Hexobarbital

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Hexobarbital
Hexobarbital.png
Hexobarbital ball-and-stick.png
Clinical data
Trade names Citopan, Evipan, Tobinal
ATC code N01AF02 (WHO) N05CA16 (WHO)
Legal status
Legal status
Pharmacokinetic data
Protein binding 25%
Identifiers
CAS Number 56-29-1 YesY
50-09-9 (sodium salt)
PubChem (CID) 3608
DrugBank DB01355 YesY
ChemSpider 3482 YesY
UNII AL8Z8K3P6S YesY
KEGG D01071 YesY
ChEBI CHEBI:5706 YesY
ChEMBL CHEMBL7728 YesY
ECHA InfoCard 100.000.241
Chemical and physical data
Formula C12H16N2O3
Molar mass 236.267 g/mol
3D model (Jmol) Interactive image
Chirality Racemic mixture
Melting point 146.5 °C (295.7 °F)
Solubility in water 0.435 mg/mL (20 °C)
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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] Modern barbiturates (such as Thiopental) has largely supplanted the use of hexobarbital as an anesthetic, as they allow for better control of the depth of anesthesia.[2] Hexobarbital is still used in some scientific research.[3]

Chemistry[edit]

Hexobarbital is a racemic white powder with a bitter taste.[4] It melts at 146.5 °C and has a dissociation constant of 8.2.[5]

References[edit]

  1. ^ Lexikon der Neurowissenschaft: Hexobarbital (German)
  2. ^ Pubchem. "Hexobarbital | C12H16N2O3 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-05-02. 
  3. ^ Tseilikman, V. E.; Kozochkin, D. A.; Manukhina, E. B.; Downey, H. F.; Tseilikman, O. B.; Misharina, M. E.; Nikitina, A. A.; Komelkova, M. V.; Lapshin, M. S.; Kondashevskaya, M. V.; Lazuko, S. S.; Kusina, O. V.; Sahabutdinov, M. V. (2015). "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. doi:10.4149/gpb_2015039 (inactive 2016-02-18). PMID 26689857. 
  4. ^ "Hexobarbital". Vetpharm. Retrieved 18 February 2016. 
  5. ^ Hexobarbital in the ChemIDplus database.

Further reading[edit]