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Not to be confused with Liserdol or Lisuride.
Lysergol
Names
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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.113 Edit this at Wikidata
PubChem CID
UNII
  • InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3/t10-,15-/m1/s1 checkY
    Key: BIXJFIJYBLJTMK-MEBBXXQBSA-N checkY
  • OC[C@@H]3/C=C2/c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C
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 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 is not a controlled substance in the USA. 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).

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]

See also

References

  1. ^ Yuan, Haosen; Guo, Zhixian; Luo, Tuoping (2017). "Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity". Organic Letters. doi: 10.1021/acs.orglett.6b03779. ISSN  1523-7060.

External links


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