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| Names | |
|---|---|
| Systematic IUPAC name (8α)-6,8-Dimethyl-9,10-didehydroergolin-8-ol | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
PubChem CID | |
| UNII | |
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| Properties | |
| C16H18N2O | |
| Molar mass | 254.333 g·mol−1 |
| Appearance | prisms |
| Melting point | 229 to 234 [1] °C (444 to 453 °F; 502 to 507 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Setoclavine is an ergot alkaloid. [2]
Ergot or ergot fungi refers to a group of fungi of the genus Claviceps.
Ergotism is the effect of long-term ergot poisoning, traditionally due to the ingestion of the alkaloids produced by the Claviceps purpurea fungus—from the Latin noun clava meaning club, and the suffix -ceps meaning head, i.e. the purple club-headed fungus—that infects rye and other cereals, and more recently by the action of a number of ergoline-based drugs. It is also known as ergotoxicosis, ergot poisoning, and Saint Anthony's Fire.
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 the dominant alkaloid present in the seeds.
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.
Lysergic acid, also known as D-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, and Ipomoea tricolor. Amides of lysergic acid, lysergamides, are widely used as pharmaceuticals and as psychedelic drugs (LSD). Lysergic acid received its name as it was a product of the lysis of various ergot alkaloids.
Ergotamine 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.
Ergoloid mesylates (USAN), co-dergocrine mesilate (BAN) or dihydroergotoxine mesylate, trade name Hydergine, is a mixture of the methanesulfonate salts of three dihydrogenated ergot alkaloids.
D-Lysergic acid α-hydroxyethylamide, also known as D-lysergic acid methyl carbinolamide, is an alkaloid of the ergoline family, believed to be present in small amounts in various species in the Convolvulaceae (LSA), as well as some species of fungi.
Methylergometrine is a synthetic analogue of ergometrine, a psychedelic alkaloid found in ergot, and many species of morning glory. It is a member of the ergoline family and chemically similar to LSD, ergine, ergometrine, and lysergic acid. Due to its oxytocic properties, it has a medical use in obstetrics. According to Jonathan Ott, methylergonovine has LSD-like actions above 2 milligrams, due to its agonistic action at the 5HT2A-mGlu2 receptor protomers. Clinical efficacy occurs around 200 µg, ten times lower than the hallucinogenic threshold.
A sclerotium, plural sclerotia, is a compact mass of hardened fungal mycelium containing food reserves. One role of sclerotia is to survive environmental extremes. In some higher fungi such as ergot, sclerotia become detached and remain dormant until favorable growth conditions return. Sclerotia initially were mistaken for individual organisms and described as separate species until Louis René Tulasne proved in 1853 that sclerotia are only a stage in the life cycle of some fungi. Further investigation showed that this stage appears in many fungi belonging to many diverse groups. Sclerotia are important in the understanding of the life cycle and reproduction of fungi, as a food source, as medicine, and in agricultural blight management.
Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.
Claviceps purpurea is an ergot fungus that grows on the ears of rye and related cereal and forage plants. Consumption of grains or seeds contaminated with the survival structure of this fungus, the ergot sclerotium, can cause ergotism in humans and other mammals. C. purpurea most commonly affects outcrossing species such as rye, as well as triticale, wheat and barley. It affects oats only rarely.
Epichloë coenophiala is a systemic and seed-transmissible endophyte of tall fescue, a grass endemic to Eurasia and North Africa, but widely naturalized in North America, Australia and New Zealand. The endophyte has been identified as the cause of the "fescue toxicosis" syndrome sometimes suffered by livestock that graze the infected grass. Possible symptoms include poor weight gain, elevated body temperature, reduced conception rates, agalactia, rough hair coat, fat necrosis, loss of switch and ear tips, and lameness or dry gangrene of the feet. Because of the resemblance to symptoms of ergotism in humans, the most likely agents responsible for fescue toxicosis are thought to be the ergot alkaloids, principally ergovaline produced by E. coenophiala.
Dihydroergocristine is an ergot alkaloid. Alongside dihydroergocornine and dihydroergocryptine, it is one of the components of ergoloid mesylates.
Ergocryptine is an ergopeptine and one of the ergot alkaloids. It is isolated from ergot or fermentation broth and it serves as starting material for the production of bromocriptine.
Ergocornine or 12′-Hydroxy-2′,5′-α-bis(1-methyl-ethyl)ergotaman-3′,6′,18-trione or C31H39N5O5 is a crystalline ergopeptine and one of the ergot alkaloids separated from ergotoxine. It is also a dopamine receptor agonist. It was discovered by Albert Hofmann, the Swiss chemist who created LSD.
Ergovaline is an ergopeptine and one of the ergot alkaloids. It is usually found in endophyte-infected species of grass like Tall fescue or Perennial Ryegrass. It is toxic to cattle feeding on infected grass, probably because it acts as a vasoconstrictor.
Agroclavine belongs to the group of ergot alkaloids, such as ergotamine. Historically, the main use of agroclavine was to oxidize it to elymoclavine, which can then be used for ergot-based drug synthesis.
Elymoclavine is an ergot alkaloid. It can be produced from C. fusiformis from Pennisetum typhoideum. It is a precursor in the biosynthesis of D-(+)-lysergic acid. Ergot alkaloids are natural products derived from L-tryptophan. They are often toxic for humans and animals. Despite that they are also well known for their pharmacological activities.
Chanoclavine, also known as chanoclavin-l is a tri-cyclic ergot alkaloid (ergoline) isolate of certain fungi. It is mainly produced by members of the genus claviceps. Long used in traditional Chinese medicine, it was found in 1987 mouse studies to stimulate dopamine D2 receptors in the brain.
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