Cycloclavine

Cycloclavine is a cyclopropanated ergot alkaloid. It was first isolated in 1969 from seeds of Ipomoea hildebrandtii.^[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 medicinal uses of this unique plant alkaloid.

Quick facts Names, Identifiers ...

Cycloclavine

Names
IUPAC name 6,8-Dimethyl-8,10-cycloergoline
Systematic IUPAC name (1aS,3aR,9bS)-1a,3-Dimethyl-1a,2,3,3a,4,6-hexahydro-1H-cyclopropa[c]indolo[4,3-ef]indole
Identifiers
CAS Number	26057-57-8[1] N
3D model (JSmol)	Interactive image
ChemSpider	25991549
PubChem CID	101316916
UNII	XRQ6TJ7KL8 Y
CompTox Dashboard (EPA)	DTXSID701045769
InChI InChI=1S/C16H18N2/c1-15-8-16(15)11-4-3-5-12-14(11)10(7-17-12)6-13(16)18(2)9-15/h3-5,7,13,17H,6,8-9H2,1-2H3/t13-,15-,16-/m0/s1 Key: ZWJHDICNUKHUGE-BPUTZDHNSA-N
SMILES [H][C@@]12CC3=CNC4=C3C(=CC=C4)[C@]11C[C@]1(C)CN2C
Properties
Chemical formula	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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