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| Names | |
|---|---|
| IUPAC name 8β-(Hydroxymethyl)-6-methyl-9,10-didehydroergolin-8α-ol | |
| Systematic IUPAC name (6aR,9S)-9-(Hydroxymethyl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-ol | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
PubChem CID | |
| UNII | |
| |
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| Properties | |
| C16H18N2O2 | |
| Molar mass | 270.332 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Penniclavine is an ergot alkaloid. [1]
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 clava "club" or clavus "nail" and -ceps for "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 an 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.
Ergotamine, sold under the brand names Cafergot 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.
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 various species in the Convolvulaceae, as well as some species of fungi. Morning glory heavenly blue and Hawaiian baby woodrose especially contain high amounts of LSH, with content varying between species and by how fresh.
Methylergometrine, also known as methylergonovine and sold under the brand name Methergine, is a medication of the ergoline and lysergamide groups which is used as an oxytocic in obstetrics and in the treatment of migraine. It reportedly produces psychedelic effects similar to those of lysergic acid diethylamide (LSD) at high doses.
A sclerotium, 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.
Metergoline, also known as methergoline and sold under the brand names Contralac (veterinary) and Liserdol (clinical), is a monoaminergic medication of the ergoline group which is used as a prolactin inhibitor in the treatment of hyperprolactinemia and to suppress lactation.
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 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.
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.
Epoxyagroclavine is an ergot alkaloid made by permafrost Penicillium.
Setoclavine is an ergot alkaloid.
Paliclavine is an ergot alkaloid precursor.
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