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EntityQ105178759· pop 9· linked from 359 articles

Wikidata facts

Mass
322.168127944
Show 4 more facts
chemical formula
C₂₀H₂₂N₂O₂
isomeric SMILES
C=C[C@]12CN(C)[C@@H]3[C@H]4CO[C@H](C[C@H]41)[C@]1(C(=O)Nc4ccccc41)[C@@H]32
canonical SMILES
C=CC12CN(C)C3C4COC(CC41)C1(C(=O)Nc4ccccc41)C32
Commons category
Gelsemine
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~14 min read

Article

15 sections
Contents
  • Natural sources
  • Chemistry
  • Summary of biological activities
  • History
  • Mechanisms of action
  • Toxicity and toxicology
  • Treatment
  • Chemical synthesis
  • Potential medical applications
  • Modern medical utility
  • Traditional medical uses
  • Popular culture
  • See also
  • References
  • Further reading

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.

==Natural sources== thumb|right|upright|alt=Picture of plant climbing a trellis, with dar green foliage, and numerous bright yellow flowers. | Example of a Gelsemium species, from which gelsemine is isolated Gelsemium sempervirens, its principal source in the Americas. Gelsemine is found in, and can be isolated from, the subtropical to tropical flowering plant genus Gelsemium, family Gelsemiaceae, which as of 2014 included five species, where G. sempervirens Ait., the type species, is prevalent in the Americas and G. elegans Benth. in China and East Asia. The species in the Americas, G. sempervirens, has a number of common names that include yellow or Carolina jasmine (or jessamine), gelsemium, evening trumpetflower, and woodbine. The plant genus is native to the subtropical and tropical Americas, e.g., in Mexico, Honduras, Guatemala, and Belize, as well as to China and southeast Asia. The species is prized for its "heavily fragrant yellow flowers," and has been cultivated since mid-seventeenth century (in Europe). It is found in southeastern and south-central states of the U.S., and as a garden plant in warmer areas where it can be trained to grow over arbors or to cover walls (see image).

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