{{Use dmy dates|date=September 2024}} {{Chembox | ImageFile = Meteloidine.svg | ImageSize = 150px | ImageAlt = | IUPACName = [(6''R'',7''S'')-6,7-Dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (''E'')-2-methylbut-2-enoate | OtherNames = |Section1={{Chembox Identifiers | CASNo = 526-13-6 | CASNo_Ref = {{cascite|correct|CAS}} | ChEBI = 6800 | ChemSpiderID = 4445158 | KEGG = C10861 | UNII = JN0S84O367 | UNII_Ref = {{fdacite|correct|FDA}} | PubChem = 5281864 | SMILES = C/C=C(\C)/C(=O)OC1CC2[C@@H]([C@@H](C(C1)N2C)O)O | 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+ | InChIKey=YZFJTFVPCWEPND-JHOCIBHQSA-N }} |Section2={{Chembox Properties | C=13|H=21|N=1|O=4 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Meteloidine''' is an alkaloid found in some ''Brugmansia'' and ''Datura'' species.<ref>{{cite journal |pmid=6045963 |year=1967 |last1=Leete |first1=E |title=Biosynthesis of the tiglic acid moiety of meteloidine in Datura meteloides |journal=Tetrahedron Letters |volume=18 |pages=1727–30 |last2=Murrill |first2=J. B |doi=10.1016/s0040-4039(00)90710-x }}</ref> Its also found in ''Erythroxylum australe'' and is said to be cocaine-like alkaloid.<ref>{{Cite web |url=https://www.erowid.org/psychoactives/faqs/faq_natural_high_australia.shtml#COCAINE |title=Erowid Psychoactive Vaults : Australian Natural Highs FAQ }}</ref>
==Occurrence== The first report of the isolation from a natural source of meteloidine was in 1908 by Frank Lee Pyman and William Colebrook Reynolds<ref>{{cite journal |last1=Pyman |first1=Frank Lee |title=Meteloidine : A New Solanaceous Alkaloid |journal=Journal of the Chemical Society |date=1 January 1908 |volume=93 |issue=93 |pages=2077–2081 |doi=10.1039/CT9089302077 |url=https://pubs.rsc.org/en/content/articlepdf/1908/ct/ct9089302077 |access-date=11 September 2021 |url-access=subscription }}</ref> from the flowering plant ''Datura metel'' along Angelate ester and ''Datura meteloides'' (now reclassified as ''Datura innoxia'').<ref>{{cite journal |last1=Barclay |first1=Arthur S |title=New Considerations in an Old Genus: ''Datura'' |journal=Botanical Museum Leaflets, Harvard University |date=16 January 1959 |volume=18 |issue=6 |pages=245–272 |doi=10.5962/p.168515 |jstor=41762193 |s2cid=89207912 |doi-access=free }}</ref>
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'',<ref>{{cite journal |last1=Griffin |first1=W J |title=Alkaloids in ''Datura'', Section ''Brugmansia'' |journal=Planta Medica |date=1966 |volume=14 |issue=4 |pages=468–474 |doi=10.1055/s-0028-1100075 |bibcode=1966PlMed..14..468G |url=https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0028-1100075 |access-date=11 September 2021 |archive-date=11 September 2021 |archive-url=https://web.archive.org/web/20210911192409/https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0028-1100075 |url-status=live |url-access=subscription }}</ref> and in the roots of ''Datura leichhardtii'',<ref>{{cite journal |last1=Evans |first1=W C |title=Studies on ''Datura leichhardtii'' Muell. Ex Benth. |journal=Journal of Pharmacy and Pharmacology |date=1962 |volume=14 |issue=1 |pages=107T–110T |doi=10.1111/j.2042-7158.1962.tb10542.x |s2cid=85621808 |url=https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.1962.tb10542.x?__cf_chl_jschl_tk__=pmd_SJ0tRwXVzMp1DpWTN9MnMr1p9vUNQoOydtCHuJmGgzc-1631382946-0-gqNtZGzNAhCjcnBszQxR |access-date=11 September 2021 |archive-date=11 September 2021 |archive-url=https://web.archive.org/web/20210911192406/https://onlinelibrary.wiley.com/doi/abs/10.1111/j.2042-7158.1962.tb10542.x?__cf_chl_jschl_tk__=pmd_SJ0tRwXVzMp1DpWTN9MnMr1p9vUNQoOydtCHuJmGgzc-1631382946-0-gqNtZGzNAhCjcnBszQxR |url-status=live |url-access=subscription }}</ref> ''Brugmansia suaveolens'',<ref>{{cite journal |last1=Evans |first1=W C |title=Alkaloids of Datura suaveolens |journal=Phytochemistry |date=November 1972 |volume=11 |issue=11 |pages=3293–3298 |doi=10.1016/s0031-9422(00)86392-x |bibcode=1972PChem..11.3293E |url=https://www.sciencedirect.com/science/article/pii/S003194220086392X |access-date=11 September 2021 |url-access=subscription }}</ref> ''Anthocercis littorea'' and ''Anthocercis viscosa''<ref>{{cite journal |last1=El Imam |first1=Y |title=Tropane Alkaloids of Species of ''Anthocercis'', ''Cyphanthera'' and ''Crenidium'' |journal=Planta Medica |date=1984 |volume=50 |issue=1 |pages=86–87 |doi=10.1055/s-2007-969628 |pmid=17340258 |bibcode=1984PlMed..50...86E |url=https://dx.doi.org/10.1055/s-2007-969628 |access-date=11 September 2021 |archive-date=24 September 2024 |archive-url=https://web.archive.org/web/20240924111359/https://www.thieme-connect.de/DOI/DOI?10.1055/s-2007-969628 |url-status=live |url-access=subscription }}</ref> 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 Solanaceae family, but in only one species in the family ''Erythroxylaceae''.<ref>{{cite journal |last1=Johns |first1=S R |title=Meteloidine from ''Erythroxylum australe'' F. Muell |journal=Australian Journal of Chemistry |date=1967 |volume=20 |issue=6 |pages=1301–1302 |doi=10.1071/CH9671301 |url=https://www.publish.csiro.au/ch/pdf/CH9671301 |doi-access=free |access-date=11 September 2021 |archive-date=31 July 2021 |archive-url=https://web.archive.org/web/20210731135418/https://www.publish.csiro.au/CH/pdf/CH9671301 |url-status=live }}</ref>
== See also == * Daturadiol * Serpentine * Catuabine
==References== {{reflist}}
Category:Diols Category:Tropane alkaloids found in Solanaceae