Tropanes
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Tropanes
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 ...
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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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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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Deliriant
Deliriants are a subclass of hallucinogen. The term was coined in the early 1980s to distinguish these drugs from psychedelics such as LSD and dissociatives such as ketamine, due to their primary effect of causing delirium, as opposed to the more lucid and less disturbed states produced by other types of hallucinogens, where rational thought is better preserved (including the ability to distinguish hallucinations from reality). Duncan, D. F., and Gold, R. S. (1982). Drugs and the Whole Person. New York: John Wiley & Sons The term generally refers to anticholinergic drugs, which are substances that inhibit the function of the neurotransmitter acetylcholine. Common examples of deliriants include plants of the genera ''Datura'' and '' Brugmansia'', both containing scopolamine, as well as higher than recommended dosages of diphenhydramine (Benadryl). A number of plant deliriants such as that of the Solanaceae family, particularly in the Americas, have been used by some indi ...
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Tropane Alkaloids Biochemistry
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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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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Erythroxylum Coca
''Erythroxylum coca'' is one of two species of cultivated coca. Description The coca plant resembles a blackthorn bush, and grows to a height of . The branches are straight, and the leaves, which have a green tint, are thin, opaque, oval, and taper at the extremities. A marked characteristic of the leaf is an areolated portion bounded by two longitudinal curved lines, one line on each side of the midrib, and more conspicuous on the underside of the leaf. Coca plants are mainly found in Colombia. The flowers are small, and disposed in little clusters on short stalks; the corolla is composed of five yellowish-white petals, the anthers are heart-shaped, and the pistil consists of three carpels united to form a three-chambered ovary. The flowers mature into red berries. Unlike ''Erythroxylum novogranatense'', ''Erythroxylum coca'' requires very acidic soil conditions. Soil acidity and water acidity need to be below pH 5.5, with the optimal value being pH 3.5, similar to that of ...
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Ecgonine
Ecgonine (tropane derivative) is a tropane alkaloid found naturally in coca leaves. It has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance in many jurisdictions, as are some substances which can be used as precursors to ecgonine itself. Structurally, ecgonine is a cycloheptane derivative with a nitrogen bridge. It is obtained by hydrolysis of cocaine with acids or alkalis, and crystallizes with one molecule of water, the crystals melting at 198–199 °C. It is levorotary, and on warming with alkalis gives iso-ecgonine, which is dextrorotary. It is a tertiary base, and has the properties of an acid and an alcohol. It is the carboxylic acid corresponding to tropine, for it yields the same products on oxidation, and by treatment with phosphorus pentachloride is converted into anhydroecgonine, C9H13NO2, which, when heated to 280 °C with hydrochloric acid, eliminates carbon dioxide Carbo ...
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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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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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Solanoideae
Solanoideae is a subfamily of the flowering plant family Solanaceae, and is sister to the subfamily Nicotianoideae. Within Solanaceae, Solanoideae contains some of the most economically important genera and species, such as the tomato (''Solanum lycopersicum''), potato (''Solanum tuberosum''), eggplant or aubergine (''Solanum melongena''), chili and bell peppers (''Capsicum'' spp.), mandrakes ('' Mandragora'' spp.), and jimson weed ('' Datura stramonium''). This subfamily consists of several well-established tribes: Capsiceae, Datureae, Hyoscyameae, Juanulloeae, Lycieae, Nicandreae, Nolaneae, Physaleae, Solandreae, and Solaneae. The subfamily also contains the contended tribes Mandragoreae and Jaboroseae. Tribal relationships The relationship between the tribes has recently been well described. Nicandreae is the most basal tribe of the family, placing sister to the other 9 (or by some counts 11) tribes. Datureae lies sister to Nicandreae, Physaleae, Capsiceae, ...
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Brugmansia
''Brugmansia'' is a genus of seven species of flowering plants in the nightshade family Solanaceae. They are woody trees or shrubs, with pendulous flowers, and have no spines on their fruit. Their large, fragrant flowers give them their common name of angel's trumpets, adjacent to the nickname devil's trumpets of the closely related genus ''Datura''. ''Brugmansia'' species are among the most toxic of ornamental plants, containing tropane alkaloids of the type also responsible for the toxicity and deliriant effects of both jimsonweed and the infamous Atropa belladonna, deadly nightshade. All seven species are known only in horticulture, cultivation or as Escaped plant, escapees from cultivation, and no wild plants have ever been confirmed. They are therefore listed as Extinct in the Wild by the IUCN Red List, although they are popular ornamental plants and still exist wild outside their native range as introduced species. It is suspected that their extinction in the wild is due to ...
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Acetylcholine
Acetylcholine (ACh) is an organic compound that functions in the brain and body of many types of animals (including humans) as a neurotransmitter. Its name is derived from its chemical structure: it is an ester of acetic acid and choline. Parts in the body that use or are affected by acetylcholine are referred to as cholinergic. Acetylcholine is the neurotransmitter used at the neuromuscular junction. In other words, it is the chemical that motor neurons of the nervous system release in order to activate muscles. This property means that drugs that affect cholinergic systems can have very dangerous effects ranging from paralysis to convulsions. Acetylcholine is also a neurotransmitter in the autonomic nervous system, both as an internal transmitter for both the sympathetic nervous system, sympathetic and the parasympathetic nervous system, and as the final product released by the parasympathetic nervous system. Acetylcholine is the primary neurotransmitter of the parasympathet ...
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