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Lysergine - Wikipedia

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Lysergine
Clinical data
Other names9,10-Didehydro-6,8β-dimethylergoline
Identifiers

  • (6aR,9R)-7,9-dimethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline

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]

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-HT1A 5-HT2A 5-HT2B 5-HT2C
EC50 Emax EC50 Emax EC50 Emax EC50 Emax
342 ± 23 ND 2.7 ± 1.6 57% 145 ± 54 36% 103 ± 9 42%
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]

  1. ^ a b Kren V (1991). "Bioconversions of ergot alkaloids". Adv Biochem Eng Biotechnol. 44: 123–144. PMID 1781317.
  2. ^ a b c d e f g Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123.
  3. ^ a b c d e f g Yuan H, Guo Z, Luo T (February 2017). "Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity". Org Lett. 19 (3): 624–627. doi:10.1021/acs.orglett.6b03779. PMID 28106398.