarbital in urine". Journal of chromatography 422: 309–314. doi:10.1016/0378-4347(87)80468-1. PMID 3437019.

[7] Bleckwenn, W. J. (1930). "Sodium amytal in certain nervous and mental conditions". Wisconsin Medical Journal 29: 693–696.

[Stocks-8] Stocks, J. T. (1998). "Recovered memory therapy: A dubious practice technique". Social work 43 (5): 423–436. doi:10.1093/sw/43.5.423. PMID 9739631.

[9] McCall, W. V. (1992). "The addition of intravenous caffeine during an amobarbital interview". Journal of psychiatry & neuroscience : JPN 17 (5): 195–197. PMC 1188455. PMID 1489761.

[10] "Use of sodium amytal during WWII". Battle of the Bulge - program transcript. PBS. 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.

[11] GB patent 191008, Layraud, E., "The manufacture of unsymmetrical c.c.-dialkylbarbituric acids", issued 1923-10-25

[12] US patent 1856792, Shonle, H. A., "Anhydrous alkali salts of 5,5-di-aliphatic-substituted barbituric acids and processes of producing them", issued 1932-05-03

[CBS-13] Rebecca Leung (February 11, 2009). "Truth Serum: A Possible Weapon". 60 Minutes. CBS News.

匿名

検索

案内

案内

amylobarbitone