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Tropane
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 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 a ...) is known as nortropane or nor-tropane. See also * Phenyltropane * Tropane alkaloid ...
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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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Solanaceae
Solanaceae (), commonly known as the nightshades, is a family of flowering plants in the order Solanales. It contains approximately 2,700 species, several of which are used as agricultural crops, medicinal plants, and ornamental plants. Many members of the family have high alkaloid contents, making some highly toxic, but many—such as tomatoes, potatoes, eggplants, and peppers—are commonly used in food. Originating in South America, Solanaceae now inhabits every continent on Earth except Antarctica. After the K—Pg extinction event they rapidly diversified and have adapted to live in deserts, tundras, rainforests, plains, and highlands, and taken on wide range of forms including trees, vines, shrubs, and epiphytes. Nearly 80% of all nightshades are included in the subfamily Solanoideae, most of which are members of the type genus ''Solanum''. Most taxonomists recognize six other subfamilies: Cestroideae, Goetzeoideae, Nicotianoideae, Petunioideae, Schizanthoideae, an ...
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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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Cocaine
Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, ''Erythroxylum coca'' and ''Erythroxylum novogranatense, E. novogranatense'', which are cultivated almost exclusively in the Andes. Indigenous peoples of South America, Indigenous South Americans have traditionally used coca leaves for over a thousand years. Notably, there is no evidence that habitual coca leaf use causes addiction or withdrawal, unlike cocaine. Medically, cocaine is rarely employed, mainly as a topical medication under controlled settings, due to its high abuse potential, adverse effects, and expensive cost. Despite this, recreational drug use, recreational use is widespread, driven by its euphoric and aphrodisiac properties. Levamisole induced necrosis syndrome (LINES)-a complication of the common cocaine Lacing (drugs), cutting agent levamisole-and prenatal cocaine exposure is particularly harmful. Street cocaine is ...
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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 varying, ...
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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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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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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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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 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. Occurrence Tropine is a natural product found in the plants of deadly nightshade (Atropa belladonna) and devil's trumpet (Datura stramonium). Chemistry Synthesis It can be prepared by hydrolysis of atropine or other solanaceous alkaloids. 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 trop ...
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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 dry mouth, abnormally large pupils, urinary retention, constipation, and a fast heart rate. It should generally not be used in people with closed-angle glaucoma. While there is no evidence that its use during pregnancy causes birth defects, this has not been well studied so sound clinical judgment should be used. It is likely safe during breastfeeding. It is an antimuscarinic (a type of anticholinergic) that works by inhibit ...
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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. Coca leaves contain cocaine which acts as a mild stimulant when chewed or consumed as tea, with slower absorption than purified cocaine and no evidence of addiction or withdrawal symptoms from natural use. The coca plant is a shrub-like bush with curved branches, oval leaves featuring distinct curved lines, small yellowish-white flowers that develop into red berries. Genomic analysis reveals that coca, a culturally and economically important plant, was domesticated two or three separate times from the wild species ''Erythroxylum gracilipes'' by different South American groups during the Holocene. Chewing coca in South America began at least 8,000 years ago, as evidenced by coca leaves and calcite found in house floors in Peru’s Nanchoc Valley, suggesting early communal use alongside the rise of farming. ...
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