Thiopental
5-ethyl-5-pentan-2-yl-2-sulfanylidene-1,3-diazinane-4,6-dione
Overview
Thiopental belongs to Depressants.
Effects
- Given IV: near-instant drowsiness with a metallic/garlic taste, then loss of consciousness within seconds.
- Deep anaesthesia with slowed or absent breathing and lowered blood pressure.
- Rapid awakening after a single dose (minutes) as it redistributes, often with residual grogginess. Prolonged sedation after repeated dosing.
Dosing & duration
Intravenous only, administered by an anaesthetist. Figures below are clinical context, NOT a recreational guide.. Thiopental is titrated intravenously to loss of consciousness by clinicians equipped to manage apnoea and hypotension. There is no safe non-medical use. Its brief action after a single dose is due to redistribution, so repeated boluses or infusions accumulate and prolong recovery unpredictably.
Dose ranges
≈3–5 mg/kg, titrated
IV loading + infusion, specialist-titrated to EEG
Duration
IV ≈30–45 s
Single dose ≈5–10 min (redistribution)
Residual sedation. Markedly prolonged after repeated/continuous dosing
Chemical & Physical Properties
| Formula | C11H18N2O2S |
| Molar mass | 242.34 g/mol |
| State | Solid |
| Melting point | Not reported |
| Boiling point | Not reported |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | 7.55 |
| LogP | 2.85 |
| Solubility | 3.98×10⁻² g/L |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 76-75-5 |
| CAS (enantiomer) | |
| PubChem CID | 3000715 |
| InChIKey | IUJDSEJGGMCXSG-UHFFFAOYSA-N |
| InChI | InChI=1S/C11H18N2O2S/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) |
| SMILES | CCCC(C)C1(C(=O)NC(=S)NC1=O)CC |
Synonyms
- Sodium thiopental
- Thiopentone
- Pentothal
- Trapanal
Pharmacodynamics & Biochemistry
Thiopental (Pentothal, sodium thiopental) is an ultra-short-acting thiobarbiturate: the sulphur analogue of pentobarbital. Like other barbiturates it is a positive allosteric modulator of the GABA-A receptor, prolonging GABA-evoked chloride-channel opening and, at anaesthetic concentrations, opening the channel directly. It also blocks neuronal nicotinic acetylcholine receptors. The result is rapid, dose-dependent CNS depression with no ceiling: deep enough for surgical anaesthesia and, in overdose, for fatal respiratory and cardiovascular collapse. Its hallmark is its kinetics. Given intravenously it is so lipophilic that it reaches the brain and produces unconsciousness within about 30–45 seconds, but consciousness returns after only ≈5–10 minutes, not because the drug is eliminated, but because it redistributes out of the brain into muscle and fat. Its actual terminal elimination half-life is long (≈5.5–26 h) and it is metabolised in the liver (partly to pentobarbital), so repeated or continuous dosing accumulates and greatly prolongs recovery (a 'context-sensitive' effect). This rapid on/off single-dose profile made thiopental a classic intravenous induction agent. The same reliable, deep suppression underlies its use in barbiturate coma, its historical reputation as a 'truth serum', and its role as the first drug in lethal-injection protocols.
Biological targets
- GABA-A
Binding & functional measurements
Pharmacokinetics
| Bioavailability | IV (100%) |
| Tmax | Not reported |
| Half-life | Clinical ≈5–10 min (redistribution), terminal ≈5.5–26 h |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Hepatic (major metabolite pentobarbital) |
| Excretion | Renal (metabolites) |
Toxicology & Safety
Not reported
Thiopental produces profound respiratory and cardiovascular depression with no ceiling effect and a low therapeutic index, so it is given only by anaesthetists able to manage a lost airway and support the circulation. Even an induction dose causes apnoea and a fall in blood pressure. It is dangerous with any other CNS depressant. There is no specific antidote (flumazenil does not reverse barbiturates). Management is supportive. Extravasation or accidental intra-arterial injection can cause severe tissue damage. Repeated dosing accumulates, its clinical brevity is redistribution, not elimination, prolonging sedation. It is not a drug of casual misuse, but its reliable lethality is why it has been used for capital punishment and euthanasia.[2]
Legal Status
US: Schedule III. UK: Class B (Schedule 3). DE: Prescription only (Rx)
Interactions & Contraindications
Drug interactions
Contraindications
No interactions or contraindications listed.
Usage & Context
- An intravenous anaesthetic used to induce general anaesthesia (rapid 'off' after a single dose) and, by infusion, to produce a barbiturate coma for refractory status epilepticus and dangerously raised intracranial pressure.
- Historically promoted as a 'truth serum' for interrogation (its reliability for that is disputed), and used as the first agent in three-drug lethal-injection protocols and in euthanasia.
- Its manufacture has largely ceased in the West: the sole US maker (Hospira) stopped production in 2011 and the EU banned its export for use in executions, so it has become scarce.
Sources & Evidence
- PubChem: Thiopental (CID 3000715) — identifiers & experimental properties
- Wikipedia: Sodium thiopental — GABA-A mechanism, redistribution pharmacokinetics, anaesthetic/coma/lethal-injection uses, manufacturing cessation & legal status CC BY-SA 4.0
- DEA Diversion Control Division: Controlled Substance Schedules (thiopental is Schedule III)
- GOV.UK: Controlled drugs list — thiopental is Class B / Schedule 3 (Misuse of Drugs legislation) OGL v3.0