Hexobarbital
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| Systematic (IUPAC) name | |
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(RS)-5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
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| Clinical data | |
| Trade names | Citopan, Evipan, Tobinal |
| Legal status | |
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| Pharmacokinetic data | |
| Protein binding | 25% |
| Identifiers | |
| CAS Number | 56-29-1  50-09-9 (sodium salt) |
| ATC code | N01AF02 (WHO) N05CA16 (WHO) |
| PubChem | CID 3608 |
| DrugBank | DB01355 |
| ChemSpider | 3482 |
| UNII | AL8Z8K3P6S |
| KEGG | D01071 |
| ChEBI | CHEBI:5706 |
| ChEMBL | CHEMBL7728 |
| Chemical data | |
| Formula | C12H16N2O3 |
| Molar mass | 236.267 g/mol |
| Chirality | Racemic mixture |
| 3D model (Jmol) | Interactive image |
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| Physical data | |
| 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]
- ^ Lexikon der Neurowissenschaft: Hexobarbital (German)
- ^ Pubchem. "Hexobarbital | C12H16N2O3 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-05-02.
- ^ 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.
- ^ "Hexobarbital". Vetpharm. Retrieved 18 February 2016.
- ^ Hexobarbital in the ChemIDplus database.
Further reading[edit]
- Takenoshita, R.; Toki, S. (2004). "New aspects of hexobarbital metabolism: Stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases" (pdf). Yakugaku Zasshi (in Japanese). 124 (12): 857–871. doi:10.1248/yakushi.124.857. PMID 15577260.
- Wahlström, G. (1998). "A study of the duration of acute tolerance induced with hexobarbital in male rats". Pharmacology, Biochemistry, and Behavior. 59 (4): 945–948. doi:10.1016/S0091-3057(97)00543-1. PMID 9586853.
- Korkmaz, S.; Ljungblad, E.; Wahlström, G. (1995). "Interaction between flumazenil and the anesthetic effects of hexobarbital in the rat". Brain Research. 676 (2): 371–377. doi:10.1016/0006-8993(95)00132-A. PMID 7614008.
- Dall, V.; Orntoft, U.; Schmidt, A.; Nordholm, L. (1993). "Interaction of the competitive AMPA receptor antagonist NBQX with hexobarbital". Pharmacology, Biochemistry, and Behavior. 46 (1): 73–76. doi:10.1016/0091-3057(93)90319-O. PMID 8255925.
