Amobarbital

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 none
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
 N(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

Pharmacology

In an in vitro study in rat thalamic slices amobarbital worked by activating GABAA 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.

Metabolism

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

Indications

Approved

Unapproved/off-label

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]

Contraindications

The following drugs should be avoided when taking amobarbital:

Interactions

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.

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).

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

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. 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