Butabarbital

Butabarbital
Clinical data
Trade names	Butisol
AHFS/Drugs.com	Professional Drug Facts
MedlinePlus	a682417
License data	US DailyMed: Butabarbital;
ATC code	none;
Legal status
Legal status	BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: Anlage II (Authorized trade only, not prescriptible); US: Schedule III;
Pharmacokinetic data
Elimination half-life	100 hours
Excretion	Urine
Identifiers
	IUPAC name 5-butan-2-yl-5-ethyl-1,3-diazinane-2,4,6-trione;
CAS Number	125-40-6 ;
PubChem CID	2479;
IUPHAR/BPS	7137;
DrugBank	DB00237 ;
ChemSpider	2385 ;
UNII	P0078O25A9;
KEGG	D03180 ;
ChEBI	CHEBI:3228 ;
ChEMBL	ChEMBL449 ;
CompTox Dashboard (EPA)	DTXSID2022709 ;
ECHA InfoCard	100.004.308
Chemical and physical data
Formula	C10H16N2O3
Molar mass	212.249 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1NC(=O)NC(=O)C1(C(C)CC)CC;
	InChI InChI=1S/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15) ; Key:ZRIHAIZYIMGOAB-UHFFFAOYSA-N ;
	(verify)

Butabarbital (brand name Butisol) is a prescription barbiturate sleep aid and anxiety medication. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia, relieving general anxiety and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its intermediate duration of action gives butabarbital an abuse potential slightly lower than secobarbital. Butabarbital can be hydrolyzed to valnoctamide.^[4]

Stereoisomeres of butabarbital

(R)-Stereoisomer	(S)-Stereoisomer

Butabarbital is also sold in combination with belladonna alkaloids under the brand name Butibel. The belladonna is added for antispasmodic effect. This product contains a low dose of butabarbital combined with a standardised mix of belladonna alkaloids and is used as an antispasmodic taken to relieve cramping and spasms of the stomach and intestines. They are used also to decrease the amount of acid formed in the stomach. Another similar product is Donnatal, which contains belladonna alkaloids combined with phenobarbital.

^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
^ "Butisol". RxList. Archived from the original on 6 June 2011. Retrieved 11 March 2010.
^ Maynert EW, Losin L (November 1955). "The metabolism of butabarbital (butisol) in the dog". The Journal of Pharmacology and Experimental Therapeutics. 115 (3): 275–82. PMID 13272177.
^ Freifelder M, Geiszler AO, Stone GR (1961). "Hydrolysis of 5,5-Disubstituted Barbituric Acids". The Journal of Organic Chemistry. 26 (1): 203–206. doi:10.1021/jo01060a048.

[1] Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.

[2] "Butisol". RxList. Archived from the original on 6 June 2011. Retrieved 11 March 2010.

[Maynert_1955-3] Maynert EW, Losin L (November 1955). "The metabolism of butabarbital (butisol) in the dog". The Journal of Pharmacology and Experimental Therapeutics. 115 (3): 275–82. PMID 13272177.

[FreifelderGeiszler1961-4] Freifelder M, Geiszler AO, Stone GR (1961). "Hydrolysis of 5,5-Disubstituted Barbituric Acids". The Journal of Organic Chemistry. 26 (1): 203–206. doi:10.1021/jo01060a048.

[1]

[2]

[3]

[4]