Californidine

Last updated
Californidine
Californidine.svg
Names
Preferred IUPAC name
(5R,12S)-15,15-Dimethyl-5,6,12,13-tetrahydro-2H,9H-[5,12-azanocycloocta[1,2-f:5,6-f′]bis([1,3]benzodioxol)]-15-ium
Other names
N-Methylcalifornine; N-Methylcrychine; N-Methylescholtzine; Eschscholtzine N-methosalt
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C20H20NO4/c1-21(2)15-3-11-5-17-19(24-9-22-17)7-13(11)16(21)4-12-6-18-20(8-14(12)15)25-10-23-18/h5-8,15-16H,3-4,9-10H2,1-2H3/q+1/t15-,16-/m0/s1
    Key: HFYKETHYKFKFQE-HOTGVXAUSA-N
  • C[N+]1([C@H]2Cc3cc4c(cc3[C@@H]1Cc5c2cc6c(c5)OCO6)OCO4)C
Properties
C20H20NO4+1
Molar mass 338.382 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Californidine is an alkaloid with the molecular formula C20H20NO4+. It has been isolated from extracts of the California poppy (Eschscholzia californica), [1] [2] from which it gets its name, and from other plants of the genus Eschscholzia . [3] [4]

Pharmaceutical use

Because of the sedative, anxiolytic, and analgesic effects, the herb California Poppy (Amapola de California, Eschscholzia californica, Pavot d'Amérique, Pavot d'Or, Pavot de Californie, Poppy California, Yellow Poppy) is currently sold in pharmacies in many countries. [5]

Related Research Articles

<i>Eschscholzia californica</i> Species of flowering plant and state flower of California

Eschscholzia californica, the California poppy, golden poppy, California sunlight or cup of gold, is a species of flowering plant in the family Papaveraceae, native to the United States and Mexico. It is cultivated as an ornamental plant flowering in summer, with showy flowers in brilliant shades of red, orange and yellow. It is also used as food or a garnish. It had various uses in indigenous herbalism. It became the official state flower of California in 1903.

<span class="mw-page-title-main">Poppy</span> Species of flowering plant in the family Papaveraceae

A poppy is a flowering plant in the subfamily Papaveroideae of the family Papaveraceae. Poppies are herbaceous plants, often grown for their colourful flowers. One species of poppy, Papaver somniferum, is the source of the narcotic drug mixture opium, which contains powerful medicinal alkaloids such as morphine and has been used since ancient times as an analgesic and narcotic medicinal and recreational drug. It also produces edible seeds. Following the trench warfare in the poppy fields of Flanders, Belgium, during World War I, poppies have become a symbol of remembrance of soldiers who have died during wartime, especially in the UK, Canada, Australia, New Zealand and other Commonwealth realms.

<i>Eschscholzia</i> Genus of flowering plants in the poppy family Papaveracae

Eschscholzia is a genus of 12 annual or perennial plants in the Papaveraceae (poppy) family. The genus was named after the Baltic German/Imperial Russian botanist Johann Friedrich von Eschscholtz (1793–1831). All species are native to Mexico or the southern United States.

<span class="mw-page-title-main">Papaveraceae</span> Family of flowering plants

The Papaveraceae, informally known as the poppy family, are an economically important family of about 42 genera and approximately 775 known species of flowering plants in the order Ranunculales. The family is cosmopolitan, occurring in temperate and subtropical climates like Eastern Asia as well as California in North America. It is almost unknown in the tropics. Most are herbaceous plants, but a few are shrubs and small trees. The family currently includes two groups that have been considered to be separate families: Fumariaceae and Pteridophyllaceae. Papaver is the classical name for poppy in Latin.

<i>Papaver somniferum</i> Species of flowering plant in the family Papaveraceae

Papaver somniferum, commonly known as the opium poppy or breadseed poppy, is a species of flowering plant in the family Papaveraceae. It is the species of plant from which both opium and poppy seeds are derived and is also a valuable ornamental plant grown in gardens. Its native range was east of the Mediterranean Sea, but has since been obscured and vastly expanded by introduction and cultivation from ancient times to the present day, being naturalized across much of Europe and Asia.

<span class="mw-page-title-main">Noscapine</span> Chemical compound

Noscapine, also known as narcotine, nectodon, nospen, anarcotine and (archaic) opiane, is a benzylisoquinoline alkaloid of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the family Papaveraceae. It lacks effects associated with opioids such as sedation, euphoria, or analgesia (pain-relief) and lacks addictive potential. Noscapine is primarily used for its antitussive (cough-suppressing) effects.

Dihydrobenzophenanthridine oxidase is an enzyme. In the IUBMB Enzyme Nomenclature, dihydrobenzophenanthridine oxidase is EC 1.5.3.12.

<i>Romneya coulteri</i> Species of flowering plant in the poppy family Papaveraceae

Romneya coulteri, the Coulter's Matilija poppy or California tree poppy, is a perennial species of flowering plant in the poppy family (Papaveraceae0. Native to southern California, USA, and Baja California, Mexico, it grows in dry canyons in chaparral and coastal sage scrub plant communities, sometimes in areas recently burned. It is a popular ornamental plant, kept for its large, showy flowers.

<span class="mw-page-title-main">Berberine</span> Quaternary ammonium cation

Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids, occurring naturally as a secondary metabolite in some plants including species of Berberis, from which its name is derived.

<i>Papaver radicatum</i> Species of flowering plant in the poppy family Papaveraceae

Arctic poppy(Papaver radicatum) is a flowering plant in the Papaveraceae family. It may also be referred to as rooted poppy or yellow poppy. Arctic poppies grow in cold climate conditions and are found in arctic regions throughout the world. Arctic poppies have adaptations, such as heliotropism and physical characteristics, which help them survive in the harsh environment they grow in.

<i>Eschscholzia parishii</i> Species of flowering plant

Eschscholzia parishii, with the common name Parish's poppy, is an annual desert wildflower in the Poppy family (Papaveraceae), native to several North American desert regions.

<span class="mw-page-title-main">Glaucine</span> Chemical compound

Glaucine is an aporphine alkaloid found in several different plant species in the family Papaveraceae, such as Glaucium flavum, Glaucium oxylobum, and Corydalis yanhusuo, and in other plants such as Croton lechleri in the family Euphorbiaceae.

<span class="mw-page-title-main">Canadine</span> Chemical compound

(S)-Canadine, also known as (S)-tetrahydroberberine and xanthopuccine, is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is present in many plants from the family Papaveraceae, such as Corydalis yanhusuo and C. turtschaninovii.

<span class="mw-page-title-main">Allocryptopine</span> Chemical compound

Allocryptopine is a bioactive alkaloid found in plants of the Papaveraceae family, including Glaucium arabicum, Argemone mexicana, Eschscholtzia, Corydalis, Fumaria, Chelidonium, Hunnemannia fumariifolia, Eschscholzia lobbii and other Papaveraceae plants.

<span class="mw-page-title-main">Chelidonine</span> Chemical compound

Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity.

<span class="mw-page-title-main">BBE-like enzymes</span>

Berberine bridge enzyme-like form a subgroup of the superfamily of FAD-linked oxidases, structurally characterized by a typical fold observed initially for vanillyl-alcohol oxidase (VAO). This proteins are part of a multigene family (PF08031) that can be found in plants, fungi and bacteria.

<i>Papaver heterophyllum</i> Plant species

Papaver heterophyllum, previously known as Stylomecon heterophylla, and better known as the wind poppy, is a winter annual herbaceous plant. It is endemic to the western California Floristic Province and known to grow in the area starting from the San Francisco Bay Area of Central Western California southwards to northwestern Baja California, Mexico. Its main habitat is often described as mesic and shady, with loamy soils such as soft sandy loam, clay loam, and leaf mold loam.

<i>Papaver armeniacum</i> Species of plant in the genus Papaver

Papaver armeniacum, the Armenian poppy, is a species of flowering plant in the family Papaveraceae, native to the Caucasus region. It produces the benzylisoquinoline alkaloid armepavine.

<span class="mw-page-title-main">Corydalis Alkaloids</span>

Corydalis Alkaloids are categorized as natural products of the isoquinoline alkaloid type.

References

  1. Parfeinikov, S. A.; Murav'eva, D. A. (1983). "Eschscholzia californica alkaloids". Khimiya Prirodnykh Soedinenii (2): 242–243.
  2. Tome, Franca; Colombo, Maria Laura; Caldiroli, Luisa (1999). "A comparative investigation on alkaloid composition in different populations of Eschscholtzia californica". Phytochemical Analysis. 10 (5): 264–267. doi:10.1002/(SICI)1099-1565(199909/10)10:5<264::AID-PCA469>3.0.CO;2-4.
  3. Slavik, Jiri; Slavikova, L.; Haisova, K. (1967). "Alkaloids of Papaveraceae. XXXVI. Further alkaloids of Eschscholtzia douglasii and E. glauca, and on the constitution of californidine". Collection of Czechoslovak Chemical Communications. 32 (12): 4420–4430.
  4. Slavik, Jiri; Slavikova, Leonora (1986). "Alkaloids of the Papaveraceae. Part LXXXII. On alkaloids from the aerial parts of three Eschscholtzia species". Collection of Czechoslovak Chemical Communications. 51 (8): 1743–1751. doi:10.1135/cccc19861743.
  5. Fedurco, M.; Gregorová, J.; Šebrlová, K.; Kantorová, J.; Peš, O.; Baur, R.; Sigel, E.; Táborská, E. (2015). "Modulatory Effects of Eschscholzia californica Alkaloids on Recombinant GABAA Receptors". Biochemistry Research International. 2015: 617620. doi: 10.1155/2015/617620 . PMC   4609799 . PMID   26509084.