Tropane Alkylation
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Tropane Alkylation
Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca) and Solanaceae (including mandrake, henbane, deadly nightshade, datura, potato, tomato). Structurally, tropane is cycloheptane with a nitrogen bridge between carbons 1 and 5 and an additional methyl group attached to the nitrogen. While carbons 1 and 5 are asymmetric carbons, tropane itself is optically inactive due to mirror symmetry. 8-Azabicyclo .2.1ctane (tropane without the ''N''-methyl group) is known as nortropane or nor-tropane. See also * Phenyltropane * Tropane alkaloid * Tropine Tropine is a derivative of tropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol. It is a poisonous white hygroscopic crystalline powder. It is a heterocyclic alcohol and an amine. Tropine is a central building bl . ...
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Nitrogen
Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. It is a common element in the universe, estimated at Abundance of the chemical elements, seventh in total abundance in the Milky Way and the Solar System. At standard temperature and pressure, two atoms of the element chemical bond, bond to form N2, a colourless and odourless diatomic molecule, diatomic gas. N2 forms about 78% of Atmosphere of Earth, Earth's atmosphere, making it the most abundant chemical species in air. Because of the volatility of nitrogen compounds, nitrogen is relatively rare in the solid parts of the Earth. It was first discovered and isolated by Scottish physician Daniel Rutherford in 1772 and independently by Carl Wilhelm Scheele and Henry Cavendish at about the same time. The name was suggested by French chemist ...
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Henbane
Henbane (''Hyoscyamus niger'', also black henbane and stinking nightshade) is a poisonous plant belonging to tribe Hyoscyameae of the nightshade family ''Solanaceae''. Henbane is native to Temperate climate, temperate Europe and Siberia, and naturalised in Great Britain and Ireland. Historical use The name ''henbane'' dates from AD 1265; "bane" meant 'thing that causes death'. Other etymologies of ''henbane'' derive from the Indo-European stem ''bhelena'' meaning "crazy plant" and with the Proto-Germanic element ''bil'' meaning "vision", "hallucination", "magical power", and "miraculous ability". Historically, henbane was used in combination with other plants, such as the Mandragora officinarum, mandrake, the deadly nightshade, and datura, as an anaesthetic potion, and for its psychoactive properties in "magic brews". These psychoactive properties include visual hallucinations and a sensation of flight.Schultes & Smith 1976, p. 22 It was originally used in continental Europe, As ...
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Tropane Alkaloid
Tropane alkaloids are a class of bicyclic .2.1alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural associations. Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants. Classification Anticholinergics Anticholinergic drugs and deliriants: * Atropine, racemic hyoscyamine, from the deadly nightshade (''Atropa belladonna'') * Hyoscyamine, the ''levo''-isomer of atropine, from henbane (''Hyoscyamus niger''), mandrake ('' Mandragora officinarum'') and the sorcerers' tree ('' Latua pubiflora''). * Scopolamine, from henbane and ''Datura'' species (Jimson weed) All three acetylcholine-inhibiting chemicals can also be found in the leaves, stems, and flowers in varyi ...
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Phenyltropane
Phenyltropanes (PTs) were originally developed to reduce cocaine addiction and dependency. In general these compounds act as inhibitors of the plasmalemmal monoamine reuptake transporters. This research has spanned beyond the last couple decades, and has picked up its pace in recent times, creating numerous phenyltropanes as research into cocaine analogues garners interest to treat addiction. Uses Addiction The phenyltropane compounds were initially discovered by R. Clarke et al. during research to try and dissociate the stimulant properties of cocaine from its abuse and dependence liability. The first simple phenyltropanes to be made (WIN 35065-2 and WIN 34,428) were shown to be active in behavioral assays only for the ββ-isomers. The activity of the corresponding αβ-isomers was disappointing. It was later shown that WIN 35065-2 and WIN 34,428 are mostly dopamine selective reuptake inhibitors with some residual actions at the norepinephrine transporter (NET) and seroton ...
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Asymmetric Carbon
In stereochemistry, an asymmetric carbon is a carbon atom that is bonded to four different types of atoms or groups of atoms. The four atoms and/or groups attached to the carbon atom can be arranged in space in two different ways that are mirror images of each other, and which lead to so-called ''left-handed'' and ''right-handed'' versions (stereoisomers) of the same molecule. Molecules that cannot be superimposed on their own mirror image are said to be chiral; as the asymmetric carbon is the center of this chirality, it is also known as a chiral carbon. As an example, malic acid () has 4 carbon atoms but just one of them is asymmetric. The asymmetric carbon atom, bolded in the formula, is the one attached to two carbon atoms, an oxygen atom, and a hydrogen atom. One may initially be inclined to think this atom is not asymmetric because it is attached to two carbon atoms, but because those two carbon atoms are not attached to exactly the same things, there are two different '' ...
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Methyl Group
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bonded to the rest of the molecule by a single covalent bond (), it can be found on its own in any of three forms: methanide anion (), methylium cation () or methyl radical (). The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed. Methyl cation, anion, and radical Methyl cation The methylium cation () exists in the gas phase, but is otherwise not encountered. Some compounds are considered to be sources of the cation, and this simplification is used pervasively in organic chemistry. For ex ...
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Cycloheptane
Cycloheptane, also known as Suberane, is an Chemical compound, organic compound, which belongs to the group of cycloalkanes. The compound can occur in different Rotamer, conformers. Production Cycloheptane occurs naturally in petroleum and can be extracted from it. It is synthesized by a Clemmensen reduction from cycloheptanone. Properties Cycloheptane is a colorless liquid with a mild, aromatic odor. The boiling point at normal pressure is 119°C. The molar enthalpy of vaporization is 38.5 kJ mol−1. According to the Antoine equation, the vapor pressure function is given by log10(''P'') = ''A''−(''B''/(''T''+''C'')) (''P'' in bar, ''T'' in kelvins) with ''A'' = 3.97710, ''B'' = 1330.402 and ''C'' = −56.946 in the temperature range from 341.3 K to 432.2 K. In the solid phase, cycloheptane occurs in four Crystal polymorphism, polymorphic forms. The transformation temperatures for the conversion from form IV to form III are −138°C, from form III to form II −75°C and f ...
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Tomato
The tomato (, ), ''Solanum lycopersicum'', is a plant whose fruit is an edible Berry (botany), berry that is eaten as a vegetable. The tomato is a member of the nightshade family that includes tobacco, potato, and chili peppers. It originated from and was domesticated in western South America. It was introduced to the Old World by the Spanish in the Columbian exchange in the 16th century. Tomato plants are vines, largely Annual plant, annual and vulnerable to frost, though sometimes living longer in greenhouses. The flowers are able to self-fertilise. Modern varieties have been bred to ripen uniformly red, in a process that has impaired the fruit's sweetness and flavor. There are thousands of cultivars, varying in size, color, shape, and flavor. Tomatoes are attacked by many insect pests and nematodes, and are subject to diseases caused by viruses and by mildew and blight fungi. The tomato has a strong savoury umami flavor, and is an important ingredient in cuisines around ...
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Potato
The potato () is a starchy tuberous vegetable native to the Americas that is consumed as a staple food in many parts of the world. Potatoes are underground stem tubers of the plant ''Solanum tuberosum'', a perennial in the nightshade family Solanaceae. Wild potato species can be found from the southern United States to southern Chile. Genetic studies show that the cultivated potato has a single origin, in the area of present-day southern Peru and extreme northwestern Bolivia. Potatoes were domesticated there about 7,000–10,000 years ago from a species in the '' S. brevicaule'' complex. Many varieties of the potato are cultivated in the Andes region of South America, where the species is indigenous. The Spanish introduced potatoes to Europe in the second half of the 16th century from the Americas. They are a staple food in many parts of the world and an integral part of much of the world's food supply. Following millennia of selective breeding, there are now over 5 ...
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Datura
''Datura'' is a genus of nine species of highly poisonous, Vespertine (biology), vespertine-flowering plants belonging to the nightshade family (Solanaceae). They are commonly known as thornapples or jimsonweeds, but are also known as devil's trumpets or mad apple (not to be confused with angel's trumpets, which are placed in the closely related genus ''Brugmansia''). Other English common names include moonflower, devil's weed, and hell's bells. All species of ''Datura'' are extremely poisonous and Psychoactive plant, psychoactive, especially their seeds and flowers, which can cause respiratory depression, arrhythmias, fever, delirium, hallucinations, Toxidrome#Anticholinergic, anticholinergic toxidrome, psychosis, and death if taken internally. The name ''Datura'' originates from the Hindi and Sanskrit words for “thorn-apple,” with historical and cultural significance in Ayurveda and Hinduism, while the English term “Jimsonweed” derives from its prevalence in Jamestown, ...
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Deadly Nightshade
''Atropa bella-donna'', commonly known as deadly nightshade or belladonna, is a toxic perennial herbaceous plant in the nightshade family Solanaceae, which also includes tomatoes, potatoes and eggplant. It is native to Europe and Western Asia, including Turkey, its distribution extending from England in the west to western Ukraine and the Iranian province of Gilan in the east. It is also naturalised or introduced in some parts of Canada, North Africa and the United States. The foliage and berries are extremely toxic when ingested, containing tropane alkaloids. It can also be harmful to handle and/or touch these plants. These toxins include atropine, scopolamine, and hyoscyamine, which cause delirium and hallucinations, and are also used as pharmaceutical anticholinergics. Tropane alkaloids are of common occurrence not only in the Old World tribes Hyoscyameae (to which the genus Atropa belongs) and Mandragoreae, but also in the New World tribe Datureae—all of which ...
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Mandragora Officinarum
''Mandragora officinarum'' is the type species of the plant genus '' Mandragora'' in the nightshade family Solanaceae. It is often known as mandrake, although this name is also used for other plants. , sources differed significantly in the species they use for ''Mandragora'' plants native to the Mediterranean region. The main species found around the Mediterranean is called '' Mandragora autumnalis'', the autumn mandrake. In a broader circumscription, all the plants native to the regions around the Mediterranean Sea are placed in ''M. officinarum'', which thus includes ''M. autumnalis''. The names autumn mandrake and Mediterranean mandrake are then used. Whatever the circumscription, ''Mandragora officinarum'' is a perennial herbaceous plant with ovate leaves arranged in a rosette, a thick upright root, often branched, and bell-shaped flowers followed by yellow or orange berries. Because mandrakes contain deliriant hallucinogenic tropane alkaloids (atropine, scopolamin ...
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