Names | |
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Preferred IUPAC name 2-Acetamidoethane-1-sulfonic acid | |
Other names NAcT | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C4H9NO4S | |
Molar mass | 167.18 g·mol−1 |
Appearance | Solid |
Soluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
N-Acetyltaurine (NAcT) is an endogenous metabolite. Biochemically, N-acetyltaurine is formed as a result of an acetylation of taurine. The main substrate for this reaction is acetate. [1] An increase of endogenous N-acetyltaurine concentrations was observed after the consumption of alcohol and after extended physical activity (ketoacidosis). [2] [3] [4]
N-Acetyltaurine was first mentioned in 1990 as a compound in the droplets of the orb spider's viscid spiral. [5] Based on its high hygroscopicity, N-acetyltaurine is an important ingredient which ensures the spider web's flexibility.
As a biomarker for ethanol metabolism, N-acetyltaurine was first mentioned in a mice study in 2012. [1] Another study in 2015 focused on the effect of endurance training on an increase in N-acetyltaurine concentrations. [2] The first study focusing on the forensic context of alcohol biomarker analysis in human urine was published in 2016. [4] One year later, in 2017 an evaluation of N-acetyltaurine as an alcoholmarker in human blood followed. [3]
N-Acetyltaurine is a direct alcohol biomarker which represents the oxidative pathway of ethanol metabolism. Other direct alcohol biomarkers such as fatty acid ethyl esters (FAEE), ethyl glucuronide, ethyl sulfate, and phosphatidylethanol reflect the non-oxidative pathway of alcohol metabolism, based on conjunction reactions (biotransformation).
The fact that N-acetyltaurine is an endogenous metabolite reduces its significane as an alcohol biomarker: A distinction between endogenous N-acetyltaurine concentrations and alcohol induced concentrations is necessary.
During a drinking study with a target blood alcohol concentrations of 0.8 g/kg, an alcohol induced concentration of N-acetyltaurine which was about ten folds higher than the endogenous concentration was observed. [4] In blood the alcohol induced increase was only twofold. [3] Based on these observations, it was concluded that N-acetyltaurine is excreted very efficiently by the kidney.
N-Acetyltaurine can be quantified by a combination of high performance liquid chromatography and mass spectrometry (MS/MS). Due to the high hydrophilicity of N-acetyltaurine, the hydrophilic interaction chromatography (HILIC) is the method of choice in order to separate the analyte from the matrix components. [3] [4]
Blood alcohol content (BAC), also called blood alcohol concentration or blood alcohol level, is a measurement of alcohol intoxication used for legal or medical purposes. For example, a BAC of 0.10 means that there is 0.10 g of alcohol for every 100 ml of blood, which is the same as 21.7 mmol/l. A BAC of 0.0 is sober, while in the United States 0.08 is legally intoxicated for purposes of driving for those above 21, and above that is very impaired. BAC levels above 0.40 are potentially fatal.
Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic chemical compound. It is a simple alcohol with the chemical formula C2H6O. Its formula can be also written as CH
3−CH
2−OH or C
2H
5OH (an ethyl group linked to a hydroxyl group), and is often abbreviated as EtOH. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive drug, recreational drug, and the active ingredient in alcoholic drinks.
Drug metabolism is the metabolic breakdown of drugs by living organisms, usually through specialized enzymatic systems. More generally, xenobiotic metabolism is the set of metabolic pathways that modify the chemical structure of xenobiotics, which are compounds foreign to an organism's normal biochemistry, such as any drug or poison. These pathways are a form of biotransformation present in all major groups of organisms and are considered to be of ancient origin. These reactions often act to detoxify poisonous compounds. The study of drug metabolism is called pharmacokinetics.
Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. It is a colorless oil although degraded samples can appear yellow.
Cocaethylene (ethylbenzoylecgonine) is the ethyl ester of benzoylecgonine. It is structurally similar to cocaine, which is the methyl ester of benzoylecgonine. Cocaethylene is formed by the liver when cocaine and ethanol coexist in the blood. In 1885, cocaethylene was first synthesized, and in 1979, cocaethylene's side effects were discovered.
Glucuronic acid is a uronic acid that was first isolated from urine. It is found in many gums such as gum arabic, xanthan, and kombucha tea and is important for the metabolism of microorganisms, plants and animals.
Fomepizole, also known as 4-methylpyrazole, is a medication used to treat methanol and ethylene glycol poisoning. It may be used alone or together with hemodialysis. It is given by injection into a vein.
Ethylone, also known as 3,4-methylenedioxy-N-ethylcathinone, is a recreational designer drug classified as an entactogen, stimulant, and psychedelic of the phenethylamine, amphetamine, and cathinone chemical classes. It is the β-keto analogue of MDEA ("Eve"). Ethylone has only a short history of human use and is reported to be less potent than its relative methylone. In the United States, it began to be found in cathinone products in late 2011.
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.
11-Hydroxy-Δ9-tetrahydrocannabinol, usually referred to as 11-hydroxy-THC, is the main active metabolite of tetrahydrocannabinol (THC), which is formed in the body after decarboxylated cannabis is consumed.
A hangover is the experience of various unpleasant physiological and psychological effects usually following the consumption of alcohol, such as wine, beer, and distilled spirits. Hangovers can last for several hours or for more than 24 hours. Typical symptoms of a hangover may include headache, drowsiness, concentration problems, dry mouth, dizziness, fatigue, gastrointestinal distress, absence of hunger, light sensitivity, depression, sweating, nausea, hyper-excitability, irritability, and anxiety.
Fatty acid esters (FAEs) are a type of ester that result from the combination of a fatty acid with an alcohol. When the alcohol component is glycerol, the fatty acid esters produced can be monoglycerides, diglycerides, or triglycerides. Dietary fats are chemically triglycerides.
Taurolidine is an antimicrobial that is used to try to prevent infections in catheters. Side effects and the induction of bacterial resistance is uncommon. It is also being studied as a treatment for cancer.
Ethyl glucuronide (EtG) is a metabolite of ethanol which is formed in the body by glucuronidation following exposure to ethanol, usually from drinking alcoholic beverages. It is used as a biomarker to test for ethanol use and to monitor alcohol abstinence in situations where drinking is prohibited, such as by the military, in alcohol treatment programs, in professional monitoring programs, in schools, liver transplant clinics, or in recovering alcoholic patients. In addition to its use to monitor abstinence and detect drinking, EtG also has potential for monitoring the amount of alcohol use over time because it can be detected in hair and nails, though the effectiveness of this has not yet been proven.
Phosphatidylethanols (PEth) are a group of phospholipids formed only in the presence of ethanol via the action of phospholipase D (PLD). The lipid accumulates in the brain and competes at agonists sites of lipid-gated ion channels contributing to alcohol intoxication. The chemical similarity of PEth to phosphatidic acid (PA) and phosphatidylinositol 4,5-bisphosphate (PIP2) suggest a likely broad perturbation to lipid signaling; the exact role of PEth as a competitive lipid ligand has not been studied extensively.
Breath gas analysis is a method for gaining information on the clinical state of an individual by monitoring volatile organic compounds (VOCs) present in the exhaled breath. Exhaled breath is naturally produced by the human body through expiration and therefore can be collected in non-invasively and in an unlimited way. VOCs in exhaled breath can represent biomarkers for certain pathologies. Breath gas concentration can then be related to blood concentrations via mathematical modeling as for example in blood alcohol testing. There are various techniques that can be employed to collect and analyze exhaled breath. Research on exhaled breath started many years ago, there is currently limited clinical application of it for disease diagnosis. However, this might change in the near future as currently large implementation studies are starting globally.
5-MAPB is an entactogenic designer drug similar to MDMA in its structure and effects.
Auto-brewery syndrome(ABS) is a condition characterized by the fermentation of ingested carbohydrates in the gastrointestinal tract of the body caused by bacteria or fungi. ABS is a rare medical condition in which intoxicating quantities of ethanol are produced through endogenous fermentation within the digestive system. The organisms responsible for ABS include various yeasts and bacteria, including Saccharomyces cerevisiae, S. boulardii, Candida albicans, C. tropicalis, C. krusei, C. glabrata, C. kefyr, C. parapsilosis, Klebsiella pneumoniae, and Enterococcus faecium. These organisms use lactic acid fermentation or mixed acid fermentation pathways to produce an ethanol end product. The ethanol generated from these pathways is absorbed in the small intestine, causing an increase in blood alcohol concentrations that produce the effects of intoxication without the consumption of alcohol.
Alcohol, sometimes referred to by the chemical name ethanol, is a psychoactive drug that is the active ingredient in drinks such as beer, wine, and distilled spirits. It is one of the oldest and most common recreational substances, causing the characteristic effects of alcohol intoxication ("drunkenness"). Among other effects, alcohol produces happiness and euphoria, decreased anxiety, increased sociability, sedation, impairment of cognitive, memory, motor, and sensory function, and generalized depression of central nervous system function. Ethanol is only one of several types of alcohol, but it is the only type of alcohol that is found in alcoholic beverages or commonly used for recreational purposes; other alcohols such as methanol and isopropyl alcohol are significantly more toxic. A mild, brief exposure to isopropanol, being only moderately more toxic than ethanol, is unlikely to cause any serious harm. Methanol, being profoundly more toxic than ethanol, is lethal in quantities as small as 10–15 milliliters.
4-EA-NBOMe is a substituted amphetamine and 25-NB derivative which has been sold as a designer drug. It was first identified by a forensic laboratory in Germany in 2014, but while its analytical properties and metabolism have been studied, its pharmacology remains unknown.
Luginbühl M, Rutjens S, König S, Furrer J, Weinmann W (October 2016). "N-Acetyltaurine as a novel urinary ethanol marker in a drinking study" (PDF). Analytical and Bioanalytical Chemistry. 408 (26): 7529–36. doi:10.1007/s00216-016-9855-7. PMID 27520321. S2CID 22179087.