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Name

Lisuride

IUPAC names

N,N-Diethyl-N′-(6-methyl-9,10-didehydroergolin-8α-yl)urea
N,N-Diethyl-N′-[(6aR,9S)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl]urea
N,N-Diethyl-N′-[(8α)-6-methyl-9,10-didehydroergolin-8-yl]urea
1,1-Diethyl-3-(6-methyl-9,10-didehydroergolin-8α-yl)urea

ID 5082 · Formula C₂₀H₂₆N₄O · Molecular weight 338.447

InChI InChI=1S/C20H26N4O/c1-4-24(5-2)20(25)22-14-10-16-15-7-6-8-17-19(15)13(11-21-17)9-18(16)23(3)12-14/h6-8,10-11,14,18,21H,4-5,9,12H2,1-3H3,(H,22,25)/t14-,18+/m0/s1

InChI Key BKRGVLQUQGGVSM-KBXCAEBGSA-N This stereoisomer Any stereoisomer

SMILES CCN(C(=O)N[C@@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC

ChemSpider 26847
PubChem 28864
Wikidata Q424446
Wikipedia Lisuride

Marona-Lewicka, D; Kurrasch-Orbaugh, DM; Selken, JR; Cumbay, MG; Lisnicchia, JG; Nichols, DE. Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine 1A receptor-mediated behavioral effects overlap its other properties in rats Psychopharmacology, 1 Oct 2002, 164 (1), 93–107. 293 kB. https://doi.org/10.1007/s00213-002-1141-z

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. https://doi.org/10.1016/j.pbb.2007.06.001

Nichols, DE. Potential psychotomimetics: Bromomethoxyamphetamines and structural congeners of lysergic acid Ph. D. Thesis, University of Iowa, Iowa City, IA, 1 May 1973. 13.0 MB. NMR,IR,other

Perez-Aguilar, JM; Shan, J; LeVine, MV; Khelashvili, G; Weinstein, H. A Functional Selectivity Mechanism at the Serotonin-2A GPCR Involves Ligand-Dependent Conformations of Intracellular Loop 2 J. Am. Chem. Soc., 12 Nov 2014, 136 (45), 16044–16054. 4.2 MB. https://doi.org/10.1021/ja508394x

López-Giménez, JF; González-Maeso, J. Hallucinogens and serotonin 5-HT_2A receptor-mediated signaling pathways In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 45-73. 712 kB. https://doi.org/10.1007/7854_2017_478

Halberstadt, AL; Geyer, MA. Effect of hallucinogens on unconditioned behavior In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 159-199. 879 kB. https://doi.org/10.1007/7854_2016_466

Helm, K. Synthese und funktionelle In-vitro-Pharmakologie neuer Liganden des 5-HT_2A-Rezeptors aus der Klasse Ph. D. Thesis, Universität Regensburg, Dresden, 1 Jan 2014. 3.2 MB. #11 LC,MS,NMR,IR

Hoffman, AJ. Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives Ph. D. Thesis, Purdue University, 1 Aug 1987. 9.3 MB. NMR

McCorvy, JD. Mapping the binding site of the 5-HT_2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics Ph. D. Thesis, Purdue University, 1 Jan 2012. 3.9 MB. #Lisuride

Gõrnemann, T; Jähnichen, S; Schurad, B; Latté, KP; Horowski, R; Tack, J; Flieger, M; Pertz, HH. Pharmacological properties of a wide array of ergolines at functional alpha₁-adrenoceptor subtypes N-S. Arch. Pharmacol., 1 Jan 2008, 376 (5), 321–330. 303 kB. https://doi.org/10.1007/s00210-007-0221-3 #Lisuride

Flanagan, TW; Billac, GB; Landry, AN; Sebastian, MN; Cormier, SA; Nichols, CD. Structure–activity relationship analysis of psychedelics in a rat model of asthma reveals the anti-inflammatory pharmacophore ACS Pharmacol. Transl. Sci., 9 Apr 2021, 4 (2), 488-502. 13.3 MB. https://doi.org/10.1021/acsptsci.0c00063 #lisuride

Dong, C; Ly, C; Dunlap, LE; Vargas, MV; Sun, J; Hwang, I; Azinfar, A; Oh, WC; Wetsel, WC; Olson, DE; Tian, L. Psychedelic-inspired drug discovery using an engineered biosensor Cell, 13 May 2021, 184 (10), 2779-2792.e18. 8.3 MB. https://doi.org/10.1016/j.cell.2021.03.043 #LIS NMR

Cumming, P; Scheidegger, M; Dornbierer, D; Palner, M; Quednow, BB; Martin-Soelch, C. Molecular and functional imaging studies of psychedelic drug action in animals and humans Molecules, 1 Jan 2021, 26 (9), 2451. 3.5 MB. https://doi.org/10.3390/molecules26092451 #21

Halberstadt, AL. Recent advances in the neuropsychopharmacology of serotonergic hallucinogens Behav. Brain Res., 15 Jan 2015, 277, 99–120. 4.1 MB. https://doi.org/10.1016/j.bbr.2014.07.016 #Lisuride

Kurrasch-Orbaugh, DM. Elucidation of the serotonin 5-HT_2A receptor-coupled phospholipase A₂ signaling pathway Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 May 2002. 7.9 MB. #Lisuride

Fantegrossi, WE; Murnane, KS; Reissig, CJ. The behavioral pharmacology of hallucinogens Biochem. Pharmacol., 1 Jan 2008, 75 (1), 17–33. 359 kB. https://doi.org/10.1016/j.bcp.2007.07.018 #Lisuride

Duan, W; Cao, D; Wang, S; Cheng, J. Serotonin 2A receptor (5-HT_2AR) agonists: Psychedelics and non-hallucinogenic analogues as emerging antidepressants Chem. Rev., 10 Jan 2024, 124 (1), 124–163. 12.6 MB. https://doi.org/10.1021/acs.chemrev.3c00375 #71

Pyrroguride

7 Dec 2019 · · Isomer Design