Hexobarbital

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Hexobarbital
Clinical data
Trade namesEvipan, others
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding25%
Identifiers
  • (RS)-5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.241 Edit this at Wikidata
Chemical and physical data
FormulaC12H16N2O3
Molar mass236.271 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Melting point146.5 °C (295.7 °F)
Solubility in water0.435 mg/mL (20 °C)
  • O=C1N(C(=O)NC(=O)C1(/C2=C/CCCC2)C)C
  • InChI=1S/C12H16N2O3/c1-12(8-6-4-3-5-7-8)9(15)13-11(17)14(2)10(12)16/h6H,3-5,7H2,1-2H3,(H,13,15,17) checkY
  • Key:UYXAWHWODHRRMR-UHFFFAOYSA-N checkY
  (verify)

Hexobarbital or hexobarbitone, sold both in acid and sodium salt forms as Citopan, Evipan, and Tobinal, is a barbiturate derivative having hypnotic and sedative effects. It was used in the 1940s and 1950s as an agent for inducing anesthesia for surgery, as well as a rapid-acting, short-lasting hypnotic for general use, and has a relatively fast onset of effects and short duration of action.[1] It was also used to murder women prisoners at Ravensbruck Concentration Camp.[2] Modern barbiturates (such as Thiopental) have largely supplanted the use of hexobarbital as an anesthetic, as they allow for better control of the depth of anesthesia.[3] Hexobarbital is still used in some scientific research.[4]

Chemistry

Hexobarbital is a racemic white powder with a bitter taste.[5] It melts at 146.5 °C and has a dissociation constant of 8.2.[6]

In popular culture

In Agatha Christie's 1937 mystery Cards on the Table, Hexobarbital is used in conjunction with Veronal to induce overdose. It is referred to by Hercule Poirot as both N-methyl-cyclo-hexenyl-methyl-malonyl urea and Evipan.[7]

References

  1. ^ Lexikon der Neurowissenschaft: Hexobarbital (in German)
  2. ^ Helm, Sarah (2015). If this is a woman: Inside Ravensbruck: Hitler’s concentration camp for women. London: Abacus. pp. 243–258. ISBN 9780349120034. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  3. ^ Pubchem. "Hexobarbital | C12H16N2O3 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-05-02.
  4. ^ Tseilikman VE, Kozochkin DA, Manukhina EB, Downey HF, Tseilikman OB, Misharina ME, et al. (April 2016). "Duration of hexobarbital-induced sleep and monoamine oxidase activities in rat brain: Focus on the behavioral activity and on the free-radical oxidation". General Physiology and Biophysics. 35 (2): 175–83. doi:10.4149/gpb_2015039. PMID 26689857.
  5. ^ "Hexobarbital". Vetpharm. Retrieved 18 February 2016.
  6. ^ Template:ChemID.
  7. ^ Christie, Agatha (1937). Cards on the Table. New York: William Morrow. p. 242. ISBN 978-0-06-207373-0.

Further reading