Exploring AL-LAD. To explore a different substance…

Names:
AL-LAD
N-Allyl-nor-LSD
9,10-Didehydro-6-allyl-N,N-diethylergoline-8β-carboxamide
N-(6)-Allylnorlysergic acid, N,N-diethylamide
6-Norlysergamide, 6-allyl-N,N-diethyl
6-Norlysergic acid, 6-allyl-N,N-diethylamide
6-Allyl-N,N-diethyl-6-norlysergamide
N,N-Diethylnorlysergamide, 6-allyl
IUPAC name:
(8β)-N,N-Diethyl-6-(prop-2-en-1-yl)-9,10-didehydroergoline-8-carboxamide
5001 · C22H27N3O · 349.469
InChI=1S/C22H27N3O/c1-4-10-25-14-16(22(26)24(5-2)6-3)11-18-17-8-7-9-19-21(17)15(13-23-19)12-20(18)25/h4,7-9,11,13,16,20,23H,1,5-6,10,12,14H2,2-3H3/t16-,20-/m1/s1
JCQLEPDZFXGHHQ-OXQOHEQNSA-N This stereoisomer Any stereoisomer

Hoffman, AJ; Nichols, DE. Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives. J. Med. Chem., 1 Jan 1985, 28 (9), 1252–1255. 583 kB. https://doi.org/10.1021/jm00147a022

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

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. https://doi.org/10.1002/dta.1985 Open access DOI

Chapman, SJ; Burns, D; Burrow, TE. 1H and 13C NMR spectra of N6-allyl-6-norlysergic acid diethylamide (AL-LAD). BLOTTER, 15 Jul 2016, 2 (1). 23.7 MB. https://doi.org/10.16889/isomerdesign-3 Open access DOI

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. https://doi.org/10.1002/dta.2222

Stachulski, AV; Nichols, DE; Scheinmann, F. Stereochemical and NMR reassignment of 6-norlysergic acid diethylamide and 6-nor-6-allyllysergic acid diethylamide. J. Chem. Research (S), 1 Jan 1996, 30–31. 4.0 MB.

EMCDDA. New drugs in Europe, 2015, European Monitoring Centre for Drugs and Drug Addiction, 1 May 2016. 1.0 MB. #28

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. 652 kB. https://doi.org/10.1007/7854_2016_466

Nichols, DE. Psychedelics. Pharmacol. Rev., 1 Apr 2016, 68 (2), 264-355. 1.9 MB. https://doi.org/10.1124/pr.115.011478 Updated with published correction to Figure 4 (the α-methyl group was missing in the original)

Nichols, DE. Dark classics in chemical neuroscience: Lysergic acid diethylamide (LSD). ACS Chem. Neurosci., 20 Feb 2018, n/a. 1.1 MB. https://doi.org/10.1021/acschemneuro.8b00043

Shulgin, AT. Basic Pharmacology and Effects. In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 2003; pp 67–137. 6.3 MB.

Jacob, P; Shulgin, AT. Structure-activity relationships of the classic hallucinogens and their analogs. In Hallucinogens: An update. NIDA Research Monograph 146; Lin, GC; Glennon, RA, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1994; pp 74–91. 51 kB.

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. #6

CYP-LAD
LA-Cispyr
N-Cyclohexyllysergamide
4-Methyl-N-({1-[2-(morpholin-4-yl)ethyl]-1H-indol-3-yl}methyl)aniline
CUMYL-P7AICA
CUMYL-PINACA
LA-Azepane
19 September 2018 · Creative Commons BY-NC-SA ·