Names | |
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Preferred IUPAC name Octahydro-2H-quinolizine | |
Other names Norlupinane, quinolizidine | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C9H17N | |
Molar mass | 139.24 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Quinolizidine (norlupinane, octahydro-2H-quinolizine) is a nitrogen-containing heterocyclic compound. Some alkaloids (e.g. cytisine and sparteine) are derivatives of quinolizidine.
Quinolizidine alkaloids, such as nupharine and related chemicals, can be found in Nymphaea lotus and other species in the family Nymphaeaceae. Quinolizidine alkaloids are also found in genistoid legumes.
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.
Batrachotoxin (BTX) is an extremely potent cardio- and neurotoxic steroidal alkaloid found in certain species of beetles, birds, and frogs. The name is from the Greek word βάτραχος, bátrachos, 'frog'. Structurally-related chemical compounds are often referred to collectively as batrachotoxins. It is an extremely poisonous alkaloid. In certain frogs, this alkaloid is present mostly on the skin. Such frogs are among those used for poisoning darts. Batrachotoxin binds to, and irreversibly opens, the sodium channels of nerve cells and prevents them from closing, resulting in paralysis and death. No antidote is known.
Macromerine is a phenethylamine derivative. It was first identified from the cactus Coryphantha macromeris. It can also be found in C. runyonii, C. elephantidens, and other related members of the family Cactaceae. The plants may have been used by Tarahumara shamans for their entheogenic effects.
Lupinine is a quinolizidine alkaloid present in the genus Lupinus of the flowering plant family Fabaceae. The scientific literature contains many reports on the isolation and synthesis of this compound as well as a vast number of studies on its biosynthesis from its natural precursor, lysine. Studies have shown that lupinine hydrochloride is a mildly toxic acetylcholinesterase inhibitor and that lupinine has an inhibitory effect on acetylcholine receptors. The characteristically bitter taste of lupin beans, which come from the seeds of Lupinus plants, is attributable to the quinolizidine alkaloids which they contain, rendering them unsuitable for human and animal consumption unless handled properly. However, because lupin beans have potential nutritional value due to their high protein content, efforts have been made to reduce their alkaloid content through the development of "sweet" varieties of Lupinus.
Sparteine is a class 1a antiarrhythmic agent; a sodium channel blocker. It is an alkaloid and can be extracted from scotch broom. It is the predominant alkaloid in Lupinus mutabilis, and is thought to chelate the bivalent cations calcium and magnesium. It is not FDA approved for human use as an antiarrhythmic agent, and it is not included in the Vaughan Williams classification of antiarrhythmic drugs.
Allopumiliotoxins are a structural division in the pumiliotoxin-A class of alkaloids. The compounds of the pumiliotoxin-A class are primarily found in the skins of frogs, toads, and other amphibians and are used as a chemical defense mechanism to ward off predators, microorganisms, and ectoparasites. The compounds were originally discovered in neotropical dendrobatid frogs, but are also found in the mantellid frogs of Madagascar, myobatrachid frogs of Australia, and bufonid toad of South America. Frogs possessing this defense mechanism have aposematic coloring.
In enzymology, a 13-hydroxylupinine O-tigloyltransferase is an enzyme that catalyzes the chemical reaction
Sophora flavescens, the shrubby sophora, is a species of plant in the genus Sophora of the family Fabaceae. This genus contains about 52 species, nineteen varieties, and seven forms that are widely distributed in Asia, Oceania, and the Pacific islands. About fifteen of these species have a long history of use in traditional Chinese medicines.
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,
Sinomenine or cocculine is an alkaloid found in the root of the climbing plant Sinomenium acutum which is native to Japan and China. The plant is traditionally used in herbal medicine in these countries for rheumatism and arthritis. However, its analgesic action against other kinds of pain is limited. Sinomenine is a morphinan derivative, related to opioids such as levorphanol and the non-opioid cough suppressant dextromethorphan. Its anti-rheumatic effects are thought to be primarily mediated via release of histamine, but other effects such as inhibition of prostaglandin, leukotriene and nitric oxide synthesis may also be involved.
Pericine is one of a number of indole alkaloids found in the tree Picralima nitida, commonly known as akuamma. As with some other alkaloids from this plant such as akuammine, pericine has been shown to bind to mu opioid receptors in vitro, and has an IC50 of 0.6 μmol, within the range of a weak analgesic. It may also have convulsant effects.
Ibogamine is an anti-convulsant, anti-addictive, CNS stimulant alkaloid found in Tabernanthe iboga and Crepe Jasmine. Basic research related to how addiction affects the brain has used this chemical.
Gelsemine (C20H22N2O2) is an indole alkaloid isolated from flowering plants of the genus Gelsemium, a plant native to the subtropical and tropical Americas, and southeast Asia, and is a highly toxic compound that acts as a paralytic, exposure to which can result in death. It has generally potent activity as an agonist of the mammalian glycine receptor, the activation of which leads to an inhibitory postsynaptic potential in neurons following chloride ion influx, and systemically, to muscle relaxation of varying intensity and deleterious effect. Despite its danger and toxicity, recent pharmacological research has suggested that the biological activities of this compound may offer opportunities for developing treatments related to xenobiotic or diet-induced oxidative stress, and of anxiety and other conditions, with ongoing research including attempts to identify safer derivatives and analogs to make use of gelsemine's beneficial effects.
Nupharin may refer to:
Retama monosperma, the bridal broom or bridal veil broom, is a flowering bush species in the genus Retama, native to the western Mediterranean Basin.
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.
Dendrobine is an alkaloid found in Dendrobium nobile at an average of 0.5% by weight. It is a colorless solid at room temperature. It is related to the picrotoxin family of natural products. When given a fatal dose, death is usually caused by convulsions. It possesses a molecular structure that attracted interest in its total synthesis by organic chemists.
Rick L. Danheiser is an American organic chemist and is the Arthur C. Cope Professor of Chemistry at the Massachusetts Institute of Technology and Chair of the MIT Faculty. His research involves the invention of new methods for the synthesis of complex organic compounds. Danheiser is known for the Danheiser annulation and Danheiser benzannulation reactions.
Quinolizidine alkaloids are natural products that have a quinolizidine structure; this includes the lupine alkaloids.
Thomas Hartmann,, was a German pharmaceutical biologist and ecologist who was professor in the Department of Pharmaceutical Biology at the Technische Universität Braunschweig. His research focused on the biosynthesis, intracellular transport, and action of quinolizidine and pyrrolizidine alkaloids in fungi and plants and the sequestration of these secondary natural products by insects.