Cycloclavine is an
ergot alkaloid. It was first isolated in 1969 from seeds of Ipomoea hildebrandtii vatke.[2] The first total synthesis of (±)-cycloclavine was published in 2008 by Szántay.[3] Further reports came from Wipf and Petronijevic,[4] Cao[5] and Brewer.[6] In 2016, Wipf and McCabe completed an 8-step asymmetric synthesis of (–)-cycloclavine,[7] and in 2018, they expanded this approach toward (+)-cycloclavine and a biological characterization of the binding profile of both
enantiomers on 16 brain receptors.[8] 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 therapeutic opportunities of
clavinealkaloid scaffolds.
^Stauffacher, D; Niklaus, P; Tscherter, H; Weber, H.P; Hofmann, A (1969). "Cycloclavin, ein neues alkaloid aus Ipomoea hildebrandtii vatke—71". Tetrahedron. 25 (24): 5879–87.
doi:
10.1016/S0040-4020(01)83095-7.
PMID5373534.
^Incze, M.; Dörnyei, G.; Moldvai, I.; Temesvári-Major, E.; Egyed, O.; Szántay, C. (2008). "New routes to clavine-type ergot alkaloids. Part 2: Synthesis of the last, so far not yet synthesized member of the clavine alkaloid family, (±)-cycloclavine". Tetrahedron. 64 (13): 2924–2929.
doi:
10.1016/j.tet.2008.01.101.