Meteloidine

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)
UNII
  • 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
  • C/C=C(\C)/C(=O)OC1CC2[C@@H]([C@@H](C(C1)N2C)O)O
Properties
C13H21NO4
Molar mass 255.314 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Meteloidine is an alkaloid found in some Brugmansia and Datura species.[1] Its also found in Erythroxylum australe and is said to be cocaine-like alkaloid.[2]

Occurrence

The first report of the isolation from a natural source of meteloidine was in 1908 by Frank Lee Pyman and William Colebrook Reynolds[3] from the flowering plant Datura metel along Angelate ester and Datura meteloides (now reclassified as Datura innoxia).[4]

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,[5] and in the roots of Datura leichhardtii,[6] Brugmansia suaveolens,[7] Anthocercis littorea and Anthocercis viscosa[8] 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.[9]

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.