Thiobarbital

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Thiobarbital
Thiobarbital.svg
Identifiers
  • 5,5-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.929 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C8H12N2O2S
Molar mass 200.259 g·mol−1
3D model (JSmol)
  • O=C1NC(=S)NC(=O)C1(CC)CC
  • 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) Yes check.svgY
  • Key:QGVNJRROSLYGKF-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Thiobarbital is a drug which is a barbiturate derivative. It is the thiobarbiturate analogue of barbital.

Synthesis

Thiobarbital synthesis: Thiobarbital synthesis.svg
Thiobarbital synthesis:

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

Related Research Articles

Phosphorus Chemical element, symbol P and atomic number 15

Phosphorus is a chemical element with the symbol P and atomic number 15. Elemental phosphorus exists in two major forms, white phosphorus and red phosphorus, but because it is highly reactive, phosphorus is never found as a free element on Earth. It has a concentration in the Earth's crust of about one gram per kilogram. In minerals, phosphorus generally occurs as phosphate.

Phosphine Chemical compound hydrogen phosphide

Phosphine is a colorless, flammable, highly toxic compound with the chemical formula PH3, classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting fish, due to the presence of substituted phosphine and diphosphane. With traces of P2H4 present, PH3 is spontaneously flammable in air (pyrophoric), burning with a luminous flame. Phosphine is a highly toxic respiratory poison, and is immediately dangerous to life or health at 50 ppm. Phosphine has a trigonal pyramidal structure.

In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation.

Amobarbital Barbiturate

Amobarbital is a drug that is a barbiturate derivative. It has sedative-hypnotic properties. It is a white crystalline powder with no odor and a slightly bitter taste. It was first synthesized in Germany in 1923. It is considered a short to intermediate acting barbiturate. If amobarbital is taken for extended periods of time, physiological and psychological dependence can develop. Amobarbital withdrawal mimics delirium tremens and may be life-threatening. Amobarbital was manufactured by Eli Lilly and Company in the US under the brand name Amytal in bright blue bullet shaped capsules or pink tablets containing 50, 100, or 200 milligrams of the drug. The drug was also manufactured generically. Amobarbital was widely misused, known as "Blue Heavens" on the street. Amytal, as well as Tuinal, a combination drug containing equal quantities of secobarbital and amobarbital, were both manufactured by Eli Lilly until the late-1990s. However, as the popularity of benzodiazepines increased, prescriptions for these medications became increasingly rare beginning in the mid to late-1980s.

Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid itself is not pharmacologically active. The compound was first synthesised by Adolf von Baeyer.

Thioamide

A thioamide is a functional group with the general structure R–CS–NR′R″, where R, R′, and R″ are organic groups. They are analogous to amides but they exhibit greater multiple bond character along the C-N bond, resulting in a larger rotational barrier. One of the best-known thioamides is thioacetamide, which is used as a source of the sulfide ion and is a building block in heterocyclic chemistry.

Barbital Chemical compound

Barbital, marketed under the brand names Veronal for the pure acid and Medinal for the sodium salt, was the first commercially available barbiturate. It was used as a sleeping aid (hypnotic) from 1903 until the mid-1950s. The chemical names for barbital are diethylmalonyl urea or diethylbarbituric acid; hence, the sodium salt is known also as sodium diethylbarbiturate.

Phosphorus pentasulfide Chemical compound

Phosphorus pentasulfide is the inorganic compound with the formula P2S5 or dimer P4S10. This yellow solid is the one of two phosphorus sulfides of commercial value. Samples often appear greenish-gray due to impurities. It is soluble in carbon disulfide but reacts with many other solvents such as alcohols, DMSO, and DMF.

Joseph von Mering German physician

Josef, Baron von Mering was a German physician.

Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.

Hexobarbital Chemical compound

Hexobarbital or hexobarbitone, sold both in acid and sodium salt forms as Citopan, Evipan, and Tobinal, is a barbiturate derivative having hypnotic and sedative effects. It was used in the 1940s and 1950s as an agent for inducing anesthesia for surgery, as well as a rapid-acting, short-lasting hypnotic for general use, and has a relatively fast onset of effects and short duration of action. It was also used to murder women prisoners at Ravensbrück concentration camp. Modern barbiturates have largely supplanted the use of hexobarbital as an anesthetic, as they allow for better control of the depth of anesthesia. Hexobarbital is still used in some scientific research.

Molecular solid Solid consisting of discrete molecules

A molecular solid is a solid consisting of discrete molecules. The cohesive forces that bind the molecules together are van der Waals forces, dipole-dipole interactions, quadrupole interactions, π-π interactions, hydrogen bonding, halogen bonding, London dispersion forces, and in some molecular solids, coulombic interactions. Van der Waals, dipole interactions, quadrupole interactions, π-π interactions, hydrogen bonding, and halogen bonding are typically much weaker than the forces holding together other solids: metallic, ionic, and network solids. Intermolecular interactions, typically do not involve delocalized electrons, unlike metallic and certain covalent bonds. Exceptions are charge-transfer complexes such as the tetrathiafulvane-tetracyanoquinodimethane (TTF-TCNQ), a radical ion salt. These differences in the strength of force and electronic characteristics from other types of solids give rise to the unique mechanical, electronic, and thermal properties of molecular solids.

Allotropes of phosphorus Solid forms of the element phosphorus

Elemental phosphorus can exist in several allotropes, the most common of which are white and red solids. Solid violet and black allotropes are also known. Gaseous phosphorus exists as diphosphorus and atomic phosphorus.

Barbiturate Class of sedative medication derived from barbituric acid

A barbiturate is a drug that acts as a central nervous system depressant. Barbiturates are effective as anxiolytics, hypnotics, and anticonvulsants, but have physical and psychological addiction potential as well as overdose potential among other possible adverse effects. They have largely been replaced by benzodiazepines and nonbenzodiazepines ("Z-drugs") in routine medical practice, particularly in the treatment of anxiety and insomnia, due to the significantly lower risk of addiction and overdose and the lack of an antidote for barbiturate overdose. Despite this, barbiturates are still in use for various purposes: in general anesthesia, epilepsy, treatment of acute migraines or cluster headaches, acute tension headaches, euthanasia, capital punishment, and assisted suicide.

Barbiturate dependence develops with regular use of barbiturates. This in turn may lead to a need for increasing doses of the drug to get the original desired pharmacological or therapeutic effect. Barbiturate use can lead to both addiction and physical dependence, and as such they have a high potential for excess or non-medical use, however, it does not affect all users. Management of barbiturate dependence involves considering the affected person's age, comorbidity and the pharmacological pathways of barbiturates.

Akira Ogata was a Japanese chemist and the first to synthesize methamphetamine in crystalline form in 1919.

The Dille–Koppanyi reagent is used as a simple spot-test to presumptively identify barbiturates. It is composed of a mixture of two solutions. Part A is 0.1 g of cobalt(II) acetate dihydrate dissolved in 100 ml of methanol mixed with 0.2 ml of glacial acetic acid. Part B made up of is 5% isopropylamine (v/v) in methanol. Two drops of A are dropped onto the substance followed by one drop of B and any change in colour is observed.

Amphetamine and methamphetamine are central nervous system stimulants used to treat a variety of conditions. When used recreationally, they are colloquially known as "speed." Amphetamine was first synthesized in 1887 in Germany by Romanian chemist Lazăr Edeleanu, who named it phenylisopropylamine. Around the same time, Japanese organic chemist Nagai Nagayoshi isolated ephedrine from the Chinese ephedra plant and later developed a method for ephedrine synthesis. Methamphetamine was synthesized from ephedrine in 1893 by Nagayoshi. Neither drug had a pharmacological use until 1934, when Smith, Kline & French began selling amphetamine as an inhaler under the trade name Benzedrine for congestion.

3-HO-PCP Chemical compound

3-Hydroxyphencyclidine (3-HO-PCP) is a dissociative of the arylcyclohexylamine class related to phencyclidine (PCP) that has been sold online as a designer drug.

IPTBO Chemical compound

IPTBO is a bicyclic phosphate convulsant. It is an extremely potent GABA receptor antagonist that can cause violent convulsions in mice.

References

  1. Fischer E, Dilthey A (1904). "Ueber C-Dialkylbarbitursäuren und über die Ureïde der Dialkylessigsäuren". Justus Liebig's Annalen der Chemie. 335 (3): 334–368. doi:10.1002/jlac.19043350303.
  2. Carrington HC (1944). "45. The action of phosphorus pentasulphide on barbituric acids". Journal of the Chemical Society (Resumed): 124. doi:10.1039/JR9440000124.