Ergolines
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Ergolines
Ergoline is a chemical compound whose structural skeleton is contained in a variety of alkaloids, referred to as ergoline derivatives or ergoline alkaloids. Ergoline alkaloids, one being ergine, were initially characterized in ergot. Some of these are implicated in the condition ergotism, which can take a convulsive form or a gangrenous form. Even so, many ergoline alkaloids have been found to be clinically useful. Annual world production of ergot alkaloids has been estimated at 5,000–8,000 kg of all ergopeptines and 10,000–15,000 kg of lysergic acid, used primarily in the manufacture of semi-synthetic derivatives. Others, such as lysergic acid diethylamide, better known as LSD, a semi-synthetic derivative, and ergine, a natural derivative found in ''Argyreia nervosa'', ''Ipomoea tricolor'' and related species, are known psychedelic substances. Natural occurrence Ergoline alkaloids are found in lower fungi and some species of flowering plants: the Mexican species ...
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Lysergic Acid
Lysergic acid, also known as -lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and found in the seeds of '' Turbina corymbosa'' (ololiuhqui), '' Argyreia nervosa'' (Hawaiian baby woodrose), and ''Ipomoea tricolor'' (morning glories, tlitliltzin). Amides of lysergic acid, lysergamides, are widely used as pharmaceuticals and as psychedelic drugs (LSD). Lysergic acid is listed as a Table I precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances. Lysergic acid received its name as it was a product of the lysis of various ergot alkaloids. Total synthesis Lysergic acid is generally produced by hydrolysis of natural lysergamides, but can also be synthesized in the laboratory by a complex total synthesis, for example by Robert Burns Woodward's team in 1956. An enantioselective total synthesis based on a palladium-catalyzed domino cyclization r ...
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Ergot
Ergot ( ) or ergot fungi refers to a group of fungi of the genus ''Claviceps''. The most prominent member of this group is ''Claviceps purpurea'' ("rye ergot fungus"). This fungus grows on rye and related plants, and produces alkaloids that can cause ergotism in humans and other mammals who consume grains contaminated with its fruiting structure (called ''ergot sclerotium''). ''Claviceps'' includes about 50 known species, mostly in the tropical regions. Economically significant species include ''C. purpurea'' (parasitic on grasses and cereals), ''C. fusiformis'' (on pearl millet, buffel grass), ''C. paspali'' (on dallis grass), ''C. africana'' (on sorghum), and ''C. lutea'' (on paspalum). ''C. purpurea'' most commonly affects outcrossing species such as rye (its most common host), as well as triticale, wheat, and barley. It affects oats only rarely. ''C. purpurea'' has at least three races or varieties, which differ in their host specificity: *G1 — land grasses of open ...
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Ergonovine
Ergometrine, also known as ergonovine and sold under the brand names Ergotrate, Ergostat, and Syntometrine among others, is a medication used to cause contractions of the uterus to treat heavy vaginal bleeding after childbirth. It can be used either by mouth, by injection into a muscle, or injection into a vein. It begins working within 15 minutes when taken by mouth and is faster in onset when used by injection. Effects last between 45 and 180 minutes. Common side effect include high blood pressure, vomiting, seizures, headache, and low blood pressure. Other serious side effects include ergotism. It was originally made from the rye ergot fungus but can also be made from lysergic acid. Ergometrine is regulated because it can be used to make lysergic acid diethylamide (LSD). Ergometrine was discovered in 1932. It is on the World Health Organization's List of Essential Medicines. Medical uses Ergometrine has a medical use in obstetrics to facilitate delivery of the placenta a ...
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Lysergic Acid Diethylamide
Lysergic acid diethylamide (LSD), also known colloquially as acid, is a potent psychedelic drug. Effects typically include intensified thoughts, emotions, and sensory perception. At sufficiently high dosages LSD manifests primarily mental, visual, as well as auditory, hallucinations. Dilated pupils, increased blood pressure, and increased body temperature are typical. Effects typically begin within half an hour and can last for up to 20 hours. LSD is also capable of causing mystical experiences and ego dissolution. It is used mainly as a recreational drug or for spiritual reasons. LSD is both the prototypical psychedelic and one of the "classical" psychedelics, being the psychedelics with the greatest scientific and cultural significance. LSD is typically either swallowed or held under the tongue. It is most often sold on blotter paper and less commonly as tablets, in a watery solution or in gelatin squares called panes. LSD is considered to be non-addictive with low potent ...
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Ergine
Ergine, also known as d-lysergic acid amide (LSA) and d-lysergamide, is an ergoline alkaloid that occurs in various species of vines of the Convolvulaceae and some species of fungi. The psychedelic properties in the seeds of ololiuhqui, Hawaiian baby woodrose and morning glories have been linked to ergine and/or isoergine, its epimer, as it is an alkaloid present in the seeds. Occurrence in nature Ergine has been found in high concentrations of 20 μg/g dry weight in the sleepygrass infected with an ''Acremonium'' endophytic fungus together with other ergot alkaloids. Ergine is a component of the alkaloids contained in the ergot fungus, which grows on the heads of infected rye grasses. It is also found in the seeds of several varieties of morning glories in concentrations of approximately 10 μg per seed, as well as Hawaiian baby woodrose seeds, at a concentration of around 0.13% of dry weight. History ''Ololiuhqui'' was used by South American healers in shamanic ...
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Argyreia Nervosa
''Argyreia nervosa'' is a perennial climbing vine native to the Indian subcontinent and introduced to numerous areas worldwide, including Hawaii, Africa, and the Caribbean. Though it can be invasive, it is often prized for its aesthetic and medicinal value. Common names include Hawaiian baby woodrose, adhoguda अधोगुडा or vidhara विधारा (Sanskrit), elephant creeper and woolly morning glory. Its seeds are known for their powerful entheogenic properties, greater or similar to those of Ipomoea species, with users reporting significant psychedelic and spiritual experiences. The two botanical varieties are ''A. n.'' var. ''nervosa'' described here, and ''A. n.'' var. ''speciosa'', which are used in Ayurvedic medicine for their medicinal value. ''Argyreia nervosa'' seeds contain various ergoline alkaloids such as ergine. A study reported stereoisomers of ergine to be found in the seeds at a concentration of 0.325% of dry weight. A more recent study reported ...
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Ergotamine Tartrate
Ergotamine, sold under the brand names Cafergot (with caffeine) and Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It possesses structural similarity to several neurotransmitters, and has biological activity as a vasoconstrictor. It is used medicinally for treatment of acute migraine attacks (sometimes in combination with caffeine). Medicinal usage of ergot fungus began in the 16th century to induce childbirth, yet dosage uncertainties discouraged the use. It has been used to prevent post-partum hemorrhage (bleeding after childbirth). It was first isolated from the ergot fungus by Arthur Stoll at Sandoz in 1918 and marketed as Gynergen in 1921. Biosynthesis Ergotamine is a secondary metabolite (natural product) and the principal alkaloid produced by the ergot fungus, ''Claviceps purpurea'', and related fungi in the family Clavicipitaceae. Its biosynthesis in these fungi requir ...
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Alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.Chemical Encyclopedia: alkaloids
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Alkaloids are produced by a large variety of organisms including , , Medicinal plant, plants, an ...
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Chemical Structure
A chemical structure determination includes a chemist's specifying the molecular geometry and, when feasible and necessary, the electronic structure of the target molecule or other solid. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together, and can be represented using structural formulae and by molecular models; complete electronic structure descriptions include specifying the occupation of a molecule's molecular orbitals. Structure determination can be applied to a range of targets from very simple molecules (e.g., diatomic oxygen or nitrogen), to very complex ones (e.g., such as protein or DNA). Background Theories of chemical structure were first developed by August Kekulé, Archibald Scott Couper, and Aleksandr Butlerov, among others, from about 1858. These theories were first to state that chemical compounds are not a random cluster of atoms and functional groups, but rather had a definite order ...
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Arthur Stoll
Arthur Stoll (8 January 1887 – 13 January 1971) was a Swiss biochemist. Education and career The son of a teacher and school headmaster, he studied chemistry at the ETH Zurich, with a PhD in 1911, where he studied with Richard Willstätter. In 1912, he became a research assistant at the Kaiser Wilhelm Institute for Chemistry in Berlin, with Richard Willstätter, with whom he explored important insights on the importance of chlorophyll in carbon assimilation. In 1917, he was appointed professor of chemistry at the Ludwig Maximilian University of Munich. In the same year, he was hired as head of the pharmaceutical department of the Sandoz (now Novartis) chemical factory in Basel. In this company, he was president from 1949 to 1956, Director from 1964 he held the office of President of the Board. Together with Sandoz employees, he developed a range of methods for producing drugs. Thus, he developed the first isolation of ergot alkaloids (as ergotamine and ergobasine) and cardi ...
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Sandoz
Novartis AG is a Swiss-American multinational pharmaceutical corporation based in Basel, Switzerland and Cambridge, Massachusetts, United States (global research).name="novartis.com">https://www.novartis.com/research-development/research-locations It is one of the largest pharmaceutical companies in the world. Novartis manufactures the drugs clozapine (Clozaril), diclofenac (Voltaren; sold to GlaxoSmithKline in 2015 deal), carbamazepine (Tegretol), valsartan (Diovan), imatinib mesylate (Gleevec/Glivec), cyclosporine (Neoral/Sandimmune), letrozole (Femara), methylphenidate (Ritalin; production ceased 2020), terbinafine (Lamisil), deferasirox (Exjade), and others. In March 1996, the companies Ciba-Geigy and Sandoz merged to form Novartis; the pharmaceutical and agrochemical divisions of both companies formed Novartis as an independent entity. Other Ciba-Geigy and Sandoz businesses were sold, or, like Ciba Specialty Chemicals, spun off as independent companies. The Sandoz brand ...
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Vasoconstriction
Vasoconstriction is the narrowing of the blood vessels resulting from contraction of the muscular wall of the vessels, in particular the large arteries and small arterioles. The process is the opposite of vasodilation, the widening of blood vessels. The process is particularly important in controlling hemorrhage and reducing acute blood loss. When blood vessels constrict, the flow of blood is restricted or decreased, thus retaining body heat or increasing vascular resistance. This makes the skin turn paler because less blood reaches the surface, reducing the radiation of heat. On a larger level, vasoconstriction is one mechanism by which the body regulates and maintains mean arterial pressure. Medications causing vasoconstriction, also known as vasoconstrictors, are one type of medicine used to raise blood pressure. Generalized vasoconstriction usually results in an increase in systemic blood pressure, but it may also occur in specific tissues, causing a localized reduction in bl ...
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