Californidine

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]

Californidine
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
  • 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).
Infobox references

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]

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.
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