Tropane
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Tropane
Tropane is a nitrogenous Bicyclic molecule, 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 Mandragora officinarum, 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[3.2.1]octane (tropane without the ''N''-methyl group) is known as nortropane or nor-tropane. See also * Phenyltropane * Tropane alkaloid * Tropine References

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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. Although RTI holds a strong position in this field, they are not the ''only'' researchers that have prepared these analogues. 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 ar ...
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Solanaceae
The Solanaceae , or nightshades, are a family of flowering plants that ranges from annual and perennial herbs to vines, lianas, epiphytes, shrubs, and trees, and includes a number of agricultural crops, medicinal plants, spices, weeds, and ornamentals. Many members of the family contain potent alkaloids, and some are highly toxic, but many—including tomatoes, potatoes, eggplant, bell and chili peppers—are used as food. The family belongs to the order Solanales, in the asterid group and class Magnoliopsida ( dicotyledons). The Solanaceae consists of about 98 genera and some 2,700 species, with a great diversity of habitats, morphology and ecology. The name Solanaceae derives from the genus ''Solanum''. The etymology of the Latin word is unclear. The name may come from a perceived resemblance of certain solanaceous flowers to the sun and its rays. At least one species of ''Solanum'' is known as the "sunberry". Alternatively, the name could originate from the Latin verb ''sol ...
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Tropane Alkaloid
Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids 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, racemate, 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''). * Hyoscine hydrobromide, Scopolamine, from henbane and ''Datura'' species (Jimson weed) All three acetylcholine-inhibiting chemicals can also be found in the leave ...
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Cocaine
Cocaine (from , from , ultimately from Quechuan languages, Quechua: ''kúka'') is a central nervous system (CNS) stimulant mainly recreational drug use, used recreationally for its euphoria, euphoric effects. It is primarily obtained from the leaves of two Coca species native to South America, ''Erythroxylum coca'' and ''Erythroxylum novogranatense''. After extraction from coca leaves and further processing into cocaine hydrochloride (powdered cocaine), the drug is often Insufflation (medicine), snorted, applied topical administration, topically to the mouth, or dissolved and injection (medicine), injected into a vein. It can also then be turned into free base form (crack cocaine), in which it can be heated until sublimated and then the vapours can be smoking, inhaled. Cocaine stimulates the mesolimbic pathway, reward pathway in the brain. Mental effects may include an euphoria, intense feeling of happiness, sexual arousal, psychosis, loss of contact with reality, or psychomo ...
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Tropane Alkaloids
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 v ...
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Deadly Nightshade
''Atropa belladonna'', commonly known as belladonna or deadly nightshade, is a toxic perennial herbaceous plant in the nightshade family Solanaceae, which also includes tomatoes, potatoes, and eggplant (aubergine). It is native to Europe, North Africa, and Western Asia. Its distribution extends from Great Britain 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 and the United States. The foliage and berries are extremely toxic when ingested, containing tropane alkaloids. 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 belong to the subfamily Solanoideae of the plant family Solanaceae. ''A ...
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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, scopolamine, ...
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Datura
''Datura'' is a genus of nine species of highly poisonous, 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 (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 potentially psychoactive, especially their seeds and flowers, which can cause respiratory depression, arrhythmias, fever, delirium, hallucinations, anticholinergic syndrome, psychosis, and even death if taken internally. Due to their effects and symptoms, they have occasionally been used not only as poisons, but also as hallucinogens by various groups throughout history. Traditionally, psychoactive administration of ''Datura'' species has often been associated with witchcraft and sorcery or similar practices in man ...
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Henbane
''Hyoscyamus niger'', commonly known as henbane, black henbane, or stinking nightshade, is a poisonous plant in the nightshade family Solanaceae. It is native to temperate Europe and Siberia, and naturalised in Great Britain and Ireland. Historical use The name ''henbane'' dates at least to AD 1265. The origins of the word are unclear, but "hen" probably originally meant death rather than referring to chickens. Other etymologies of the word associate it with the Indo-European stem ''*bhelena'' whose hypothetical meaning is 'crazy plant' and with the Proto-Germanic element ''bil'' meaning ‘vision, hallucination; magical power, miraculous ability’. Henbane was historically used in combination with other plants, such as mandrake, deadly nightshade, and datura, as an anaesthetic potion, as well as 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 ...
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Tropine
Tropine is a derivative of tropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol. Tropine is a central building block of many chemicals active in the nervous system, including tropane alkaloids. Some of these compounds, such as long-acting muscarinic antagonists are used as medicines because of these effects. Chemistry Synthesis It can be prepared by hydrolysis of atropine. See also * Pseudotropine * Atropine * Tropinone * 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 alkal ... References Tropanes Secondary alcohols {{heterocyclic-stub ...
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Atropine
Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically given intravenously or by injection into a muscle. Eye drops are also available which are used to treat uveitis and early amblyopia. The intravenous solution usually begins working within a minute and lasts half an hour to an hour. Large doses may be required to treat some poisonings. Common side effects include a dry mouth, large pupils, urinary retention, constipation, and a fast heart rate. It should generally not be used in people with angle closure glaucoma. While there is no evidence that its use during pregnancy causes birth defects, that has not been well studied. It is likely safe during breastfeeding. It is an antimuscarinic (a type of anticholinergic) that works by inhibiting the parasympathetic nervous system. Atropine occurs n ...
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Coca
Coca is any of the four cultivated plants in the family Erythroxylaceae, native to western South America. Coca is known worldwide for its psychoactive alkaloid, cocaine. The plant is grown as a cash crop in the Argentine Northwest, Bolivia, Alto Rio Negro Territory in Brazil, Colombia, Venezuela, Ecuador, and Peru, even in areas where its cultivation is unlawful. There are some reports that the plant is being cultivated in the south of Mexico, by using seeds imported from South America, as an alternative to smuggling its recreational product cocaine. It also plays a role in many traditional Amazonian and Andean cultures as well as the Sierra Nevada de Santa Marta in northern Colombia. The cocaine alkaloid content of dry ''Erythroxylum coca'' var. ''coca'' leaves was measured ranging from 0.23% to 0.96%. Coca-Cola used coca leaf extract in its products from 1885 until about 1903, when it began using decocainized leaf extract. Extraction of cocaine from coca requires several sol ...
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