amobarbital

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Brand names: Amytal®

Chemical formula:

Espa�ol:
• Inyección de amobarbital

Amobarbital injection

What does amobarbital injection do?

AMOBARBITAL (Amytal®) is a barbiturate that slows down activity of the brain and nervous system. Amobarbital has both sedative and hypnotic properties which means it will help you to relax and sleep. Amobarbital can help produce relaxation and drowsiness before surgery. Amobarbital also can help reduce or control seizures (convulsions). It is not for the long-term control or prevention of seizures. Federal law prohibits the transfer of amobarbital to any person other than the patient for whom it was prescribed. Do not share your medicine with anyone else. Generic amobarbital injections are available.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
• an alcohol or drug abuse problem
• breathing difficulties or lung disease
• attempted suicide
• heart disease
• liver disease
• low blood pressure
• mental depression or mental problems
• porphyria
• an unusual or allergic reaction to amobarbital, other barbiturates, medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should I use this medicine?

Amobarbital is for injection into a muscle or into a vein. It is given by a health-care professional in a hospital or clinic setting.

Contact your pediatrician or health care professional regarding the use of this medicine in children. Special care may be needed.

Elderly patients over age 65 years may have a stronger reaction to this medicine and need smaller doses.

What if I miss a dose?

What drug(s) may interact with amobarbital?

• alcohol
• caffeine
• chloramphenicol
• chlorpromazine
• cyclophosphamide
• cyclosporine
• digitoxin
• doxorubicin
• doxycycline
• female hormones, including contraceptive or birth control pills
• methoxyflurane
• metronidazole
• medicines for anxiety or sleeping problems
• medicines for hay fever and other allergies
• medicines for high blood pressure
• medicines for mental depression
• medicines for pain
• medicines that help the heart to beat regularly
• quinine
• seizure (convulsion) or epilepsy medicine
• steroid medicines such as prednisone or cortisone
• theophylline
• warfarin

Tell your prescriber or health care professional about all other medicines you are taking, including non-prescription medicines, nutritional supplements, or herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.

What should I watch for while taking amobarbital?

Your condition will be monitored closely if you are receiving amobarbital for an immediate need. If you do receive amobarbital regularly, visit your prescriber or health care professional for regular checks on your progress.

After receiving amobarbital you may get a residual hangover effect that leaves you drowsy or dizzy. Do not drive, use machinery, or do anything that needs mental alertness until you know how amobarbital affects you. To reduce dizzy or fainting spells, do not sit or stand up quickly, especially if you are an older patient. Alcohol can increase possible unpleasant effects. Avoid alcoholic drinks.

Amobarbital can stop birth control pills (oral contraceptives) working properly. Use another method of birth control while you are using amobarbital.

If you are going to have surgery, tell your prescriber or health care professional that you are receiving amobarbital.

What side effects may I notice from receiving amobarbital?

Side effects that you should report to your prescriber or health care professional as soon as possible:
• bone tenderness
• confusion, agitation, changes in mood, or mental ability
• depression
• eye problems, very small or enlarged centers to the eyes
• lightheadedness, fainting spells
• fever, sore throat
• hallucinations
• redness, blistering, peeling or loosening of the skin, including inside the mouth
• shortness of breath, or difficulty breathing
• skin rash, itching, hives
• slow heartbeat
• swelling of the face or lips
• unusual bleeding or bruising; pinpoint red spots on the skin
• unusual tiredness or weakness
• weight loss
• yellowing of skin or eyes

Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
• clumsiness, unsteadiness, or a "hangover" effect
• constipation
• difficulty sleeping or nightmares
• drowsiness, dizziness
• headache
• irritability, nervousness
• nausea or vomiting
• pain, redness or irritation at the injection site

Where can I keep my medicine?

Keep out of the reach of children.

Use the injection solution within 30 minutes of preparation. Do not use the solution unless quite clear. Throw away any unused medicine after the expiration date.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

• PHARMACOLOGY - amobarbital: moderate hypnotic barbiturate

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 cat.	?
Legal status	Schedule IV (CA) Schedule II/Schedule III (US)
Routes	Oral, IM, IV, Rectal
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Half-life	8-42 hours
Excretion	Renal
Identifiers
CAS number	57-43-2 Y 64-43-7 (sodium salt)
ATC code	N05CA02
PubChem	CID 2164
DrugBank	DB01351
ChemSpider	2079 Y
UNII	GWH6IJ239E Y
KEGG	D00555 Y
ChEBI	CHEBI:2673 Y
ChEMBL	CHEMBL267894 Y
Chemical data
Formula	C11H18N2O3
Mol. mass	226.272
SMILES	eMolecules & PubChem
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) Y Key:VIROVYVQCGLCII-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

Amobarbital (formerly known as amylobarbitone) 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.

Contents 1 Pharmacology 2 Metabolism 3 Indications 3.1 Approved 3.2 Unapproved/off-label 4 Contraindications 5 Interactions 6 Overdose 7 Chemistry 8 Trivia 9 See also 10 References and end notes 11 External links

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
• Insomnia
• Epilepsy
• 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. A person under the influence of the drug in this circumstance will relate information that he or she would otherwise "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]

Contraindications

A vial of amytal sodium

The following drugs should be avoided when taking amobarbital:

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

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).

• 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 

Trivia

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.^[11]

See also

• Depressants
• Barbiturates
• Wada test
• Blue 88

References and end notes

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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1575418.  edit
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.  edit
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.  edit
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.  edit
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.  edit
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. PMID 3437019.  edit
7. ^ Bleckwenn, W. J. (1930). "Sodium amytal in certain nervous and mental conditions". Wisconsin Medical Journal 29: 693–696. 
8. ^ Stocks, J. T. (1998). "Recovered memory therapy: A dubious practice technique". Social work 43 (5): 423–436. PMID 9739631.  edit
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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1188455.  edit
10. ^ "Use of sodium amytal during WWII". Battle of the Bulge - program transcipt. pbs.org. http://www.pbs.org/wgbh/amex/bulge/filmmore/pt.html. "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 88's, because the sodium amytal was a blue tablet." 
11. ^ Rebecca Leung (February 11, 2009). "Truth Serum: A Possible Weapon". 60 Minutes. CBS News. http://www.cbsnews.com/stories/2003/04/07/60II/main548221.shtml. 

External links

v t e GABAA receptor PAMs Barbiturates Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Bucolome Butabarbital Butalbital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopal Difebarbamate Enallylpropymal Ethallobarbital Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenobarbital Phetharbital Primidone Prazitone Probarbital Propallylonal Proxibarbal Proxibarbital Reposal Secbutabarbital Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Valofane Vinbarbital Vinylbital Benzodiazepines Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Chlordiazepoxide Ciclotizolam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Cyprazepam Delorazepam Diazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Girisopam Halazepam Haloxazolam Iclazepam Imidazenil Ketazolam Lofendazam Lopirazepam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Nerisopam Nimetazepam Nitrazepam Nitrazepate Nordazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tofisopam Triazolam Triflubazam Uldazepam Zapizolam Zolazepam Zomebazam Carbamates Carisbamate Carisoprodol Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Methocarbamol Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate Neuroactive steroids Acebrochol Allopregnanolone Alphadolone Alphaxolone Ganaxolone Hydroxydione Minaxolone Org 20599 THDOC Nonbenzodiazepines β-Carbolines: Abecarnil Gedocarnil SL-651,498 ZK-93423; Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone; Imidazopyridines: Alpidem Necopidem Saripidem Zolpidem; Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon; Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 ELB-139 GBLD-345 L-838,417 NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TP-003 TPA-023 TP-13 U-89843A U-90042 Y-23684 Phenols Fospropofol Propofol Thymol Piperidinediones Glutethimide Methyprylon Piperidione Pyrithyldione Pyrazolopyridines Cartazolate Etazolate ICI-190,622 Tracazolate Quinazolinones Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Volatiles/gases 2-Methyl-2-butanol Acetone Acetophenone Acetylglycinamide chloral hydrate Benzene Butane Butanol Butylene Centalun Chloral Chloral hydrate Chlorobutanol Chloroform Cyclopropane Desflurane Dichloromethane Diethyl ether Enflurane Ethanol (Alcohol) Ethyl chloride Ethylene Gasoline Halothane Isoflurane Kerosine Menthol Methanol Methoxyflurane Methoxypropane Methylbutanol Nitric oxide Nitrogen Nitrous oxide Paraldehyde Pentanol Propane Propanol Propylene Sevoflurane Toluene Trichloroethanol Trichloroethylene Vinyl ether Xenon Others Bromide (Lithium bromide Potassium bromide Sodium bromide) Chloralodol Chloralose Chlormezanone Clomethiazole DEABL Etazepine Ethchlorvynol Etifoxine Etomidate GABA Kavalactones (Kava) Loreclezole Methylpentynol Metomidate Org 25,435 Petrichloral Propanidid Skullcap Stiripentol Sulfonmethane Tetronal Triclofos Trional Valeric acid Valerenic acid (Valerian)

v t e Hypnotics/sedatives (N05C) GABAA agonists/PAMs Barbiturates: Allobarbital • Amobarbital • Aprobarbital • Barbital • Butabarbital • Butobarbital • Cyclobarbital • Ethallobarbital • Heptabarb • Hexobarbital • Mephobarbital • Methohexital • Pentobarbital • Phenobarbital • Proxibarbal • Reposal • Secobarbital • Talbutal • Thiamylal • Thiopental • Vinbarbital • Vinylbital Benzodiazepines: Brotizolam • Clonazepam • Cinolazepam • Climazolam • Doxefazepam • Estazolam • Flunitrazepam • Flurazepam • Flutoprazepam • Haloxazolam • Loprazolam • Lorazepam •Lormetazepam • Midazolam • Nimetazepam • Nitrazepam • Quazepam • Temazepam • Triazolam Carbamates: Carisoprodol • Ethinamate • Hexapropymate • Meprobamate • Methocarbamol • Procymate • Tybamate Neuroactive Steroids: Acebrochol • Allopregnanolone • Alphadolone • Alphaxolone • Eltanolone • Ganaxolone • Hydroxydione • Minaxolone • Org 20599 • Org 21465 • Tetrahydrodeoxycorticosterone Nonbenzodiazepines: CL-218,872 • Eszopiclone • Indiplon • JM-1232 • Lirequinil • Necopidem • Pazinaclone • ROD-188 • Saripidem • Suproclone • Suriclone • SX-3228 • U-89843A • U-90042 • Zaleplon • Zolpidem • Zopiclone Phenols: Fospropofol • Propofol Piperidinediones: Glutethimide • Methyprylon • Pyrithyldione • Piperidione Quinazolinones: Afloqualone • Cloroqualone • Diproqualone • Etaqualone • Mebroqualone • Mecloqualone • Methaqualone • Methylmethaqualone • Nitromethaqualone Volatiles/gases: 2-Methyl-2-butanol • Acetophenone • Acetylglycinamide chloral hydrate • Centalun • Chloral hydrate • Ethanol (Alcohol) • Paraldehyde • Trichloroethanol Others: Bromide (Lithium bromide, Potassium bromide, Sodium bromide) • Chloralose • Chloralodol • Clomethiazole • Dichloralphenazone • Ethchlorvynol • Etomidate • Gaboxadol • Loreclezole • Methylpentynol • Metomidate • Org 25435 • Petrichloral • Sulfonmethane • Triclofos • Valerenic acid (Valerian) GABAB agonists 1,4-Butanediol • Aceburic acid • GABOB • GHB (Sodium oxybate) • GBL • GVL H1 inverse agonists Antihistamines: Captodiame • Cyproheptadine • Diphenhydramine • Doxylamine • Hydroxyzine • Methapyrilene • Pheniramine • Promethazine • Propiomazine Antidepressants: Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc.) Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.) α1-Adrenergic antagonists Antidepressants: Serotonin antagonists and reuptake inhibitors (Trazodone) • Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin) Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.) Others: Niaprazine α2-Adrenergic agonists 4-NEMD • Clonidine • Detomidine • Dexmedetomidine • Lofexidine • Medetomidine • Romifidine • Tizanidine • Xylazine 5-HT2A antagonists Antidepressants: Serotonin antagonists and reuptake inhibitors (Trazodone) • Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc.) Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.) Others: Eplivanserin • Niaprazine • Pruvanserin • Volinanserin Melatonin agonists Agomelatine • LY-156,735 • Melatonin • Ramelteon • Tasimelteon Orexin antagonists Almorexant • SB-334,867 • SB-408,124 • SB-649,868 • Suvorexant • TCS-OX2-29 Others Acecarbromal • Apronal • Bromisoval • Cannabidiol (Cannabis) • Carbromal • Embutramide • Evoxine • Fenadiazole • Gabapentin • Kavalactones (Kava) • Mephenoxalone • Opioids (Oxycodone, Morphine (Opium), etc.) • Passion flower • Scopolamine (Mandrake) • Valnoctamide

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