Thiobarbital

Thiobarbital

Systematic (IUPAC) name
5,5-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
Clinical data
Pregnancy category	?
Routes of administration	?
Legal status	?
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Biological half-life	?
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Identifiers
CAS Number	77-32-7
ATC code	?? (WHO)
PubChem	CID 667509
DrugBank	?
ChemSpider	580885
Chemical data
Formula	C8H12N2O2S
Molar mass	200.259
SMILES O=C1NC(=S)NC(=O)C1(CC)CC
InChI InChI=1S/C8H12N2O2S/c1-3-8(4-2)5(11)9-7(13)10-6(8)12/h3-4H2,1-2H3,(H2,9,10,11,12,13) Key:QGVNJRROSLYGKF-UHFFFAOYSA-N
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Thiobarbital is a drug which is a barbiturate derivative. It is the thiobarbiturate analogue of barbital.

Synthesis

Thiobarbital synthesis:^[1][2]

It is of note that although the drug can be prepared by the above route (cf eg thialbarbital), rxn of barbital with phosphorus pentasulfide constitutes an alternative route to thiobarbital.

References

1. Fischer, E.; Dilthey, A. (1904). "Ueber C-Dialkylbarbitursäuren und über die Ureïde der Dialkylessigsäuren". Justus Liebig's Annalen der Chemie 335 (3): 334. doi:10.1002/jlac.19043350303.
2. Carrington, H. C. (1944). "45. The action of phosphorus pentasulphide on barbituric acids". Journal of the Chemical Society (Resumed): 124. doi:10.1039/JR9440000124.