Exploring N-Butan-2-yllysergamide. To explore a different substance…

Names:
LSB
2-Butyllysergamide
N-Butan-2-yllysergamide
Lysergic acid 2-butyl amide
IUPAC name:
(8β)-N-(Butan-2-yl)-6-methyl-9,10-didehydroergoline-8-carboxamide
5315 · C20H25N3O · 323.432
InChI=1S/C20H25N3O/c1-4-12(2)22-20(24)14-8-16-15-6-5-7-17-19(15)13(10-21-17)9-18(16)23(3)11-14/h5-8,10,12,14,18,21H,4,9,11H2,1-3H3,(H,22,24)/t12?,14-,18-/m1/s1
NYFSQPDQLFFBRA-OLTOQGTGSA-N This stereoisomer Any stereoisomer
CCC(NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)C

Meyers-Riggs, B. Non-LSD ergoloids. countyourculture, countyourculture: rational exploration of the underground, 1 Dec 2011.

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Oberlender, R; Pfaff, RC; Johnson, MP; Huang, X; Nichols, DE. Stereoselective LSD-like activity in d-lysergic acid amides of R- and S-2-aminobutane. J. Med. Chem., 1 Jan 1992, 35 (2), 203–211. 1.1 MB. https://doi.org/10.1021/jm00080a001

Watts, VJ; Mailman, RB; Lawler, CP; Neve, KA; Nichols, DE. LSD and structural analogs: Pharmacological evaluation at D1 dopamine receptors. Psychopharmacology, 1 Apr 1995, 118 (4), 401–409. 1.4 MB. https://doi.org/10.1007/BF02245940

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

Nichols, DE. Structure-activity relationships of serotonin 5-HT2A agonists. WIREs Membr. Transp. Signal, 1 Sep 2012, 1 (5), 559-579. 573 kB. https://doi.org/10.1002/wmts.42

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 #25

LSD
N-Butyllysergamide
LAMPA · LMP
MIPLA
l-LSD
d-iso-LSD
l-iso-LSD
(S)-LSB
(R)-LSB
18 October 2018 · Creative Commons BY-NC-SA ·