Californidine

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
CAS Number	18830-99-4  Y
3D model (JSmol)	Interactive image
ChemSpider	28941458
PubChem CID	177017
CompTox Dashboard (EPA)	DTXSID10904141
InChI 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
SMILES C[N+]1([C@H]2Cc3cc4c(cc3[C@@H]1Cc5c2cc6c(c5)OCO6)OCO4)C
Properties
Chemical formula	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

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]

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.