Jump to content

Lysergine

Add links
From Wikipedia, the free encyclopedia

Lysergine
Clinical data
Other names9,10-Didehydro-6,8β-dimethylergoline
ATC code
  • None
Identifiers
  • (6aR,9R)-7,9-dimethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H18N2
Molar mass238.334 g·mol−1
3D model (JSmol)
  • C[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
  • InChI=1S/C16H18N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8,10,15,17H,7,9H2,1-2H3/t10-,15-/m1/s1
  • Key:YOZGACBWDKFAAD-MEBBXXQBSA-N

Lysergine, also known as 9,10-didehydro-6,8β-dimethylergoline, is an ergot alkaloid and serotonin receptor agonist of the ergoline family.[1][2][3] It is a minor constituent of ergot.[1]

Pharmacology

[edit]

Lysergine shows selectivity for activation of the serotonin 5-HT2A receptor over several other closely related serotonin receptors (54-fold over the 5-HT2B receptor, 38-fold over the 5-HT2C receptor, and 127-fold over the 5-HT1A receptor).[2][3] The drug is a partial agonist of the 5-HT2A receptor with moderate intrinsic activity (Emax = 57%).[2][3]

Lysergine activation of serotonin receptors[2][3]
5-HT1A5-HT2A5-HT2B5-HT2C
EC50EmaxEC50EmaxEC50EmaxEC50Emax
342 ± 23ND2.7 ± 1.657%145 ± 5436%103 ± 942%
Notes: EC50 values are nanomolar (nM) and EC50 values are mean ± SEM.[2][3]

An analogue of lysergine, (+)-13-fluorolysergol, is an even more selective agonist of the 5-HT2A receptor than lysergine (EC50 for 5-HT2B and 5-HT2C of >10,000 nM).[2][3] However, this compound has relatively weak maximal efficacy in activating the receptor (Emax = 17%).[2][3]

Chemistry

[edit]

Analogues

[edit]

Isotryptamine or JRT-type analogues of lysergine have been described.[4][5]

See also

[edit]

References

[edit]
  1. 1 2 Kren V (1991). "Bioconversions of ergot alkaloids". Advances in Biochemical Engineering/Biotechnology. 44: 123–144. doi:10.1007/Bfb0000750. ISBN 978-3-540-54094-6. PMID 1781317.{{cite journal}}: CS1 maint: periodical has ISBN (link)
  2. 1 2 3 4 5 6 7 Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123.
  3. 1 2 3 4 5 6 7 Yuan H, Guo Z, Luo T (February 2017). "Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity". Organic Letters. 19 (3): 624–627. doi:10.1021/acs.orglett.6b03779. PMID 28106398.
  4. ↑ Sabnis RW (June 2025). "Novel Desamide Isotryptamine Tetracycles as 5-HT2C Agonists for Treating Brain Disorders". ACS Medicinal Chemistry Letters. 16 (6): 976–977. doi:10.1021/acsmedchemlett.5c00286. PMC 12169470. PMID 40529093.
  5. ↑ WO patent 2025080608, Tuck JR, Olson DE, Basargin AG, Dunlap L, Powell NA, Chytil M, Ghosh M, "Desamide isotryptamine tetracycles for treating brain disorders", published 17 April 2025, assigned to Delix Therapeutics Inc and University of California
Retrieved from "https://en.wikipedia.org/w/index.php?title=Lysergine&oldid=1360858068"