From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Hexobarbital ball-and-stick.png
Clinical data
Trade namesEvipan, others
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding25%
CAS Number
PubChem CID
CompTox Dashboard (EPA)
ECHA InfoCard100.000.241 Edit this at Wikidata
Chemical and physical data
Molar mass236.267 g/mol g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Melting point146.5 °C (295.7 °F)
Solubility in water0.435 mg/mL (20 °C)

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]


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]


  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.
  3. ^ Pubchem. "Hexobarbital | C12H16N2O3 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-05-02.
  4. ^ 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. 35 (2): 175–83. doi:10.4149/gpb_2015039. PMID 26689857.
  5. ^ "Hexobarbital". Vetpharm. Retrieved 18 February 2016.
  6. ^ Hexobarbital in the ChemIDplus database.

Further reading[edit]