Sodium thiopental

Sodium thiopental, also known as Sodium Pentothal (a trademark of Abbott Laboratories), thiopental, thiopentone, or Trapanal (also a trademark), is a rapid-onset short-acting barbiturate general anesthetic. It is the thiobarbiturate analog of pentobarbital, and an analog of thiobarbital. Sodium thiopental was a core medicine in the World Health Organization's List of Essential Medicines, but was supplanted by propofol. Despite this, thiopental is listed as an acceptable alternative to propofol, depending on local availability and cost of these agents. It was previously the first of three drugs administered during most lethal injections in the United States, but the US manufacturer Hospira stopped manufacturing the drug in 2011 and the European Union banned the export of the drug for this purpose. Although thiopental abuse carries a dependency risk, its recreational use is rare.

Not to be confused with pentobarbital or phenobarbital.
"Sodium Pentathol" and "C11 H17 N2 O2 S Na" redirect here. For the song by Anthrax, see Sound of White Noise.
Sodium thiopental
Clinical data
Trade namesPentothal, Trapanal
Other namesTruth serum, thiopentone, thiopental
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: D
Routes of
administration		Intravenous (most common), oral, or rectal
Drug classBarbiturate
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding80%
MetabolismLiver
MetabolitesPentobarbital, others
Onset of action30–45 seconds
Elimination half-life5.5–26 hours
Duration of action5–10 minutes
Identifiers
  • sodium 5-ethyl-5-pentan-2-yl-2-sulfanylidene-1,3-diazinane-4,6-dione
CAS Number
  • 71-73-8 Y (sodium salt)
    76-75-5 (free acid)
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.694
Chemical and physical data
FormulaC11H17N2NaO2S
Molar mass264.32 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • [Na+].O=C1NC(=S)/N=C(/[O-])C1(C(C)CCC)CC
  • InChI=1S/C11H18N2O2S.Na/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15;/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16);/q;+1/p-1 Y
  • Key:AWLILQARPMWUHA-UHFFFAOYSA-M Y
 NY (what is this?)  (verify)
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