Exploring LA-SS-Az. To explore a different substance…

Names:
LA-SS-Az · LSZ · Lysergic acid 2,4-dimethylazetidide
IUPAC name:
[(2R,4R)-2,4-Dimethylazetidin-1-yl][(8β)-6-methyl-9,10-didehydroergolin-8-yl]methanone
ID: 5363 · Formula: C21H25N3O · Molecular weight: 335.443
InChI: InChI=1S/C21H25N3O/c1-12-7-13(2)24(12)21(25)15-8-17-16-5-4-6-18-20(16)14(10-22-18)9-19(17)23(3)11-15/h4-6,8,10,12-13,15,19,22H,7,9,11H2,1-3H3/t12-,13-,15+,19+/m0/s1

Brandt, SD; Kavanagh, PV; Twamley, B; Westphal, F; Elliott, SP; Wallach, J; Stratford, A; Klein, LM; McCorvy, JD; Nichols, DE; Halberstadt, AL. Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775). Drug Test. Analysis, 27 Jul 2017, n/a-n/a. 1.2 MB. http://dx.doi.org/10.1002/dta.2222

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB.

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. http://dx.doi.org/10.1371/journal.pone.0009019

Nichols, DE; Frescas, SP; Marona-Lewicka, D; Kurrasch-Orbaugh, DM. Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). J. Med. Chem., 1 Jan 2002, 45 (19), 4344–4349. 268 kB. http://dx.doi.org/10.1021/jm020153s

Brandt, SD; Kavanagh, PV; Westphal, F; Elliott, SP; Wallach, J; Colestock, T; Burrow, TE; Chapman, SJ; Stratford, A; Nichols, DE; Halberstadt, AL. Return of the lysergamides. Part II: Analytical and behavioural characterization of N6-allyl-6-norlysergic acid diethylamide (AL-LAD) and (2′S,4′S)-lysergic acid 2,4-dimethylazetidide (LSZ). Drug Test. Analysis, 1 Jan 2017, 9 (1), 38-50. 1.6 MB. http://dx.doi.org/10.1002/dta.1985 Open access DOI

Wacker, D; Wang, S; McCorvy, JD; Betz, RM; Venkatakrishnan, AJ; Levit, A; Lansu, K; Schools, ZL; Che, T; Nichols, DE; Shoichet, BK; Dror, RO; Roth, BL. Crystal Structure of an LSD-Bound Human Serotonin Receptor. Cell, 26 Jan 2017, 168 (3), 377–389.e12. 5.4 MB. http://dx.doi.org/10.1016/j.cell.2016.12.033 Open access DOI

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

Chapman, SJ; Burns, D; Burrow, TE. 1H and 13C NMR spectra of (2′S,4′S)-lysergic acid 2,4-dimethylazetidide (LSZ). BLOTTER, 15 Jul 2016, 2 (2). 24.9 MB. http://dx.doi.org/10.16889/isomerdesign-4 Open access DOI

LA-111
Isoergine
12-MeO-6-Me-Ergoline
5705
5707
6-Me-Ergoline
5279
Descarboxylysergic acid
LA-RR-Az
LA-RS-Az
LA-Pip
MPD-75
LA-111
Isoergine
12-MeO-6-Me-Ergoline
5705
5707
6-Me-Ergoline
5279
Descarboxylysergic acid
LA-RR-Az
LA-RS-Az
LA-Pip
MPD-75
13 December 2017 · Creative Commons BY-NC-SA ·