Lysergol

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Lysergol
Lysergol.svg
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 OOjs UI icon edit-ltr-progressive.svg
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 Yes check.svgY
    Key: BIXJFIJYBLJTMK-MEBBXXQBSA-N Yes check.svgY
  • 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 .

Contents

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).

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.
  2. ↑ "Selective psychedelic compounds". Google Patents. 21 June 2022. Retrieved 18 March 2025.
  3. ↑ Tasker NR, Wipf P (October 2022). "A Short Synthesis of Ergot Alkaloids and Evaluation of the 5-HT1/2 Receptor Selectivity of Lysergols and Isolysergols". Org Lett. 24 (40): 7255–7259. doi:10.1021/acs.orglett.2c02569. PMID   35993579.
  4. 1 2 Fanchamps A (1978). "Some Compounds With Hallucinogenic Activity". In Berde B, Schild HO (eds.). Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). Vol. 49. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 567–614. doi:10.1007/978-3-642-66775-6_8. ISBN   978-3-642-66777-0. Lysergol (No. 79a) has no effect up to 6 mg, but 8 mg produce a slight sedation (HELM et al., 1968). [...] Table 2. Psychotomimetic activity and some pharmacodynamic effects of structural analogues of LSD [...]
  5. ↑ Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN   978-0-85608-011-1. OCLC   2176880. OL   4850660M. d-Lysergic acid amide (ergine) is the major constituent of the seeds of both Rivea corymbosa and Ipomoea violacea, together with smaller amounts of d-isolysergic acid amide (isoergine), chanoclavine, elymoclavine, and the N-(1-hydroxyethyl)amides of lysergic and isolysergic acids. [...] It is clear that the pharmacologically active constituents of ololiuqui are the isomeric lysergic acid amides. [...] Heim and his colleagues suggest that the overall effects of ololiuqui are due to these two compounds, the d-lysergic acid amide giving intoxication with strong autonomic side-effects and the d-isolysergic acid amide producing some euphoria, synaesthesia, and altered time experience. Certainly elymoclavine, lysergol, chanoclavine, and ergometrine produce no psychic changes in man (Isbell and Gorodetzky, 1966; Hofmann, 1968), though the first two do produce central excitation in animals (Yui and Takeo, 1958).
  6. 1 2 Heim E, Heimann H, Lukács G (1968). "Die psychische Wirkung der mexikanischen Droge "Ololiuqui" am Menschen" [Psychotomimetic effects of the mexican drug “Ololiuqui”]. Psychopharmacologia (in German). 13 (1): 35–48. doi:10.1007/BF00401617. ISSN   0033-3158.
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