Amobarbital

Drugbox
IUPAC_name = "5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione"

---

width = 150
CAS_number = 57-43-2
ChemSpiderID = 2079
CAS_supplemental = 64-43-7 (sodium salt)
ATC_prefix = N05
ATC_suffix = CA02
ATC_supplemental =
PubChem = 2164
smiles = C1(C(N(C(N(C1=O) [H] )=O) [H] )=O)(CCC(C)C)CC
DrugBank = none
chemical_formula =
C = 11 | H = 18 | N = 2 | O = 3
molecular_weight = 226.272
bioavailability = ?
metabolism = Hepatic
elimination_half-life = 8-42 hours
excretion = Renal
pregnancy_category = ?
legal_US =
legal_CA = Schedule IV
legal_status = Schedule II/Schedule III (US)
routes_of_administration = Oral, IM, IV, Rectal

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.

Pharmacology

According to an "in vitro" study conducted at the University of British Columbia, amobarbital works by activating GABA_A receptors, which decreases input resistance, depresses 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 increases both the amplitude and decay time of postsynaptic currents.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]

It has an LD₅₀ in mice of 212 mg/kg s.c.

Metabolism

Amobarbital undergoes both hydroxylation to form 3'-hydroxyamobarbital,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] which has both levorotatory and dextrorotatory isomers [http://ctd.mdibl.org/voc.go?voc=chem&termUI=3'-hydroxyamobarbital Chemicals: 3'-hydroxyamobarbital] The Comparative Toxicology Database.] and N-glucosidationTang 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] to form 1-(beta-D-glucopyranosyl)amobarbital.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]

Indications

Approved

* Anxiety
* Insomnia
* Epilepsy

Unapproved/Off-Label

* 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 alleged 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. [http://www.cbsnews.com/stories/2003/04/07/60II/main548221.shtml Truth Serum: A Possible Weapon] , "60 Minutes", April 23, 2003.] 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.Fact|date=March 2007

* Catatonic mutism, sometimes combined with caffeine to combat somnolence.McCall WV. "The addition of intravenous caffeine during an amobarbital interview." "Journal of Psychiatry & Neuroscience." 1992 Nov;17(5):195-7. PMID 1489761]

* It was also used in the Battle of the Bulge as a healing pill to send people back to the front. [ [http://www.pbs.org/wgbh/amex/bulge/filmmore/pt.html Use of sodium amytal during WWII] ]

Contraindications

The following drugs should be avoided when taking amobarbital:
* Alcohol
* CaffeineFact|date=February 2007
* 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 Fact|date=February 2007
* Antihypertensives, such as atenolol and propranolol
* Antiarrhythmics, such as verapamil and digoxin

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.

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).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 | doi=10.1007/BF00216067 PMID 2906155]

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). Death can be a result, as in the case of the Hollywood actor, Robert Walker.

ee also

* Depressants
* Barbiturates
* Wada test

References and End Notes

# [http://www.deadiversion.usdoj.gov/schedules/listby_sched/sched2.htm Controlled Substances in Schedule II] Office of Diversion Control, Drug Enforcement Administration.
# [http://www.deadiversion.usdoj.gov/schedules/listby_sched/sched3.htm Controlled Substances in Schedule III] Office of Diversion Control, Drug Enforcement Administration.

External links