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]
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 8mgorally, up to more than 100times the effective dosage of LSD, but did produce lightsedative-like effects at the 8mg dose.[4][6]
Lysergol is not acontrolled substance in theUnited 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 toLSD, which is a controlled substance. However, lysergol is an intermediate in the manufacture of some ergoloid medicines (e.g.,nicergoline).
^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.ISSN1523-7060.
^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.PMID35993579.
^abFanchamps 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.ISBN978-3-642-66777-0.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 [...]
^Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds".Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144.ISBN978-0-85608-011-1.OCLC2176880.OL4850660M.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).
