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| Names | |
|---|---|
| IUPAC name [(6R,7S)-6,7-Dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (E)-2-methylbut-2-enoate | |
| Identifiers | |
3D model (JSmol) | |
PubChem CID | |
| UNII | |
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| Properties | |
| C13H21NO4 | |
| Molar mass | 255.314 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Meteloidine is an alkaloid found in some Brugmansia and Datura species. [1] Its also found in Erythroxylum australe and is said to be cocaine-like alkaloid. [2]
The first report of the isolation from a natural source of meteloidine was in 1908 by Frank Lee Pyman and William Colebrook Reynolds [3] from the flowering plant Datura metel along Angelate ester and Datura meteloides (now reclassified as Datura innoxia ). [4]
Meteloidine is primarily found in solanaceous plants, and in one species of genus Erythroxylum . It has been found in the leaves and flowers of Brugmansia candida , [5] and in the roots of Datura leichhardtii , [6] Brugmansia suaveolens , [7] Anthocercis littorea and Anthocercis viscosa [8] in minor quantities, and in Anthocercis genistoides as its principal alkaloid. Meteloidine has been identified in Erythroxylum australe, which is of chemotaxonomic interest as meteloidine has been found in a number of the Solanacae family, but in only one species in the family Erythroxylaceae . [9]
Datura is a genus of nine species of highly poisonous, 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. Other English common names include moonflower, devil's weed, and hell's bells. All species of Datura are extremely poisonous and psychoactive, especially their seeds and flowers, which can cause respiratory depression, arrhythmias, fever, delirium, hallucinations, anticholinergic syndrome, psychosis, and death if taken internally.
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.
The name Catuaba is used for the infusions of the bark of a number of trees native to Brazil. The most widely used barks are derived from the trees Trichilia catigua and Erythroxylum vaccinifolium. Other catuaba preparations use the bark of trees from the following genera or families: Anemopaegma, Ilex, Micropholis, Phyllanthus, Secondatia, Tetragastris and species from the Myrtaceae.
Datura innoxia, known as pricklyburr, recurved thorn-apple, downy thorn-apple, Indian-apple, lovache, moonflower, nacazcul, toloatzin, toloaxihuitl, tolguache or toloache, is a species of flowering plant in the family Solanaceae. It is more rarely called sacred datura, a common name which is applied more often to the closely related Datura wrightii. It is native to the Southwestern United States, Central and South America, and introduced in Africa, Asia, Australia and Europe. The scientific name is often cited as D. innoxia. When English botanist Philip Miller first described the species in 1768, he misspelled the Latin word innoxia (inoffensive) when naming it D. inoxia. The name Datura meteloides was for some time erroneously applied to some members of the species, but that name has now been abandoned.
Voacangine is an alkaloid found predominantly in the root bark of the Voacanga africana tree, as well as in other plants such as Tabernanthe iboga, Tabernaemontana africana, Trachelospermum jasminoides, Tabernaemontana divaricata and Ervatamia yunnanensis. It is an iboga alkaloid which commonly serves as a precursor for the semi-synthesis of ibogaine. It has been demonstrated in animals to have similar anti-addictive properties to ibogaine itself. It also potentiates the effects of barbiturates. Under UV-A and UV-B light its crystals fluoresce blue-green, and it is soluble in ethanol.
Mitraphylline, an oxindole derivative, is an active alkaloid in the leaves of the tree Mitragyna speciosa, commonly known as kratom. As a non-narcotic constituent, it also occurs to a significant amount in the bark of Uncaria tomentosa along with a number of isomeric alkaloids.
Anthocercis, commonly known as tailflower, is a genus of shrubs which are endemic to southern temperate Australia with the center of distribution in the South West Botanical Province of Western Australia. All species of Anthocercis contain tropane alkaloids, and have occasionally caused poisoning in children or been suspected of poisoning stock. Anthocercis is known as the only Solanaceous plant known to produce resin compounds on glandular trichomes.
Datura leichhardtii is a species of thorn apple in the genus Datura. In 1844, Ludwig Leichhardt discovered this species in Australia. Ferdinand von Mueller gave it the name Datura leichhardtii when he published his first description of it in 1855.
Brugmansia suaveolens, Brazil's white angel trumpet, also known as angel's tears and snowy angel's trumpet, is a species of flowering plant in the nightshade family Solanaceae, native to south eastern Brazil, but thought to be extinct in the wild. Like several other species of Brugmansia, it exists as an introduced species in areas outside its native range. It is a tender shrub or small tree with large semi-evergreen leaves and fragrant yellow or white trumpet-shaped flowers.
Akuammine (vincamajoridine) is an indole alkaloid. It is the most abundant alkaloid found in the seeds from the tree Picralima nitida, commonly known as akuamma, comprising 0.56% of the dried powder. It has also been isolated from Vinca major. Akuammine is structurally related to yohimbine, mitragynine and more distantly Voacangine, all of which are alkaloid plant products with pharmacological properties.
Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids 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.
Hodgkinsine is an alkaloid found in plants of the genus Psychotria, particularly Psychotria colorata, although it is also found in Psychotria lyciiflora and probably other species in this family,
Nantenine is an alkaloid found in the plant Nandina domestica as well as some Corydalis species. It is an antagonist of both the α1-adrenergic receptor and the serotonin 5-HT2A receptor, and blocks both the behavioral and physiological effects of MDMA in animals.
The biosynthesis of cocaine has long attracted the attention of biochemists and organic chemists. This interest is partly motivated by the strong physiological effects of cocaine, but a further incentive was the unusual bicyclic structure of the molecule. The biosynthesis can be viewed as occurring in two phases, one phase leading to the N-methylpyrrolinium ring, which is preserved in the final product. The second phase incorporates a C4 unit with formation of the bicyclic tropane core.
Huáng bǎi, huáng bó or huáng bò is one of the fifty fundamental herbs of traditional Chinese medicine. Known also as Cortex Phellodendri, it is the bark of one of two species of Phellodendron tree: Phellodendron amurense or Phellodendron chinense.
Jatrorrhizine is a protoberberine alkaloid found in some plant species, such as Enantia chlorantha (Annonaceae). Synonyms that may be encountered include jateorrhizine, neprotin, jatrochizine, jatrorhizine, and yatrorizine.
Matrine is an alkaloid found in plants from the genus Sophora. It has a variety of pharmacological effects, including anti-cancer effects, as well as κ-opioid and μ-opioid receptor agonism.
Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida, Vinca minor and the Aspidosperma.
Brunfelsamidine is a poisonous pyrrolidine occurring in several species belonging to the Solanaceous genus Brunfelsia, which has convulsant and neurotoxic effects. It is a fairly common cause of poisoning among domestic animals such as cows and dogs that eat the plant. Symptoms are similar to poisoning from strychnine and can last from a few hours up to several days. It is also a weak tryptase inhibitor and found in Leptonychia pubescens
The Solanaceae, or the nightshades, are a family of flowering plants that ranges from annual and perennial herbs to vines, lianas, epiphytes, shrubs, and trees, and includes a number of agricultural crops, medicinal plants, spices, weeds, and ornamentals. Many members of the family contain potent alkaloids, and some are highly toxic, but many—including tomatoes, potatoes, eggplant, bell and chili peppers—are used as food. The family belongs to the order Solanales, in the asterid group and class Magnoliopsida (dicotyledons). The Solanaceae consists of about 98 genera and some 2,700 species, with a great diversity of habitats, morphology and ecology.
