Lysergine
{{Short description|Ergot alkaloid and serotonin receptor agonist}}
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| CAS_number = 519-10-8
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| PubChem = 12312582
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| ChemSpiderID = 20100727
| UNII = RR1JX77V7F
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| ChEMBL = 291097
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| 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
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Lysergine, also known as 9,10-didehydro-6,8β-dimethylergoline, is an ergot alkaloid and serotonin receptor agonist of the ergoline family.{{cite journal | vauthors = Kren V | title = Bioconversions of ergot alkaloids | journal = Adv Biochem Eng Biotechnol | volume = 44 | issue = | pages = 123–144 | date = 1991 | pmid = 1781317 | doi = | url = }}{{cite journal | vauthors = Duan W, Cao D, Wang S, Cheng J | title = Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants | journal = Chem Rev | volume = 124 | issue = 1 | pages = 124–163 | date = January 2024 | pmid = 38033123 | doi = 10.1021/acs.chemrev.3c00375 | url = }}{{cite journal | vauthors = Yuan H, Guo Z, Luo T | title = Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity | journal = Org Lett | volume = 19 | issue = 3 | pages = 624–627 | date = February 2017 | pmid = 28106398 | doi = 10.1021/acs.orglett.6b03779 | url = }} It is a minor constituent of ergot.
Pharmacology
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%).
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| colspan="2" | 5-HT1A | colspan="2" | 5-HT2A | colspan="2" | 5-HT2B | colspan="2" | 5-HT2C | ||||
|---|---|---|---|---|---|---|---|
| EC50 | Emax | EC50 | Emax | EC50 | Emax | EC50 | Emax |
| 342 ± 23 | {{Abbr|ND|No data}} | 2.7 ± 1.6 | 57% | 145 ± 54 | 36% | 103 ± 9 | 42% |
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| colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;" | 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 >10,000{{nbsp}}nM). However, this compound has relatively weak maximal efficacy in activating the receptor (Emax = 17%).
See also
References
{{Reflist}}
{{Authority control|qid=Q27896545}}
{{Serotonin receptor modulators}}
{{Ergolines}}