Hexobarbital

Hexobarbital
Clinical data
Trade names	Hexobarbital, Hexobarbitone, Methylhexabital, Methexenyl, Evipal
ATC code	N01AF02 (WHO) N05CA16 (WHO);
Legal status
Legal status	CA: Schedule IV; US: Schedule III;
Pharmacokinetic data
Protein binding	25%
Identifiers
	IUPAC name 5-(cyclohex-1-en-1-yl)-1,5-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione;
CAS Number	56-29-1 ; 50-09-9 (sodium salt);
PubChem CID	3608;
DrugBank	DB01355 ;
ChemSpider	3482 ;
UNII	AL8Z8K3P6S;
KEGG	D01071 ;
ChEBI	CHEBI:5706 ;
ChEMBL	ChEMBL7728 ;
CompTox Dashboard (EPA)	DTXSID9023122 ;
ECHA InfoCard	100.000.241
Chemical and physical data
Formula	C12H16N2O3
Molar mass	236.271 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
Density	1.1623 g/cm3
Melting point	146.5 °C (295.7 °F)
Boiling point	378.73 °C (713.71 °F)
Solubility in water	0.435 mg/mL (20 °C)
	SMILES O=C1N(C(=O)NC(=O)C1(/C2=C/CCCC2)C)C;
	InChI 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) ; Key:UYXAWHWODHRRMR-UHFFFAOYSA-N ;
	(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] 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.^[2] Hexobarbital is still used in some scientific research.^[3]

^ Lexikon der Neurowissenschaft: Hexobarbital (in German)
^ Pubchem. "Hexobarbital | C12H16N2O3 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-05-02.
^ Tseilikman VE, Kozochkin DA, Manukhina EB, Downey HF, Tseilikman OB, Misharina ME, Nikitina AA, Komelkova MV, Lapshin MS, Kondashevskaya MV, Lazuko SS, Kusina OV, Sahabutdinov MV (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.

[1] Lexikon der Neurowissenschaft: Hexobarbital (in German)

[2] Pubchem. "Hexobarbital | C12H16N2O3 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-05-02.

[3] Tseilikman VE, Kozochkin DA, Manukhina EB, Downey HF, Tseilikman OB, Misharina ME, Nikitina AA, Komelkova MV, Lapshin MS, Kondashevskaya MV, Lazuko SS, Kusina OV, Sahabutdinov MV (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.

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