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Meteloidine

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Meteloidine
Names
IUPAC name octan-3-yl] (E)-2-methylbut-2-enoate
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
UNII
InChI
  • InChI=1S/C13H21NO4/c1-4-7(2)13(17)18-8-5-9-11(15)12(16)10(6-8)14(9)3/h4,8-12,15-16H,5-6H2,1-3H3/b7-4+/t8?,9?,10?,11-,12+Key: YZFJTFVPCWEPND-JHOCIBHQSA-N
SMILES
  • C/C=C(\C)/C(=O)OC1CC2((C(C1)N2C)O)O
Properties
Chemical formula C13H21NO4
Molar mass 255.314 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Meteloidine is an alkaloid found in some Brugmansia and Datura species. Its also found in Erythroxylum australe and is said to be cocaine-like alkaloid.

Occurrence

The first report of the isolation from a natural source of meteloidine was in 1908 by Frank Lee Pyman and William Colebrook Reynolds from the flowering plant Datura metel along Angelate ester and Datura meteloides (now reclassified as Datura innoxia).

Meteloidine is primarily found in solanaceous plants, and in one species of genus Erythroxylum. It has been found in the leaves and flowers of Brugmansia × candida, and in the roots of Datura leichhardtii, Brugmansia suaveolens, Anthocercis littorea and Anthocercis viscosa in minor quantities, and in Anthocercis genistoides as its principal alkaloid. Meteloidine has been identified in Erythroxylum australe, which is of chemotaxonomic interest as meteloidine has been found in a number of the Solanacae family, but in only one species in the family Erythroxylaceae.

See also

References

  1. 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. PMID 6045963.
  2. "Erowid Psychoactive Vaults : Australian Natural Highs FAQ".
  3. Pyman, Frank Lee (1 January 1908). "Meteloidine : A New Solanaceous Alkaloid". Journal of the Chemical Society. 93 (93): 2077–2081. doi:10.1039/CT9089302077. Retrieved 11 September 2021.
  4. 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. JSTOR 41762193. S2CID 89207912.
  5. Griffin, W J (1966). "Alkaloids in Datura, Section Brugmansia". Planta Medica. 14 (4): 468–474. doi:10.1055/s-0028-1100075. Archived from the original on 11 September 2021. Retrieved 11 September 2021.
  6. Evans, W C (1962). "Studies on Datura leichhardtii Muell. Ex Benth". Journal of Pharmacy and Pharmacology. 14 (1): 107T–110T. doi:10.1111/j.2042-7158.1962.tb10542.x. S2CID 85621808. Archived from the original on 11 September 2021. Retrieved 11 September 2021.
  7. Evans, W C (November 1972). "Alkaloids of Datura suaveolens". Phytochemistry. 11 (11): 3293–3298. doi:10.1016/s0031-9422(00)86392-x. Retrieved 11 September 2021.
  8. El Imam, Y (1984). "Tropane Alkaloids of Species of Anthocercis, Cyphanthera and Crenidium". Planta Medica. 50 (1): 86–87. doi:10.1055/s-2007-969628. PMID 17340258. Archived from the original on 24 September 2024. Retrieved 11 September 2021.
  9. Johns, S R (1967). "Meteloidine from Erythroxylum australe F. Muell". Australian Journal of Chemistry. 20 (6): 1301–1302. doi:10.1071/CH9671301. Archived from the original on 31 July 2021. Retrieved 11 September 2021.
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