Lysergic Acid Hydroxyethylamide
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Lysergic Acid Hydroxyethylamide
-Lysergic acid α-hydroxyethylamide (LSH, LAH), also known as -lysergic acid methyl carbinolamide, is an alkaloid of the ergoline family, believed to be present in small amounts in various species in the ''Convolvulaceae'' (morning glory), as well as some species of fungi. Chemistry The structure is similar to LSD, with the N,N- diethylamide group replaced by an ''N''- (1- hydroxyethyl)amide in -lysergic acid α-hydroxyethylamide. Pharmacology Effects One of the alkaloids in the seeds of ''Rivea corymbosa'' (Ololiuhqui), ''Argyreia nervosa'' (Hawaiian Baby Woodrose), and ''Ipomoea violacea'' (Tlitliltzin) are ergine (LSA) and isoergine (its epimer). The human activity of -lysergic acid α-hydroxyethylamide is unknown. Legality -lysergic acid α-hydroxyethylamide is unscheduled and uncontrolled in the United States, but possession and sales of it for human consumption could potentially be prosecuted under the Federal Analog Act because of its structural similariti ...
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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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Federal Analog Act
The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Controlled Substances Act#Schedule I controlled substances, Schedule I or Controlled Substances Act#Schedule II controlled substances, II to be treated as if it were listed in Schedule I, but only if intended for human consumption. These similar substances are often called designer drugs. The law's constitutionality has been questioned by now Supreme Court Justice Neil Gorsuch; its broad reach has been used to successfully prosecute possession of chemicals openly sold as dietary supplements and naturally contained in foods such as chocolate. Definition (32) *(A) Except as provided in subparagraph (C), the term ''controlled substance analogue'' means a substance - **(i) the chemical structure of which is substantially similar to the chemical structure of a controlled substance in schedule I or I ...
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Lysergamides
Amides of lysergic acid are collectively known as lysergamides, and include a number of compounds with potent agonist and/or antagonist activity at various serotonin and dopamine receptors. See also * Ergoline * Bromocriptine * Fumigaclavine C * Hydergine * Lisuride * Pergolide Pergolide, sold under the brand name Permax and Prascend (veterinary) among others, is an ergoline-based dopamine receptor agonist used in some countries for the treatment of Parkinson's disease. Parkinson's disease is associated with reduced do ... References {{Ergolines ...
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Tlitliltzin
''Ipomoea tricolor'', the Mexican morning glory or just morning glory, is a species of flowering plant in the family Convolvulaceae, native to the New World tropics, and widely cultivated and naturalised elsewhere. It is an herbaceous annual or perennial twining liana growing to tall. The leaves are spirally arranged, long with a long petiole. The flowers are trumpet-shaped, in diameter, most commonly blue with a white to golden yellow centre. Cultivation and uses In cultivation, the species is very commonly grown misnamed as ''Ipomoea violacea'', actually a different, though related, species. ''I. tricolor'' does not tolerate temperatures below , and so in temperate regions is usually grown as an annual. It is in any case a relatively short-lived plant. It prefers a warm, sheltered, sunny position such as a south- or west-facing wall. Ingesting any part of the plant may cause discomfort. Numerous cultivars of ''I. tricolor'' with different flower colours have been selecte ...
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Ololiuhqui
''Ipomoea corymbosa'' is a species of morning glory, native throughout Latin America from Mexico as far south as Peru and widely naturalised elsewhere. Its common names include Christmasvine, Christmaspops, and snakeplant. Description and names Known to natives of north and central Mexico by its Nahuatl name Ololiúqui (also spelled ololiuhqui or ololiuqui) and by the south eastern natives as xtabentún (in Mayan), it is a perennial climbing vine with white flowers, often grown as an ornamental plant. Its flowers secrete copious amount of nectar, and the honey that bees make from it is very clear and aromatic. It also grows in Cuba, where it usually blooms from early December to February. It is considered one of the main honey plants of the island. This plant is often used for purposes other than recreation, as natives of Mexico consider the powder produced from its seeds a tool for divination and communion with spirits. Because of the widespread use among native tribes, Colon ...
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Hawaiian Baby Woodrose
''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 pr ...
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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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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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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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Ergoline
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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Epimer
In stereochemistry, an epimer is one of a pair of diastereomers. The two epimers have opposite configuration at only one stereogenic center out of at least two. All other stereogenic centers in the molecules are the same in each. Epimerization is the interconversion of one epimer to the other epimer. Doxorubicin and epirubicin are two epimers that are used as drugs. Examples The stereoisomers β-D- glucopyranose and β-D- mannopyranose are epimers because they differ only in the stereochemistry at the C-2 position. The hydroxy group in β-D-glucopyranose is equatorial (in the "plane" of the ring), while in β-D-mannopyranose the C-2 hydroxy group is axial (up from the "plane" of the ring). These two molecules are epimers but, because they are not mirror images of each other, are not enantiomers. (Enantiomers have the same name, but differ in D and L classification.) They are also not sugar anomers, since it is not the anomeric carbon involved in the stereochemistry. Simila ...
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Ergoline
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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