lysergol

{{Distinguish|Liserdol|Lisuride}}

{{Chembox

| Verifiedfields = changed

| verifiedrevid = 462095111

| ImageFile = Lysergol.svg

| ImageSize = 150px

| IUPACName = (6-Methyl-9,10-didehydroergolin-8β-yl)methanol

| SystematicName = [(6aR,9R)-7-Methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl]methanol

| OtherNames =

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 14267

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 39947

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = BIXJFIJYBLJTMK-MEBBXXQBSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 1413-67-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = NTR684Z1AZ

| PubChem = 14987

| IUPHAR_ligand = 123

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 60528

| SMILES = OC[C@@H]3/C=C2/c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C

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|Section2={{Chembox Properties

| Formula=C₁₆H₁₈N₂O

| MolarMass=254.33 g/mol

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|Section3={{Chembox Hazards

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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 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.{{cite journal|last1=Yuan|first1=Haosen|last2=Guo|first2=Zhixian|last3=Luo|first3=Tuoping|title=Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity|journal=Organic Letters|year=2017|issn=1523-7060|doi=10.1021/acs.orglett.6b03779}}

The binding of lysergol, as well as of isolysergol, to the serotonin 5-HT_1A, 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors has been described.{{cite web | title=Selective psychedelic compounds | website=Google Patents | date=21 June 2022 | url=https://patents.google.com/patent/WO2023018480A1 | access-date=18 March 2025}}{{cite journal | vauthors = Tasker NR, Wipf P | title = A Short Synthesis of Ergot Alkaloids and Evaluation of the 5-HT1/2 Receptor Selectivity of Lysergols and Isolysergols | journal = Org Lett | volume = 24 | issue = 40 | pages = 7255–7259 | date = October 2022 | pmid = 35993579 | doi = 10.1021/acs.orglett.2c02569 | url = }}

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.{{cite book | vauthors = Fanchamps A | chapter=Some Compounds With Hallucinogenic Activity | veditors=Berde B, Schild HO | title=Ergot Alkaloids and Related Compounds | publisher=Springer Berlin Heidelberg | publication-place=Berlin, Heidelberg | date=1978 | isbn=978-3-642-66777-0 | doi=10.1007/978-3-642-66775-6_8 | pages=567–614 | series=Handbook of Experimental Pharmacology (HEP) | volume=49 | chapter-url=https://web.archive.org/web/20250330033128/https://bibliography.maps.org/resources/download/8769#page=30 | quote=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 [...]}}{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | pages = 98–144 | title = Hallucinogenic Agents | date = 1975 | publisher = Wright-Scientechnica | location = Bristol | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1 | quote = 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).}}{{cite journal | vauthors = Heim E, Heimann H, Lukács G | title=Die psychische Wirkung der mexikanischen Droge “Ololiuqui” am Menschen | trans-title=Psychotomimetic effects of the mexican drug “Ololiuqui” | journal=Psychopharmacologia | volume=13 | issue=1 | date=1968 | issn=0033-3158 | doi=10.1007/BF00401617 | pages=35–48 | language=de | url=https://bitnest.netfirms.com/external/10.1007/BF00401617}} It was inactive as a hallucinogen at doses of 2 to 8{{nbsp}}mg orally, up to more than 100{{nbsp}}times the effective dosage of LSD, but did produce light sedative-like effects at the 8{{nbsp}}mg dose.

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).