Cycloclavine
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, 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.