Structure via PubChem · Public domain (PubChem)
lysergol
Sign in to saveAlso known as lysergole, LOL, 9,10-Didehydro-6-methyl-8-hydroxymethylergoline, [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-yl]methanol
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.
Chemical data
- Formula
- C16H18N2O
- Molecular weight
- 254.33 g/mol
- IUPAC name
- [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methanol
- SMILES
- CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)CO
- InChIKey
- BIXJFIJYBLJTMK-MEBBXXQBSA-N
- XLogP
- 2.2
- Polar surface area
- 39.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
52 papers- Lysergol exerts potent antiviral activity against the emerging Oropouche virus in vitro.Antiviral research · 2025
- Lysergol monohydrate.Acta crystallographica. Section E, Structure reports online · 2012
- Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity.Organic letters · 2017
- Simultaneous quantification of berberine and lysergol by HPLC-UV: evidence that lysergol enhances the oral bioavailability of berberine in rats.Biomedical chromatography : BMC · 2012
- Antibacterial and synergy of clavine alkaloid lysergol and its derivatives against nalidixic acid-resistant Escherichia coli.Chemical biology & drug design · 2013
via PubMed
Wikidata facts
- Mass
- 254.141913
Show 5 more facts
- chemical formula
- C₁₆H₁₈N₂O
- canonical SMILES
- CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)CO
- isomeric SMILES
- CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)CO
- subject has role
- antipsychotics
- found in taxon
- Penicillium
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- External links
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.
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.
Excerpted from Wikipedia’s “lysergol” article, available under the CC BY-SA 4.0 licence.