Californidine

{{Chembox | ImageFile = Californidine.svg | ImageSize = 200px | PIN = (5''R'',12''S'')-15,15-Dimethyl-5,6,12,13-tetrahydro-2''H'',9''H''-[5,12-azanocycloocta[1,2-''f'':5,6-''f''′]bis([1,3]benzodioxol)]-15-ium | OtherNames = ''N''-Methylcalifornine; ''N''-Methylcrychine; ''N''-Methylescholtzine; Eschscholtzine ''N''-methosalt |Section1={{Chembox Identifiers | CASNo = 18830-99-4 | CASNo_Ref = {{cascite|correct|}} | PubChem = 177017 | ChemSpiderID = 28941458 | SMILES = C[N+]1([C@H]2Cc3cc4c(cc3[C@@H]1Cc5c2cc6c(c5)OCO6)OCO4)C | StdInChI = 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 | StdInChIKey = HFYKETHYKFKFQE-HOTGVXAUSA-N }} |Section2={{Chembox Properties | C=20|H=20|N=1|O=4 | Formula_Charge = +1 | MolarMass = | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''Californidine''' is an alkaloid with the molecular formula C₂₀H₂₀NO₄⁺. It has been isolated from extracts of the California poppy (''Eschscholzia californica''),<ref>{{Cite journal | title = Eschscholzia californica alkaloids |author1=Parfeinikov, S. A. |author2=Murav'eva, D. A. | journal = Khimiya Prirodnykh Soedinenii | year = 1983 | issue = 2 | pages = 242–243}}</ref><ref>{{Cite journal | title = A comparative investigation on alkaloid composition in different populations of Eschscholtzia californica |author1=Tome, Franca |author2=Colombo, Maria Laura |author3=Caldiroli, Luisa | journal = Phytochemical Analysis | year = 1999 | volume = 10 | issue = 5 | pages = 264–267 | doi = 10.1002/(SICI)1099-1565(199909/10)10:5<264::AID-PCA469>3.0.CO;2-4}}</ref> from which it gets its name, and from other plants of the genus ''Eschscholzia''.<ref>{{Cite journal | title = Alkaloids of Papaveraceae. XXXVI. Further alkaloids of Eschscholtzia douglasii and E. glauca, and on the constitution of californidine |author1=Slavik, Jiri |author2=Slavikova, L. |author3=Haisova, K. | journal = Collection of Czechoslovak Chemical Communications | year = 1967 | volume = 32 | issue = 12 | pages = 4420–4430}}</ref><ref>{{Cite journal | title = Alkaloids of the Papaveraceae. Part LXXXII. On alkaloids from the aerial parts of three Eschscholtzia species |author1=Slavik, Jiri |author2=Slavikova, Leonora | journal = Collection of Czechoslovak Chemical Communications | year = 1986 | volume = 51 | issue = 8 | pages = 1743–1751 | doi = 10.1135/cccc19861743}}</ref>

==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.<ref>{{cite journal | pmc=4609799 | year=2015 | last1=Fedurco | first1=M. | last2=Gregorová | first2=J. | last3=Šebrlová | first3=K. | last4=Kantorová | first4=J. | last5=Peš | first5=O. | last6=Baur | first6=R. | last7=Sigel | first7=E. | last8=Táborská | first8=E. | title=Modulatory Effects of Eschscholzia californica Alkaloids on Recombinant GABAA Receptors | journal=Biochemistry Research International | volume=2015 | article-number=617620 | doi=10.1155/2015/617620 | pmid=26509084 | doi-access=free }}</ref>

==References== {{reflist}}

Category:Quaternary ammonium compounds Category:Benzylisoquinoline alkaloids Category:Oxygen heterocycles