Cycloclavine
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| IUPAC name
6,8-Dimethyl-8,10-cycloergoline
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| Systematic IUPAC name
(1aS,3aR,9bS)-1a,3-Dimethyl-1a,2,3,3a,4,6-hexahydro-1H-cyclopropa[c]indolo[4,3-ef]indole | |
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C16H18N2 | |
| Molar mass | 238.334 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Cycloclavine is a cyclopropanated ergot alkaloid. It was first isolated in 1969 from seeds of Ipomoea hildebrandtii. The first total synthesis of (±)-cycloclavine was published in 2008 by Szántay. Further reports came from Wipf and Petronijevic, Cao and Brewer. In 2016, Wipf and McCabe completed an 8-step asymmetric synthesis of (–)-cycloclavine, and in 2018, they expanded this approach toward (+)-cycloclavine and a biological characterization of the binding profile of both enantiomers on 16 brain receptors. Natural (+)- and unnatural (–)-cycloclavine demonstrated significant stereospecificity and unique binding profiles in comparison to LSD (lysergic acid diethylamide), psilocin, and DMT. Differential 5-HT receptor affinities, as well as novel sigma-1 receptor properties, suggest potential future medicinal uses of this unique plant alkaloid.