Meteloidine
| |
| Names | |
|---|---|
| IUPAC name
[(6R,7S)-6,7-Dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (E)-2-methylbut-2-enoate
| |
| Identifiers | |
3D model (JSmol)
|
|
PubChemCID
|
|
| UNII | |
| |
| |
| Properties | |
| C13H21NO4 | |
| Molar mass | 255.314g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
| |
Meteloidineis analkaloidfound in someBrugmansiaandDaturaspecies.[1]Its also found inErythroxylum australeand is said to be cocaine-like alkaloid.[2]
Occurrence
[edit]The first report of the isolation from a natural source of meteloidine was in 1908 byFrank Lee PymanandWilliam Colebrook Reynolds[3]from the flowering plantDatura metelalongAngelateester andDatura meteloides(now reclassified asDatura innoxia).[4]
Meteloidine is primarily found insolanaceousplants, and in one species of genusErythroxylum.It has been found in the leaves and flowers ofBrugmansia × candida,[5]and in therootsofDatura leichhardtii,[6]Brugmansia suaveolens,[7]Anthocercis littoreaandAnthocercis viscosa[8]in minor quantities, and inAnthocercis genistoidesas its principalalkaloid.Meteloidine has been identified inErythroxylum australe,which is ofchemotaxonomicinterest as meteloidine has been found in a number of the Solanacae family, but in only one species in the familyErythroxylaceae.[9]
See also
[edit]References
[edit]- ^Leete, E; Murrill, J. B (1967). "Biosynthesis of the tiglic acid moiety of meteloidine in Datura meteloides".Tetrahedron Letters.18:1727–30.doi:10.1016/s0040-4039(00)90710-x.PMID6045963.
- ^"Erowid Psychoactive Vaults: Australian Natural Highs FAQ".
- ^Pyman, Frank Lee (1 January 1908)."Meteloidine: A New Solanaceous Alkaloid".Journal of the Chemical Society.93(93): 2077–2081.doi:10.1039/CT9089302077.Retrieved11 September2021.
- ^Barclay, Arthur S (16 January 1959)."New Considerations in an Old Genus:Datura".Botanical Museum Leaflets, Harvard University.18(6): 245–272.doi:10.5962/p.168515.JSTOR41762193.S2CID89207912.
- ^Griffin, W J (1966)."Alkaloids inDatura,SectionBrugmansia".Planta Medica.14(4): 468–474.doi:10.1055/s-0028-1100075.Archivedfrom the original on 11 September 2021.Retrieved11 September2021.
- ^Evans, W C (1962)."Studies onDatura leichhardtiiMuell. Ex Benth ".Journal of Pharmacy and Pharmacology.14(1): 107T–110T.doi:10.1111/j.2042-7158.1962.tb10542.x.S2CID85621808.Archivedfrom the original on 11 September 2021.Retrieved11 September2021.
- ^Evans, W C (November 1972)."Alkaloids of Datura suaveolens".Phytochemistry.11(11): 3293–3298.doi:10.1016/s0031-9422(00)86392-x.Retrieved11 September2021.
- ^El Imam, Y (1984)."Tropane Alkaloids of Species ofAnthocercis,CyphantheraandCrenidium".Planta Medica.50(1): 86–87.doi:10.1055/s-2007-969628.PMID17340258.Archivedfrom the original on 24 September 2024.Retrieved11 September2021.
- ^Johns, S R (1967)."Meteloidine fromErythroxylum australeF. Muell ".Australian Journal of Chemistry.20(6): 1301–1302.doi:10.1071/CH9671301.Archivedfrom the original on 31 July 2021.Retrieved11 September2021.