Lysergol
Chemical compound
From Wikipedia, the free encyclopedia
Lysergol is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi (most within Claviceps), and in the morning glory family of plants (Convolvulaceae), including the hallucinogenic seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea.
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| Names | |
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| IUPAC name
(6-Methyl-9,10-didehydroergolin-8β-yl)methanol | |
| Systematic IUPAC name
[(6aR,9R)-7-Methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl]methanol | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.009.113 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C16H18N2O | |
| Molar mass | 254.33 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lysergol can be synthesised using a tandem reaction to construct the piperidine skeleton and a rhodium-catalyzed [3 + 2] annulation in the late-stage indole formation.[1]
The binding of lysergol, as well as of isolysergol, to the serotonin 5-HT1A, 5-HT2A, 5-HT2B, and 5-HT2C receptors has been described.[2][3]
In contrast to LSD and other lysergamides, lysergol is non-hallucinogenic in humans and is described as not contributing to the hallucinogenic effects of morning glory seeds.[4][5][6] It was inactive as a hallucinogen at doses of 2 to 8 mg orally, up to more than 100 times the effective dosage of LSD, but did produce light sedative-like effects at the 8 mg dose.[4][6]
Lysergol is not a controlled substance in the United States. Its possession and sale is also legal under the U.S. Federal Analog Act because it does not have a known pharmacological action or a precursor relationship to LSD, which is a controlled substance. However, lysergol is an intermediate in the manufacture of some ergoloid medicines (e.g., nicergoline).