Sodium thiopental

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), by mouth, 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[2]–26 hours[3]
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 checkY (sodium salt)
    76-75-5 (free acid)
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.694 Edit this at Wikidata
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 checkY
  • Key:AWLILQARPMWUHA-UHFFFAOYSA-M checkY
 ☒NcheckY (what is this?)  (verify)
Pentothal vintage package

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,[4] but was supplanted by propofol.[5][6][7] Despite this, thiopental is listed as an acceptable alternative to propofol, depending on local availability and cost of these agents.[7] It was the first of three drugs administered during most lethal injections in the United States until the US division of Hospira objected and stopped manufacturing the drug in 2011, and the European Union banned the export of the drug for this purpose.[8] Although thiopental abuse carries a dependency risk, its recreational use is rare.[9]

Sodium thiopental is well-known in popular culture, especially under the name "sodium pentothal," as a "truth serum," although its efficacy in this role has been questioned.[10][11]

  1. ^ Anvisa (2023-03-31). "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 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Russo H, Brès J, Duboin MP, Roquefeuil B (1995). "Pharmacokinetics of thiopental after single and multiple intravenous doses in critical care patients". European Journal of Clinical Pharmacology. 49 (1–2): 127–37. doi:10.1007/BF00192371. PMID 8751034. S2CID 24285007.
  3. ^ Morgan DJ, Blackman GL, Paull JD, Wolf LJ (June 1981). "Pharmacokinetics and plasma binding of thiopental. II: Studies at cesarean section". Anesthesiology. 54 (6): 474–80. doi:10.1097/00000542-198106000-00006. PMID 7235275.
  4. ^ World Health Organization (2009). WHO Model List of Essential Medicines 16th list, March 2009. Geneva, Switzerland: World Health Organization. hdl:10665/70642/.
  5. ^ World Health Organization (2012). The selection and use of essential medicines : report of the WHO Expert Committee, March 2011 (including the 17th WHO model list of essential medicines and the 3rd WHO model list of essential medicines for children). Geneva: World Health Organization. hdl:10665/44771. ISBN 9789241209656. ISSN 0512-3054. WHO technical report series; 965.
  6. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  7. ^ a b World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  8. ^ "Death Penalty Opposition: EU Set to Ban Export of Drug Used in US Executions". Spiegel Online International. Retrieved 23 January 2014.
  9. ^ Bryson EO (December 2014). "The Abuse of Agents Used to Induce or Maintain General Anesthesia: Intravenous Hypnotics and the Halogenated Hydrocarbons". In Kaye AD, Vadivelu N, Urman RD (eds.). Substance abuse: inpatient and outpatient management for every clinician. New York: Springer. p. 115. doi:10.1007/978-1-4939-1951-2_10. ISBN 978-1493919512. OCLC 897466425.
  10. ^ "Can a drug make you tell the truth?". BBC News. 2013-10-03. Retrieved 2024-05-19.
  11. ^ Orwig J. "'Truth serum' drugs do exist. Here's how medicines like sodium pentothal and scopolamine can manipulate the brain". Business Insider. Retrieved 2024-05-19.