| Width: | 125px |
| Pubchem: | 12312582 |
| Chemspiderid: | 20100727 |
| Unii: | RR1JX77V7F |
| Chembl: | 291097 |
| Synonyms: | 9,10-Didehydro-6,8β-dimethylergoline |
| Iupac Name: | (6aR,9R)-7,9-dimethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline |
| C: | 16 |
| H: | 18 |
| N: | 2 |
| Smiles: | C[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C |
| Stdinchi: | 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 |
| Stdinchikey: | 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.
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). The drug is a partial agonist of the 5-HT2A receptor with moderate intrinsic activity (Emax = 57%).
| 5-HT2C | ||||||||
|---|---|---|---|---|---|---|---|---|
| EC50 | Emax | EC50 | Emax | EC50 | Emax | EC50 | Emax | |
| 342 ± 23 | 2.7 ± 1.6 | 57% | 145 ± 54 | 36% | 103 ± 9 | 42% | ||
| Notes: EC50 values are nanomolar (nM) and EC50 values are mean ± SEM. | ||||||||
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 >10,000nM). However, this compound has relatively weak maximal efficacy in activating the receptor (Emax = 17%).