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Racemic mixture

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In chemistry, a racemic mixture or racemate () is a mixture that has equal amounts (50:50) of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. HistoryThe first known racemic mixture was racemic acid, which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid.

Tartaric acidTartaric acidTartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes but also in tamarinds, bananas, avocados, and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. Potassium bitartrate is commonly mixed with sodium bicarbonate and is sold as baking powder used as a leavening agent in food preparation.Racemic acidRacemic acidRacemic acid is an old name for an optically inactive or racemic form of tartaric acid. It is an equal mixture of two mirror-image isomers (enantiomers), optically active in opposing directions. Racemic acid does not occur naturally in grape juice, although L-tartaric acid does.EnantiomerEnantiomerIn chemistry, an enantiomer (/ɪˈnænti.əmər, ɛ-, -oʊ-/ ih-NAN-tee-ə-mər), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities which are mirror images of each other and non-superposable. Enantiomer molecules are like right and left hands: one cannot be superposed onto the other without first being converted to its mirror image.Chirality (chemistry)Chirality (chemistry)In chemistry, a molecule or ion is called chiral () if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality (). The terms are derived from Ancient Greek χείρ (cheir) 'hand'; which is the canonical example of an object with this property.IsomerIsomerIn chemistry, isomers are molecules or polyatomic ions with an identical molecular formula – that is, the same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism refers to the existence or possibility of isomers. Isomers do not necessarily share similar chemical or physical properties.Louis PasteurLouis PasteurLouis Pasteur (; French: [lwi pastœʁ] ; 27 December 1822 – 28 September 1895) was a French chemist, pharmacist, and microbiologist renowned for his discoveries of the principles of vaccination, microbial fermentation, and pasteurization, the last of which was named after him.MethamphetamineMethamphetamineCentral nervous system stimulantPharmaceutical compoundBall-and-stick models of methamphetamine enantiomersClinical dataPronunciation(), (), () Trade namesDesoxyn, othersOther namesN-methylamphetamine, N,α-dimethylphenethylamine, desoxyephedrineAHFS/Drugs.comMonographPregnancycategoryAU: X (High risk)The system is developed for medicine that can be prescribed, but the equivalent is category X.DependenceliabilityPhysical: NonePsychological: Very highAddictionliabilityVery highRoutes ofadministrationBy mouth, intravenous, intramuscular, subcutaneous, inhalation, insufflation, rectal, vaginalDrug classStimulant;Serotonin–norepinephrine–dopamine releasing agentATC codeN06BA03 (WHO) Legal statusLegal statusAU: S8 (Controlled drug)BR: Class F2 (Prohibited psychotropics)CA: Schedule IDE: Anlage II (Authorized trade only, not prescriptible)NZ: Class AUK: Class AUS: Schedule IIUN: Psychotropic Schedule IIEU: Rx-onlySE: Förteckning IPharmacokinetic dataBioavailabilityOral: 67%Intranasal: 79%Inhalation: 67–90%Intravenous: 100%Protein bindingVaries widelyMetabolismCYP2D6 and FMO3Metabolites• Amphetamine • Pholedrine • N-Hydroxymethamphetamine • NorephedrineOnset of actionOral: 3 hours (peak)Intranasal: <15 minutesInhalation: <18 minutesIntravenous: <15 minutesElimination half-life9–12 hours (range 5–30 hours); irrespective of routeDuration of action8–12 hoursExcretionPrimarily kidneyIdentifiersIUPAC name(RS)-N-methyl-1-phenylpropan-2-amineCAS Number537-46-2(dl)-Methamphetamine hydrochloride: 300-42-5PubChemCID1206IUPHAR/BPS4803DrugBankDB01577ChemSpider1169UNII44RAL3456C(dl)-Methamphetamine hydrochloride: 24GNZ56D62KEGGD08187ChEBICHEBI:6809ChEMBLChEMBL1201201PDB ligandB40 (PDBe, RCSB PDB)CompTox Dashboard(EPA)DTXSID3043861ECHA InfoCard100.028.690 100.023.121, 100.028.690Chemical and physical dataFormulaC10H15NMolar mass149.237 g·mol3D model (JSmol)Interactive imageChiralityRacemic mixtureMelting point170 °C (338 °F) Boiling point212 °C (414 °F) at 760 mmHgSMILESCNC(C)Cc1ccccc1InChIInChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3Key:MYWUZJCMWCOHBA-UHFFFAOYSA-N (verify)Methamphetamine is a central nervous system (CNS) stimulant that is primarily used as a recreational or performance-enhancing drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder (ADHD).ThalidomideThalidomideThalidomide, sold under the brand names Contergan, Distaval and Thalomid among others, is an oral administered medication used to treat a number of cancers (e.g., multiple myeloma), graft-versus-host disease, and skin disorders (e.g., complications of leprosy such as skin lesions).Amount of substanceAmount of substanceIn chemistry, the amount of substance (symbol n) in a given sample of matter is defined as a ratio (n = N/NA) between the number of elementary entities (N) and the Avogadro constant (NA). It is one of the seven base quantities of the International System of Units, SI. The unit of amount of substance in the SI is the mole (symbol: mol), a base unit.Carl LinnaeusCarl LinnaeusSwedish biologist and physician (1707–1778)Carl Linnaeus (23 May 1707 – 10 January 1778), also known after ennoblement in 1761 as Carl von Linné, was a Swedish biologist and physician who formalised binomial nomenclature, the modern system of naming organisms. He is known as the "father of modern taxonomy". Many of his writings were in Latin; his name is rendered in Latin as Carolus Linnæus and, after his 1761 ennoblement, as Carolus a Linné.ChemistryChemistryChemistry is the scientific study of the properties and behavior of matter. It is a physical science within the natural sciences that studies matter: composition, structure, properties, behavior and the changes they undergo during reactions with other substances. Chemistry also addresses the nature of chemical bonds in chemical compounds. In the scope of its subject, chemistry occupies an intermediate position between physics and biology.StereospecificityIn chemistry, stereospecificity is the property of a reaction mechanism that leads to different stereoisomeric reaction products from different stereoisomeric reactants, or which operates on only one (or a subset) of the stereoisomers.

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