Explore N-Pentan-2-yllysergamide | TiHKAL · info

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Names

2-LSP
N-Pentan-2-yllysergamide
2-APLA

IUPAC names

6-Methyl-N-(pentan-2-yl)-9,10-didehydroergoline-8β-carboxamide
(6aR,9R)-7-Methyl-N-(pentan-2-yl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
(8β)-6-Methyl-N-(pentan-2-yl)-9,10-didehydroergoline-8-carboxamide

ID 5318 · Formula C₂₁H₂₇N₃O · Molecular weight 337.459

InChI InChI=1S/C21H27N3O/c1-4-6-13(2)23-21(25)15-9-17-16-7-5-8-18-20(16)14(11-22-18)10-19(17)24(3)12-15/h5,7-9,11,13,15,19,22H,4,6,10,12H2,1-3H3,(H,23,25)/t13?,15-,19-/m1/s1

InChI Key JGLCNUHMSLNTLJ-NWLOPNIYSA-N This stereoisomer Any stereoisomer

SMILES CCCC(NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)C

ChemSpider 23240517
PubChem 44384967

TiHKAL #26 LSD

Nichols, DE; Monte, A; Huang, X; Marona-Lewicka, D. Stereoselective pharmacological effects of lysergic acid amides possessing chirality in the amide substituent Behav. Brain Sci., 15 Dec 1995, 73 (1–2), 117–119. 267 kB. https://doi.org/10.1016/0166-4328(96)00080-0

Monte, AP; Marona-Lewicka, D; Kanthasamy, A; Sanders-Bush, E; Nichols, DE. Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes J. Med. Chem., 1 Mar 1995, 38 (6), 958–966. 1.2 MB. https://doi.org/10.1021/jm00006a015 #3a,b MS,NMR,IR,TLC,other

Nichols, DE. Structure-activity relationships of serotonin 5-HT_2A agonists WIREs Membr. Transp. Signal, 1 Sep 2012, 1 (5), 559-579. 573 kB. https://doi.org/10.1002/wmts.42 #18

Nichols, DE. Chemistry and structure–activity relationships of psychedelics In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 1-43. 2.6 MB. https://doi.org/10.1007/7854_2017_475 #26

Nichols, DE. LSD and its lysergamide cousins Heffter Rev., 1 Jan 2001, 2 (6), 80–87. 265 kB.

Heim, R. Synthesis and pharmacology of potent 5-HT_2A receptor agonists with N-2-methoxybenzyl partial structure SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. 3.9 MB. #26 In German. MS,NMR,IR

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. #2-APLA

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7 Dec 2019 · · Isomer Design