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]

Horticulturalist Alys Fowler wrote in 2022 that the California poppy "makes the most wonderful tea. You can use aerial parts: flowers, stems, leaves, fresh or dried. It is a gentle tea that can reduce anxiety and aid sleep. It contains none of the alkaloids associated with opium poppies." [6]

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 cup-shaped flowers in brilliant shades of red, orange and yellow. It is also used as food or a garnish. 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.

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

The Papaveraceae are an economically important family of about 42 genera and approximately 775 known species of flowering plants in the order Ranunculales, informally known as the poppy family. The family is cosmopolitan, occurring in temperate and subtropical climates, but 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.

<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 now is obscured by ancient introductions and cultivation, being naturalized across much of Europe and Asia.

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

Noscapine is a benzylisoquinoline alkaloid, of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the family Papaveraceae. It lacks significant hypnotic, euphoric, or analgesic effects affording it with very low addictive potential. This agent is primarily used for its antitussive (cough-suppressing) effects.

<i>Chelidonium majus</i> Species of flowering plant in the poppy family (Papaveraceae)

Chelidonium majus, the greater celandine, is a perennial herbaceous flowering plant in the poppy family Papaveraceae. One of two species in the genus Chelidonium, it is native to Europe and western Asia and introduced widely in North America.

<span class="mw-page-title-main">Poppy tea</span> Herbal tea made out of poppy straw or poppy seeds

Poppy tea is an herbal tea infusion brewed from poppy straw or seeds of several species of poppy. The species most commonly used for this purpose is Papaver somniferum, which produces opium as a natural defense against predators. In the live flower, opium is released when the surface of the bulb, called the seed pod, is pierced or scraped. For the purpose of the tea, dried pods are more commonly used than the pods of the live flower. The walls of the dried pods contain opiate alkaloids, primarily consisting of morphine.

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 Papaveraceae. 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.

<i>Glaucium flavum</i> Species of flowering plant

Glaucium flavum, the yellow horned poppy, yellow hornpoppy or sea poppy, is a summer flowering plant in the family Papaveraceae. It is native to Europe, Northern Africa, Macaronesia and temperate zones in Western Asia. The plant grows on the seashore and is never found inland. All parts of the plant, including the seeds, are toxic. It is classed as a noxious weed in some areas of North America, where it is an introduced species. It is grown in gardens as a short-lived perennial but usually grown as a biennial.

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

Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids

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

Glaucine(1,2,9,10-TetraMethoxyAporphine, Bromcholitin, Glauvent, Tusidil, Tussiglaucin) 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 like 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 arabicumArgemone mexicana, Eschscholtzia, Corydalis, Fumaria, Chelidonium, Hunnemannia fumariifoliaEschscholzia lobbii and more 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">Isoquinoline alkaloids</span>

Isoquinoline alkaloids are natural products of the group of alkaloids, which are chemically derived from isoquinoline. They form the largest group among the alkaloids.

<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.

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.
  6. "Now is the perfect time for some California poppy dreamin' | Alys Fowler". TheGuardian.com . 20 May 2022.