Sodium thiopental
Systematic (IUPAC) name
sodium 5-ethyl-5-(2-methylpentyl)-4,6-dioxo- -1,4,5,6-tetrahydropyrimidine-2-thiolate
Identifiers
CAS number	76-75-5
ATC code	N01AF03 N05CA19
PubChem	3000714
DrugBank	APRD00660
Chemical data
Formula	C11H17N2NaO2S
Mol. mass	264.321 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	5.89[1]-26 hours[2]
Excretion	?
Therapeutic considerations
Pregnancy cat.	? from http://www. ... Image File history File links Tiopental. ... Image File history File links Size of this preview: 450 × 599 pixelsFull resolution (826 × 1100 pixel, file size: 212 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... For sodium in the diet, see Edible salt. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Standard atomic weight 32. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...
Legal status	Schedule III(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...
Routes	Oral, intravenous

Sodium thiopental, better known as Sodium Pentothal (a trademark of Abbott Laboratories), thiopental, thiopentone sodium, or trapanal, is a rapid-onset short-acting barbiturate general anaesthetic. Sodium thiopental is a depressant and is sometimes used during interrogations not to cause pain (in fact it may have just the opposite effect) but to weaken the resolve of the subject and make him or her more compliant to pressure. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... “(TM)” redirects here. ... Abbott Laboratories (NYSE: ABT) is a diversified pharmaceuticals and health care company. ... Barbituric acid, the basic structure of all barbiturates Barbiturates are drugs that act as central nervous system depressants, and by virtue of this they produce a wide spectrum of effects, from mild sedation to anesthesia. ... A general anaesthetic drug is an anaesthetic (or anesthetic AE) drug that brings about a reversible loss of consciousness. ...

Barbiturates

Main article: Barbiturate

Barbiturates are a class of drugs that act on the GABA_A receptor in the brain and spinal cord. The GABA_A receptor is an inhibitory channel which decreases neuronal activity and the barbiturates enhance the inhibitory action of the GABA_A receptor. Barbiturates, benzodiazepines, and alcohol all bind to the GABA_A receptor, yet the barbiturates bind with the highest affinity with longer receptor binding half-lives. This explains why overdoses of barbiturates may be lethal whereas overdoses of benzodiazepines alone are typically not lethal. Another explanation is that barbiturates can activate GABA receptors in the absence of the GABA molecule, whereas benzodiazepines require GABA to be present to have an effect: this may explain the more widespread effects of barbiturates in the central nervous system. Barbiturates have anesthetic, sedative, and hypnotic properties. Barbiturates do not have analgesic effects.^[3] Barbituric acid, the basic structure of all barbiturates Barbiturates are drugs that act as central nervous system depressants, and by virtue of this they produce a wide spectrum of effects, from mild sedation to anesthesia. ... The GABAA receptor is one of the three ligand-gated ion channels responsible for mediating the effects of Gamma-AminoButyric Acid (GABA), the major inhibitory neurotransmitter in the brain. ... Alprazolam 2mg tablets The benzodiazepines (pronounced , or benzos for short) are a class of psychoactive drugs considered as minor tranquilizers with varying hypnotic, sedative, anxiolytic, anticonvulsant, muscle relaxant and amnesic properties, which are brought on by slowing down the central nervous system. ... A sedative is a substance that depresses the central nervous system (CNS), resulting in calmness, relaxation, reduction of anxiety, sleepiness, and slowed breathing, as well as slurred speech, staggering gait, poor judgment, and slow, uncertain reflexes. ... Hypnotic drugs are a class of drugs that induce sleep, used in the treatment of severe insomnia. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ...

Uses

Anesthesia

Thiopental is an ultra-short acting barbiturate and is most commonly used in the induction phase of general anesthesia. Following intravenous injection the drug rapidly reaches the brain and causes unconsciousness within 30–45 seconds. At one minute, the drug attains a peak concentration of about 60% of the total dose in the brain. Thereafter, the drug distributes to the rest of the body and in about 5–10 minutes the concentration is low enough in the brain such that consciousness returns. In modern medical practice, general anaesthesia (AmE: anesthesia) is a state of total unconsciousness resulting from general anaesthetic drugs. ... Intravenous therapy or IV therapy is the giving of liquid substances directly into a vein. ... An injection is a method of putting liquid into the body with a hollow needle and a syringe which is pierced through the skin long enough for the material to be forced into the body. ...

Thiopental is not used for the maintenance of anesthesia in surgical procedures because, in infusion, it displays zero-order elimination kinetics, leading to a prolonged period before consciousness is regained. Instead, anesthesia is usually maintained with an inhaled anesthetic agent. This class of drugs has a relatively rapid elimination, so that stopping the inhaled anesthetic will allow rapid return of consciousness. Thiopental would have to be given in large amounts to maintain an anesthetic plane, and because of its 11.5–26 hour half-life, consciousness would take a long time to return.^[4] It has been suggested that Effective half-life be merged into this article or section. ... Inhalational anaesthetics are gases or vapours possessing anaesthetic qualities. ...

In veterinary medicine, thiopental is also used for the induction of anesthesia. Since thiopental is redistributed to fat, certain breeds of dogs, primarily the sight hounds can have prolonged recoveries from thiopental due to their lack of body fat and lean body mass. Thiopental is always administered intravenously as it can be fairly irritating; severe tissue necrosis and sloughing can occur if the drug is injected incorrectly into the tissue surrounding the vein rather than into the bloodstream. Veterinary medicine is the application of medical, diagnostic, and therapeutic principles to companion, domestic, exotic, wildlife, and production animals. ... Veterinary anesthesia is anesthesia performed on animals (excluding humans) performed by a veterinarian. ... The Whippet shows the characteristic long legs, deep chest, and narrow waist of a sight hound. ...

Medically induced coma

In addition to anesthesia induction, thiopental can be used to induce medical comas. Even though the drug is described as an ultra-short acting barbiturate, the drug's half-life is much longer and giving a larger dose ensures adequate concentrations in the brain to maintain anesthesia. Patients with brain swelling, causing elevation of the intracranial pressure, either secondary to trauma or following surgery may benefit from this drug. Thiopental, and the barbiturate class of drugs, decrease neuronal activity and therefore decrease the production of osmotically active metabolites which in turn decrease swelling. Patients with significant swelling have improved outcomes following the induction of coma. Reportedly, thiopental has been shown to be superior to pentobarbital^[5] in reducing intracranial pressure. Pentobarbital is a short acting barbiturate that is available as both a free acid and a sodium salt, the former of which is only slightly soluble in water and ethanol. ...

Euthanasia

Thiopental is used intravenously for the purposes of euthanasia. The Belgians and the Dutch have created a protocol that recommends sodium thiopental as the ideal agent to induce coma followed by pancuronium bromide.^[6] For mercy killings not performed on humans, see animal euthanasia. ... Pancuronium bromide is a chemical compound, used in medicine with the brand name Pavulon® (Organon Pharmaceuticals). ...

Intravenous administration is the most reliable and rapid way to accomplish euthanasia and therefore can be safely recommended. A coma is first induced by intravenous administration of 20 mg/kg thiopental sodium (Nesdonal) in a small volume (10 ml physiological saline). Then a triple intravenous dose of a non-depolarizing neuromuscular muscle relaxant is given, such as 20 mg pancuronium dibromide (Pavulon) or 20 mg vecuronium bromide (Norcuron). The muscle relaxant should preferably be given intravenously, in order to ensure optimal availability. Only for pancuronium dibromide (Pavulon) are there substantial indications that the agent may also be given intramuscularly in a dosage of 40 mg.[1]

Vecuronium bromide (trade name Norcuron) is a muscle relaxant in the category of non depolarising neuromuscular blocking agents. ... Pancuronium bromide is a chemical compound, used in medicine with the brand name Pavulon® (Organon International). ...

Lethal injection

Along with pancuronium bromide and potassium chloride, thiopental is used in 37 states of the U.S. to execute prisoners by lethal injection. A megadose is given which places the subject into a rapidly induced coma. Executions using the three drug combination are usually effective in approximately 10 minutes, but have been known to take several times this length. The use of thiopental alone is hypothesized to cause death in approximately 45 minutes.^[7] Pancuronium bromide is a chemical compound, used in medicine with the brand name Pavulon® (Organon Pharmaceuticals). ... The chemical compound potassium chloride (KCl) is a metal halide composed of potassium and chlorine. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from... This article is about the execution and euthanasia method. ...

Truth serum

Thiopental is still used in some places as a truth serum.^[8] The barbiturate drugs as a class decrease higher cortical brain functioning. Psychiatrists hypothesize that because lying is more complex than telling the truth, suppression of the higher cortical functions may lead to the uncovering of the "truth." However, the reliability of confessions made under thiopental is dubious; the drug tends to make subjects chatty and cooperative with interrogators, but a practiced liar or someone who has a false story firmly established would still be quite able to lie while under the influence of the drug.^{[citation needed]} // A truth drug (or truth serum) is a drug used for the purposes of obtaining accurate information from an unwilling subject, most often by a police, intelligence, or military organization on a prisoner. ...

Psychiatry

Psychiatrists have used thiopental to desensitize patients with phobias,[2] and to "facilitate the recall of painful, repressed memories."[3] One psychiatrist who worked with thiopental is Professor Jan Bastiaans, who used this procedure to help release trauma in victims of the Nazis.[4]

Metabolism

As with all lipid soluble anaesthetic drugs, the short duration of action of STP is almost entirely due to its redistribution away from central circulation towards muscle and fat tissue. Once redistributed the free fraction in the blood is metabolised in the liver. Sodium thiopental is mainly metabolized to pentobarbital,^[9] 5-ethyl-5-(1'-methyl-3'-hydroxybutyl)-2-thiobarbituric acid, and 5-ethyl-5-(1'-methyl-3'-carboxypropyl)-2-thiobarbituric acid.^[10] Pentobarbital is a short acting barbiturate that is available as both a free acid and a sodium salt, the former of which is only slightly soluble in water and ethanol. ...

Dosage

The usual dose range for induction of anesthesia using thiopentone is from 3 to 7 mg/kg; however, there are many factors that can alter this. Premedication with sedatives such as benzodiazepines or clonidine will reduce requirements, as do specific disease states and other patient factors. Benzodiazepine tablets The benzodiazepines are a class of drugs with hypnotic, anxiolytic, anticonvulsant, amnestic and muscle relaxant properties. ... Clonidine is a direct-acting adrenergic agonist prescribed historically as an anti-hypertensive agent. ...

Side effects

As with nearly all anesthetic drugs, thiopental causes cardiovascular and respiratory depression resulting in hypotension, apnea and airway obstruction. For these reasons, only suitably trained medical personnel should give thiopental in an environment suitably equipped to deal with these effects. Side effects include headache, emergence delirium, prolonged somnolence and nausea. The hangover effects may last up to 36 hours. Anesthesia or anaesthesia (see spelling differences) has traditionally meant the condition of having the perception of pain and other sensations blocked. ... This article does not cite any references or sources. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... Apnea (British spelling - apnoea) (Greek απνοια, from α-, privative, πνεειν, to breathe) is a technical term for suspension of external breathing. ... The airways are those parts of the respiratory system through which air flows, to get from the external environment to the alveoli. ... This article is about the mental state and medical condition. ... Somnolence (or drowsiness) is a state of near-sleep, a strong desire for sleep, or sleeping for unusually long periods. ... For other uses, see Nausea (disambiguation). ...

Drug interaction

Co-administration of pentoxifylline and thiopental causes death by acute pulmonary oedema in rats. This pulmonary oedema was not mediated by cardiac failure or by pulmonary hypertension but was due to increased pulmonary vascular permeability.^[11] Pentoxifylline is the International Nonproprietary Name(INN) of a drug sold by Aventis under the name Trental. ... Congestive heart failure (CHF) (also called heart failure) is the inability of the heart to pump blood effectively to the body, or requiring elevated filling pressures in order to pump effectively. ... In medicine, pulmonary hypertension (PH) is an increase in blood pressure in the pulmonary artery or lung vasculature, leading to shortness of breath, dizziness, fainting, and other symptoms, all of which are exacerbated by exertion. ...

History

Sodium thiopental was discovered in the early 1930s by Ernest H. Volwiler and Donalee L. Tabern, working for Abbott Laboratories. It was first used in human beings on March 8, 1934, by Dr. Ralph M. Waters^[12] in an investigation of its properties, which were short-term anesthesia and surprisingly little analgesia.^[13] Three months later,^[14] Dr. John S. Lundy started a clinical trial of thiopental at the Mayo Clinic at the request of Abbott.^[15] Ernest H. Volwiler (August 22, 1893-1992) spent his entire career at Abbott Laboratories working his way from staff chemist to CEO. A Hamilton, Ohio native, Volwiler received a bachelors degree from Miami University in Oxford, Ohio and a Masters degree and Ph. ... Abbott Laboratories (NYSE: ABT) is a diversified pharmaceuticals and health care company. ... Main campus in downtown Rochester, Minnesota. ...

It is famously associated with a number of anesthetic deaths in victims of the attack on Pearl Harbor. These deaths, relatively soon after its discovery, were due to excessive doses given to shocked trauma patients. Evidence has however become available through freedom of information legislation and has been reviewed in the "British Journal of Anaesthesia".^[16] Thiopentone anaesthesia was in its early days, but nevertheless only 13 of 344 wounded admitted to the Tripler Army Hospital did not survive. This article is about the harbor in Hawaii. ...

Thiopental is still rarely encountered as a recreational drug, usually stolen from veterinarians or other legitimate users of the drug, however more common sedatives such as benzodiazepines are usually preferred, and abuse of thiopental tends to be uncommon and opportunistic. Recreational drug use is the use of psychoactive drugs for recreational rather than medical or spiritual purposes, although the distinction is not always clear. ... Benzodiazepine tablets The benzodiazepines are a class of drugs with hypnotic, anxiolytic, anticonvulsant, amnestic and muscle relaxant properties. ...

References

Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st Century. ... is the 217th day of the year (218th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st Century. ... is the 217th day of the year (218th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st Century. ... is the 217th day of the year (218th in leap years) in the Gregorian calendar. ...

External links

• PubChem Substance Summary: Thiopental
• Pentothal Abbott Laboratories. 1993.