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Names | |
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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 | |
Identifiers | |
3D model (
JSmol)
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ChemSpider | |
PubChem
CID
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UNII | |
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).
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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 clavine alkaloid scaffolds.
![]() | |
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 | |
3D model (
JSmol)
|
|
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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 clavine alkaloid scaffolds.