Tropane Alkaloids
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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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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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Isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the existence or possibility of isomers. Isomers do not necessarily share similar chemical property, chemical or physical property, physical properties. Two main forms of isomerism are structural isomerism, structural (or constitutional) isomerism, in which ''chemical bond, bonds'' between the atoms differ; and stereoisomerism (or spatial isomerism), in which the bonds are the same but the ''relative positions'' of the atoms differ. Isomeric relationships form a hierarchy. Two chemicals might be the same constitutional isomer, but upon deeper analysis be stereoisomers of each other. Two molecules that are the same stereoisomer as each other might be in different conformational forms or be different Isotopologue, isotopologues. The depth of analy ...
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Benzoylecgonine
Benzoylecgonine is the main metabolite of cocaine, formed by the liver and excreted in the urine. It is the compound tested for in most cocaine urine drug screens and in wastewater screenings for cocaine use. Biochemistry and physiology Chemically, benzoylecgonine is the benzoate ester of ecgonine. It is a primary metabolite of cocaine, and is pharmacologically inactive. It is the corresponding carboxylic acid of cocaine, its methyl ester. It is formed in the liver by the metabolism of cocaine by hydrolysis, catalysed by carboxylesterases, and subsequently excreted in the urine. It is readily synthesised by boiling cocaine freebase in water. Urinalysis Benzoylecgonine is the compound tested for in most substantive cocaine drug urinalyses. Presence in drinking water Benzoylecgonine is sometimes found in drinking water supplies. In 2005, scientists found large quantities of benzoylecgonine in Italy's Po River and used its concentration to estimate the number of cocaine users ...
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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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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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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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Stimulant
Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, Mood disorder, mood, and physical activity, physical performance. Some stimulants occur naturally, while others are exclusively synthetic. Common stimulants include caffeine, nicotine, amphetamines, cocaine, methylphenidate, and modafinil. Stimulants may be subject to varying forms of regulation, or outright prohibition, depending on jurisdiction. Stimulants increase activity in the sympathetic nervous system, either directly or indirectly. Prototypical stimulants increase synaptic concentrations of neurotransmitter, excitatory neurotransmitters, particularly norepinephrine and dopamine (e.g., methylphenidate). Other stimulants work by binding to the Receptor (biochemistry), receptors of excitatory neurotransmitters (e.g., nicotine) or by ...
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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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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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Hyoscine Hydrobromide
Scopolamine, also known as hyoscine, or Devil's Breath, is a medication used to treat motion sickness and postoperative nausea and vomiting. It is also sometimes used before surgery to decrease saliva. When used by injection, effects begin after about 20 minutes and last for up to 8 hours. It may also be used orally and as a transdermal patch since it has been long known to have transdermal bioavailability. Scopolamine is in the antimuscarinic family of drugs and works by blocking some of the effects of acetylcholine within the nervous system. Scopolamine was first written about in 1881 and started to be used for anesthesia around 1900. Scopolamine is also the main active component produced by certain plants of the nightshade family, which historically have been used as psychoactive drugs, known as '' deliriants'', due to their antimuscarinic-induced hallucinogenic effects in higher doses. In these contexts, its mind-altering effects have been utilized for re ...
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