In organic chemistry, the Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is oxidized to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine. It is one of the many oxidation reactions commonly referred to as 'activated DMSO' oxidations. The reaction is known for its mild character and wide tolerance of functional groups.
Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH3)2SO. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO is metabolised to compounds that leave a garlic-like taste in the mouth after DMSO is absorbed by skin.
Dimethyl ether (DME; also known as methoxymethane) is the organic compound with the formula CH3OCH3, (sometimes ambiguously simplified to C2H6O as it is an isomer of ethanol). The simplest ether, it is a colorless gas that is a useful precursor to other organic compounds and an aerosol propellant that is currently being demonstrated for use in a variety of fuel applications.
Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula (CH3)2S. It is the simplest thioether and has a characteristic disagreeable odor. It is a flammable liquid that boils at 37 °C (99 °F). It is a component of the smell produced from cooking of certain vegetables, notably maize, cabbage, beetroot, and seafoods. It is also an indication of bacterial contamination in malt production and brewing. It is a breakdown product of dimethylsulfoniopropionate (DMSP), and is also produced by the bacterial metabolism of methanethiol.
The branched-chain α-ketoacid dehydrogenase complex is a multi-subunit complex of enzymes that is found on the mitochondrial inner membrane. This enzyme complex catalyzes the oxidative decarboxylation of branched, short-chain alpha-ketoacids. BCKDC is a member of the mitochondrial α-ketoacid dehydrogenase complex family, which also includes pyruvate dehydrogenase and alpha-ketoglutarate dehydrogenase, key enzymes that function in the Krebs cycle.
This is the list of extremely hazardous substances defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. The list can be found as an appendix to 40 CFR 355. Updates as of 2006 can be seen on the Federal Register, 71 FR 47121.
TOM, or methylthio-methyl-methoxyamphetamine, is a series of lesser-known psychedelic drugs and substituted amphetamines with the molecular formula C12H19NOS. 2-TOM and 5-TOM are the 2- and 5-methylthio analogs of 2,5-dimethoxy-4-methylamphetamine (DOM), respectively. They were first synthesized by Alexander Shulgin and described in his book PiHKAL. Very little is known about their dangers or toxicity.
TOET (methylthio-ethyl-methoxyamphetamines) is a pair of lesser-known psychedelic drugs and substituted amphetamines. 2-TOET and 5-TOET are the 2- and 5-methylthio analogs of DOET, respectively. They were first synthesized by Alexander Shulgin and written up in his book PiHKAL. Very little is known about their dangers or toxicity.
5-MeS-DMT (5-methylthio-N,N-dimethyltryptamine) is a lesser-known psychedelic drug. It is the 5-methylthio analog of dimethyltryptamine (DMT). 5-MeS-DMT was first synthesized by Alexander Shulgin. In his book TiHKAL, the minimum dosage is listed as 15-30 mg. The duration listed as very short, just like DMT. 5-MeS-DMT produces similar effects to DMT, but weaker. Shulgin describes his feelings while on a low dose of this drug as "pointlessly stoned", although at a higher dose of 20 mg he says it is "quite intense" and suggests that a higher dose still might have full activity.
Metitepine, also known as methiothepin, is a drug described as a "psychotropic agent" of the tricyclic group which was never marketed. It acts as a non-selective antagonist of serotonin, dopamine, and adrenergic receptors and has antipsychotic properties.
Dimethyl disulfide (DMDS) is an organic chemical compound with the molecular formula CH3SSCH3. It is a flammable liquid with an unpleasant, garlic-like odor. The compound is colorless although impure samples often appear yellowish.
Cyanophos is a cholinesterase inhibitor used as an insecticide and avicide; for example, against rice stem borers and house flies. It is part of the chemical class of organophosphorus compounds, and is a yellow to reddish-yellow transparent liquid.
Endothion is an organic compound used as an insecticide and acaricides. It is part of the chemical class of organophosphorus compounds. It is generally described as white crystals with a slight odor. It is used as an insecticide, but not sold in the United States or Canada.
Metribuzin is a herbicide used both pre- and post-emergence in crops including soy bean, potatoes, tomatoes and sugar cane.
BAY-29952 is a broad spectrum insecticide. It is listed as an extremely hazardous substance according to the U.S. Emergency Planning and Community Right-to-Know Act.
Methional is an organic compound with the formula CH3SCH2CH2CHO. It is a colorless liquid that is a degradation product of methionine. It is a notable flavor in potato-based snacks, namely potato chips, one of the most popular foods containing methional. Traces of the compound can also be found in black tea and green tea based products. Methional contains both aldehyde and thioether functional groups. It is readily soluble in alcohol solvents, including propylene glycol and dipropylene glycol.
Dimethandrolone buciclate, or dimethandrolone bucyclate, also known as 7α,11β-dimethyl-19-nortestosterone 17β-buciclate, is a synthetic anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time. It is an androgen ester – specifically, the C17β buciclate (4-butylcyclohexane-1-carboxylate) ester of dimethandrolone, (7α,11β-dimethyl-19-nortestosterone) – and acts as a prodrug of dimethandrolone in the body. Dimethandrolone buciclate is or was under investigation as a potential male contraceptive.
R-16661 is an extremely toxic organophosphate insecticide. With an oral LD50 of 0.1 mg/kg in mice and rats, R-16661 is about 10 times more toxic than aldicarb, the most toxic carbamate insecticide.
2-Hydroxy-4-(methylthio)butyric acid is an organic compound with the structural formula CH3SCH2CH2CH(OH)CO2H. It is a white solid. In terms of functional groups, the molecule is a α-hydroxy carboxylic acid and a thioether. The compound is structurally related to the amino acid methionine by replacement of the amine with a hydroxy group.
