View source for Lysergol

{{Distinguish|Liserdol|Lisuride}}
{{Chembox
| Verifiedfields = changed
| verifiedrevid = 462095111
| ImageFile = Lysergol.svg
| ImageSize = 150px
| IUPACName = (6-Methyl-9,10-didehydroergolin-8β-yl)methanol
| SystematicName = [(6a''R'',9''R'')-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
}}
|Section2={{Chembox Properties
| Formula=C<sub>16</sub>H<sub>18</sub>N<sub>2</sub>O
| MolarMass=254.33 g/mol
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
  }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
}}

'''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 [[Psychedelics, dissociatives and deliriants|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.<ref name="YuanGuo2017">{{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}}</ref>

The binding of lysergol, as well as of [[isolysergol]], to the [[serotonin]] [[5-HT1A receptor|5-HT<sub>1A</sub>]], [[5-HT2A receptor|5-HT<sub>2A</sub>]], [[5-HT2B receptor|5-HT<sub>2B</sub>]], and [[5-HT2C receptor|5-HT<sub>2C</sub> receptor]]s has been described.<ref name="WO2023018480A1">{{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}}</ref><ref name="TaskerWipf2022">{{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 = }}</ref>

In contrast to LSD and other lysergamides, lysergol is non-[[hallucinogen]]ic in humans and is described as not contributing to the hallucinogenic effects of morning glory seeds.<ref name="Fanchamps1978">{{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 [...]}}</ref><ref name="BrimblecombePinder1975">{{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).}}</ref><ref name="HeimHeimannLukács1968">{{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| url-access=subscription }}</ref> It was inactive as a hallucinogen at doses of 2 to 8{{nbsp}}mg [[oral administration|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.<ref name="Fanchamps1978" /><ref name="HeimHeimannLukács1968" />

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 ==
* [[Lysergine]]
* [[Lysergic acid]]
* [[Descarboxylysergic acid]]
* [[Isoergine]]

==References==
{{Reflist}}

== External links ==
*  [http://www.erowid.org/plants/mushrooms/references/other/1971_hofmann_bulletin-narcotics.shtml  Hoffman, A. ''Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico'' Bulletin on Narcotics 1971 1 3]
* [https://web.archive.org/web/20050325195826/http://www.psychedelic-library.org/eleusis/mixing%20the%20kykeon%20final%20draft.pdf Mixing the kykeon -- P. Webster, D. M. Perrine & C.A.P. Ruck]
* [http://www.erowid.org/library/books_online/tihkal/tihkal26.shtml TiHKAL (A & A Shulgin) #26]
* [http://www.erowid.org/chemicals/lsa/lsa.shtml Erowid's LSA Vault]

{{Serotonin receptor modulators}}
{{Ergolines}}

[[Category:Ergot alkaloids]]
[[Category:Serotonin receptor agonists]]